You Keep Saying Math Teachers Should Have Taught You These Things, continued

I recently wrote a piece about the trend of adults expressing desires that their high school math teachers should have taught them valuable life lessons. I tried to fix this and it turns out that now that you’re not in my classroom you actually want me to teach you something. 

Better late than never, I guess, but please at some point can we return to how cool math can be?



If you’re a younger Millenial or a Gen Z who is about to enter the workforce, you’ve been existing in one of three buckets: knowing what’s happening in HR presentations about health insurance, pretending to know what’s happening in HR presentations or you’ve never sat in on an HR presentation. You probably want a better idea of what’s happening so I will try to give you a solid foundation.

Up until the age of 30, the only thing I knew about health insurance was that it was the barometer for if the job was good or not. Coming out of college people would say things like, “I got a job with full insurance and benefits.” Everyone would respond with, “Wow. Yes. V Adult. That’s so good. You can get off your parents plan now.” 

Somehow, getting out from under the parent’s thumb seems so punk rock. 

But let’s back it up for a second. Not everyone is on their parent’s plan. Some people have no idea what their health care options were as children. Maybe you were on CHIP or maybe your parents were bought in through the Affordable Care Act (ACA). Maybe the school nurse was your doctor. But I hope now that you have the ability to provide your own insurance and it’s OK if you’re confused. Let’s cover some basics. 

Getting off your parents plan

Ok so you graduated and got a job. You were paid a good salary. You got a 1-bedroom apartment in the coolest part of town. You didn’t need to crash with your parents for a bit or sell a bike for $100 on Craigslist that you bought for $20 earlier that day at Goodwill (I did this only once.) And you definitely don’t need to stay on your parent’s plan. 

Because of ACA, it was recognized that very few young people have the aforementioned experience in an excellent gig right away. You can stay on your parent’s plan until you are 26. You can stay on their plan even if you have a job that provides insurance. For the sake of this article let’s say you have a job that offers health insurance but you don’t want to look like a total rookie when comparing plans. I can’t tell you what a good plan is but I can equip you with some basic knowledge so that you can ask good questions and figure out your situation. 

Insurance is best explained by the following scenario. Let’s say there are ten rural farmers in an area. One of the farmer’s barns burns to the ground after getting struck by lightning. The family only has enough money to rebuild half the barn so they’re screwed. The surrounding farmers decide to chip in and help them out knowing that the local support would do the same for them if any other disaster happened. Then one farmer thinks to themselves, “You know, we could all pitch in $100 a month and then if anything bad happens to any of us, we can just go to that pool of money and know that we’d be taken care of. We could ensure that we’d be OK and we can call it to be insured.” That’s kind of how it works. And in fact, big companies like USAA and Navy Federal got their start this way. Military folks overseas would sometimes have a hard time finding coverage for family members for things like car insurance so a bunch of them got together and said, “we’ll do it on our own!” So punk rock. Insurance is usually applied to individual things like home, car, or health. A lot of the terminology is the same. 

When learning about insurance plans you see a few words tossed around like everyone knows them. And no one ever really explains what they are to the person who has never learned about healthcare plans. You just slowly piece together what is good and bad by whatever the older people complain about. “I can’t believe how much our premiums went up.” A premium sounds like a good thing. Like, “wow yes my premium is so prime I’m so good.” But the tone of discussing premiums is usually negative so then you’re all, “So do I want my premium to be low?” The insurance premium is the cost to you each month to have that plan. For the farmers above their monthly premium was $100. Whether a premium is good or bad is subjective. If the product remains the same but gets more expensive, then you’d be annoyed. That’s often what happens that causes people to groan. 

“But Plan A has a lower deductible.” I heard this phrase for multiple years and no power of deduction helped me figure out what the hell people were talking about. The deductible is the amount paid out of pocket by you before an insurance provider will fully pay any expenses. So if your deductible goes up that means you have to pay more before you get help. For our farmers above, they could have agreed that the deductible was $500. Your barn partially burns down and it only requires $300 to fix it. The Farmer Insurance group says they’ll make a note of the incident but not help you just yet. For your health insurance this number is usually anywhere from $1500 to $6000. Which leads us to why would you have a low deductible or a high deductible.

Low Deductible Health Care Plans, LDHP, means you don’t have to pay a ton of money before the insurance will fully kick in. Why wouldn’t you default to this? Well typically it costs more money in the range of $50 to $100 more per month (or even more depending on if you’re an individual buying insurance or getting it through your job). So this is the trade off. You are paying $1200 more per year in order to possibly cover yourself in case you need it. If you ended up not really even going to the doctor for a year then you basically overpaid $1200. THIS IS HOW INSURANCE COMPANIES MAKE MONEY. They want you to buy more than what you need and then cover you for as little as possible. LDHP come with a copay which means that when you go see a doctor there is a predetermined amount that you pay. There is little guesswork and it’s convenient. 

High Deductible Health Care Plans, HDHP, means you have to pay a lot more money for healthcare before insurance fully kicks in. Why would you want to pay a lot more money? Two reasons: you are healthy and you want tax savings. If you are healthy that might mean you don’t have regularly scheduled doctor’s appointments, prescriptions, etc. So if you may not need insurance an HDHP can save you money. The more interesting reason to get an HDHP is the tax savings. Let’s say you can afford the higher monthly payment of the low deductible plan but you are healthy and want the low deductible plan. The extra $100 per month that you would have paid for the low deductible can be put in a health savings accounts (HSA). Your HSA is literally a savings account that you can draw money from for any health related expense. Often companies will put money into this account for you. So not only can you put the $100 a month into the HSA to cover any expenses, it’s also done pre-tax

Quick lesson on pre-tax. First refer back to my previous article where I discuss tax brackets. Now for this example, let’s say that you are on the cusp of the 22% and 24% brackets. You make $86,000 per year which puts you $475 into the 24% tax bracket. That means of the $475, the government takes 24% or $114 and you’re left with $361. Now let’s say that you put that $475 into your HSA. You aren’t taxed on it. You get to keep all $475 and put it towards healthcare. And because it’s a savings account you can earn interest and continue to put money away for the rest of your life. 

This next section is kind of advanced but where the long term impacts really mean something. 

HSA vs 401K. When you put money into a 401k or an IRA, you get the tax deduction in the short term but you then pay taxes on it later in life when you do a withdrawal. So either you’re taxed now or taxed later. But with an HSA you are never taxed when the money is used for healthcare. Show me a person that doesn’t spend incrementally more money on healthcare as they age. 

There is of course way more to this and it’s worth speaking to your HR representative to cover your unique situation and what’s best for you. Talk to a financial planner to figure out what to do with expendable income. Take these explanations as your starting point for making decisions about the rest of your life. Because after all, I’m not an expert. I was your math teacher.

You Keep Saying Math Teachers Should Have Taught You These Things, Let’s Get it Over With

Okay. I get it.

Math teachers failed you.

I failed you.

You’re now an adult and realizing that the quadratics are worthless. In my defense, it’s a fundamental cornerstone of mathematics and physics. But, here you are. Here we are.

You keep posting on social media about how your math teachers never taught you about mortgages or taxes. Both of these things are about money.

Money is represented with numbers.

I was responsible for teaching you about numbers.

Therefore I failed you.

Well, guess what?

Here you go.

First: Mortgages.

If you pay rent, then you’re likely helping to pay someone’s mortgage. A mortgage is a homeowner’s monthly payment towards their loan for a house. A house costs a lot of money. And most of us can’t afford to pay for a house with cash because it’s not 1955 and we didn’t exit the Army with a salary that supports a family of four. When people refer to their “mortgage,” they’re usually referring to their escrow, which is made up of three parts: a home loan, home insurance, and property taxes.

The home loan is the amount you borrow to buy the house. The loan repayment has two parts: the interest and the principal. I’m not going to explain how interest works because we definitely covered this in math class and it’s not my fault you barely passed, you lazy piece of sh*t. I will say this: A lot of people wonder what their credit score is or why it matters. The better your credit score, the lower your interest rate is set. It’s a number that reflects how responsible or trustworthy you are with debt. The lower your score, the higher the interest rate, which leads to a higher monthly payment. The higher the payment, the harder it is for you to save. Ever wondered how our system makes it difficult to climb the financial ladder?

Home insurance covers you in case something bad happens. For example, if there’s a hail storm and it irreparably messes up your roof, your insurance company will pay for you to get a new roof. Insurance never covers as much as you think it does, so when something bad does happen, you say to yourself, “Hey! What the hell? I thought this is what insurance is for? I would have rather saved that money and paid for my new roof with that savings!” Except insurance is mandatory, so it’s a racket. Sorry.

Property taxes are an extra payment rate set by your local government. The more your house is worth, the more you pay in taxes. Who decides how much your property is worth? Your local government. Welcome to the wonderful world of conspiracy theories surrounding property values. What do taxes go to? Oh, just things like schools and public infrastructure. Sometimes there is a local initiative to build a new public park — your taxes pay for that. Don’t have kids that use the public schools? Too bad, your taxes will still go to that. If our schools were funded better, I wouldn’t have had to drive Uber on weekends.

And that’s what an escrow is. More valuable than trigonometry? You be the judge.

Second: Filing Taxes

Taxes 101: How to File Taxes

Every year, sometime around February through April, you’ll get some tax forms in the mail from your employer, student loans, banks, and anywhere else you’re connected to the exchange of payments or income. Keep these forms in a safe place. They are not junk mail. Go to TurboTax. Fill out the free form (unless you have a reason to pay for the advanced options, which they will walk you through). Click submit on the forms.

Bam — you’ve done your taxes.

Important advice here!!! Be aware of whether taxes are taken out of your paycheck. If they aren’t, you need to save upwards of 25% of your income to make sure you can pay taxes on it later. A lot of folks think the extra $500 they make a month driving for Lyft is great, but the government is expecting you to cough up some of that money come tax day. In today’s gig economy, this is critical knowledge. Here’s more information on that.

Taxes 201: Advanced Taxes

It isn’t what you think. Ever heard of tax brackets? You know that thing where people say, “Well yah, I got a raise, but now I just pay more in taxes”? Besides being ungrateful, they’re also most likely misinformed.

The United States has a tiered tax rate, rather than a fixed tax rate. A fixed tax rate would mean every dollar you make is taxed at the same rate for everyone. It’s a controversial political topic. If you’re a millionaire you’d pay the same rate as someone on minimum wage. You can form your own opinion about how it should be done.

The tax rate we do have, a tiered tax rate, is poorly understood. Many people think that if they make more money, they move into the next bracket. For example, let’s say you make $84,000. The current tax bracket for that is 22%. You get a raise! Congrats! You now make $85,000 and your tax rate is 24%. People think that your first situation means you paid 22% of $84,000 or $18,480 in taxes and then 24% of $85,000 or $20,400 in the second situation. Effectively they think the $1000 raise mean they paid $1920 more in taxes, netting them a loss of $920. That’s simply not how it works. Instead of doing a longer write up here, just watch this 2:48 long video made by Vox. In short, the $1000 raise means that the extra $1000 was taxed at 24% instead of 22%. So the government took $240 of the $1000 instead of $220, and the rest of their income ($84,000) is taxed exactly the same way it was taxed before.

But how does this apply to your life? Now that you know how income taxes work, you are allowed to shake your fist during tax season with power.

So there you have it. All your resentment against math teachers can just melt away. Now, if only your English teacher taught you how to use a f*cking semicolon.

Arrival Fallacy Awareness

A couple of weeks ago a great friend and mentor of mine shared a New York Times article with me that introduced formal words to a familiar concept. Arrival fallacy is the notion that we delude ourselves into believing we’ll be happier once future goals have been accomplished. This is something that I felt in my professional career, financial situations, and in my own athletic achievements. 

When I first started running I signed up for a marathon and I swear that I didn’t know it was 26.2 miles. Don’t get me wrong. I knew a marathon was far. But as a beginner, what did it matter if it was 20 or 26 miles? My first marathon was a slog-fest. It was an unusually cold day in November in Texas and I started in the back of the pack. I was 24 and jogging alongside retired women. I came in at 5 hours 26 minutes or somewhere around 12 minutes 26 seconds per mile. I worked hard over the next few years, got a coach, ran a few more races, and got my time down to 2 hours 59 minutes or 6 minutes 51 seconds per mile. I was incredibly proud to make that progression over three years. But honestly, I was just as happy with my 5 hour marathon as I was my 3 hour. The happiness came from the journey and not the destination. But about the time things got really serious with running, I got injured. I was supposed to run the 2013 Boston Marathon and all races since felt a bit empty.

It’s much easier to avoid arrival fallacy in terms of hobbies than our professional careers. Hobbies can be choices that come and go. Our professional lives are often more closely tied to our identities. And if we work incredibly hard on becoming a thing, then become that thing, we need to be critical of what we actually accomplished. 

Some words of advice that contradicts a majority of what I write about but addresses the elephant in the room:

  1. If more money isn’t going to solve any problems, then you aren’t going to be any happier. According to a Purdue University study “we find that satiation occurs at $95,000 for life evaluation and $60,000 to $75,000 for emotional well-being. However, there is substantial variation across world regions, with satiation occurring later in wealthier regions.” If the promotion or new job is just more icing on the cake, you’ll realize that you don’t need more sugar on your cake. If the new money allows you to pay off debts faster, solve stressful situations, or allow you to actually have an emergency savings fund, then yes, money will change your life. And that’s a beautiful thing. But if you’re fortunate enough to have an end in sight, once it changes your life and the debt is paid off, your life will level set and you’ll default to something like “I heard something once about the two happiest days of someone’s life are when you buy a boat and.. well, um.. I can’t remember how it ends. Let’s go buy a boat.”

  2. You are not your career. Americans love to ask people, “So Sam, what do you do?” It’s no wonder we get excited at our new jobs and get to tell people what we now “do”. But any new title or career pivot will have its own arrival fallacy and we’ll think, “I worked so hard for this promotion and all I got were new business cards.” I’ve made it a personal quest to not ask people about their careers and instead ask “So what’s your deal? What do you like to do?” You might be a VP of Sales but the fact that you wake up at 4 am every day to do jiu jitsu is actually the topic of conversation I want to discuss. “So what happens if you get choked out before work?”

  3. Changing your circumstance isn’t going to automatically change your happiness. My favorite manager taught me a thought exercise that I will briefly summarize. Circumstances are the events that occur around us. They’re true statements. We can’t change them. However, we are not immune to them and they do cause a reaction in us. And that’s when we can start to take control of what happens next. In short, our mental process to evaluate a circumstance will lead to a result that reinforces our thoughts. It’s somewhat of a self-fulfilling prophecy concept. The reason it’s relevant here is that if you are unhappy with circumstances in your job and a new job completely changes the circumstances (ie a toxic work environment), then you’ll most likely arrive at your new place and not look back. It’s not arrival fallacy. It’s improving your life. But, if the negative things you want to change are actually stemming from your own thoughts, feelings, actions, and results, then you’ll land back in the same place- finding ways to spin circumstances against you. This is where it’s important to do an audit of the things you want to be different. 


Knowing what you’re aiming for and being aware that more money, bigger titles, or new environments may not equate to happiness is critical to well, happiness. At various points in the last 3 years, while walking our dogs and planning our life, my wife and I would make casual references to what would be our next step once our careers “took off”. We never really talked about how we’d know when that was. A month ago we used that phrasing again and my wife stopped us.

“We’ve already taken off. Let’s just take some time to enjoy it.”

Knowing the arrival fallacy is just as important as simply knowing you’ve arrived. We’ve created a culture of constantly setting goals and convincing ourselves that if we aren’t struggling or punishing ourselves then we aren’t growing. But that’s a post for next week.

Knowing when to Jump Ship

I’ve been thinking a lot about how someone is supposed to know when to jump ship. There are currently a lot of these questions floating around in my family and friend group. Relationships and careers are similar in this way. At some point you wake up two years into it and realize that something has changed. So, you do what everyone does in 2019; you secretly change your status on a few apps (Tinder or LinkedIn), pack a bag, change your number, find someone new, and tell all your friends about how much better you are now that you made the change and you just really got to “know yourself” through it all. But really the jump ship/ghosting culture leaves us with one really important question. How do I know when it’s time to leave?

  1. “I’ve stopped growing.”

This one is really important. I’m starting here because it really is the most critical. In relationships this is when someone stops challenging you and the option to coast means you’re wasting time. In careers it means the company has stopped challenging you and the option to coast means you’re wasting your time. This is the type of realization that feels like it pops out of nowhere because it so slowly creeps in that the only way to catch it is to basically have it pointed out. This feeling shares a flat with comfort. But complacency and comfort are two different things. It’s also important to ask yourself,

“Do I feel like I’ve stopped growing only because nothing is new?”

I had a dear friend challenge me once on this. I’m a habitual goal setter. She questioned if just because I had accomplished all my goals, was I really done being challenged? She was right. I wasn’t done. 

So what are your options when you get here? In both relationships and careers, speak up. If you want to be challenged sometimes you have to ask to be challenged. The world around you might be viewing the partnerships as comfortable while you’re feeling complacent. If, and only if, you’ve asked your counterpart to give you more and they can’t, then it’s time to look elsewhere.

  1. “I have nowhere to go from here.” 

Sometimes a job or relationship simply runs its course. It was never going to be anything more than a year or two. In relationships, this is when the person definitely doesn’t want to get serious. In careers, this is when the company can’t get more serious. There is no upward mobility. You’ve maxed out earning potential. You’ve maxed out promotion tracks. And in order to get the types of experiences you need, it requires you to jump ship. 

This is subtly different than not having room to grow. You can not have a promotion opportunity but still have room to grow. You can possibly get promoted to a role that theoretically teaches you nothing new. The missing question here must come from you. What are you trying to do? 

  1. “The house is on fire but everything is fine.”

The most obvious reason to jump ship is when the toxic work environment seeps into your skin and can’t be washed off. In relationships, this is when nothing seems to go right, you’re walking on eggshells, and you’d rather be at work than in the relationship. In careers, this is when nothing seems to go right and you’re rather be working from home. What’s most fascinating about our human psychology is that we’re really resilient creatures when in toxic scenarios. We all of a sudden turn into really forgiving and trusting people. We give more time for change. I like to use the Steve Jobs quote from his famous 2005 Stanford commencement speech. “For the past 33 years, I have looked in the mirror every morning and asked myself: ‘If today were the last day of my life, would I want to do what I am about to do today?’ And whenever the answer has been ‘No’ for too many days in a row, I know I need to change something.” So if the sight of your coworkers or boss makes you ill, it’s probably time to jump ship.


Here’s the thing about jumping ship though; the origin means deserting one’s post. It meant to abandon the ship, not because it was on fire, but because you find out that the sailor’s life isn’t for you. We often think of quitting our jobs as abandoning our post and leaving our friends to sail off into the unknown, a person down. But we’re not at sea. Another person can fill your spot. This is about your pursuit of happiness. And if you’ve stopped growing, the relationship has run its course, or you’ve simply need to leave, then it’s critical that we make sure we know how to swim to shore.

Routes to Pivot – Hindered by what I knew was Possible

When I first started my pivot, I was so clueless as to my options for both types of jobs and ways to make it happen, that I found it difficult to make progress. I was hindered by my lack of exposure and, to the extent at which I can help, I want to make this a bit easier for anyone looking for their own pivot. I’ve met with enough teachers to see a pattern emerge of what works and what doesn’t work in pivoting their career. I tossed around each of these ideas for my own pivot three years ago, including the one that doesn’t work. And there is only one that doesn’t work. Let’s start there. 

Do you have any hopelessly single friends? Does every conversation with them turn into an emotional deep dive about the state of their love life? Is it emotionally draining to even keep up with the latest news? Do you wish there was a dating app for a smaller segment of people that arranged marriages so you can move on with the conversation? When I first realized I wanted to leave the classroom, I became that person. I cringe at the thought now of how many times my conversations with friends turned inward about myself and I grasped and clung to any possibility of regaining solid ground. It was emotionally draining. I felt like I had people analyzing my resume on my behalf the way people frantically deliberate their dating app profile picture. Which adjectives should I use to describe how awesome I am but still look really humble? And honestly, the job hunt feels a lot like dating. It’s filled with immediate hopes, rejections, navigations of conversations where you read into what people say. It’s exhausting. Getting into this desperate state where you just want to have something work is the only way to make it not work. The good news is that if you enter this state, it’s possible to escape it. The bad news, even if you do the other things right you can find yourself proverbially swiping right on any job with a salary and health insurance. 

The most important thing is for the pivot to move you forward. The routes I’ve seen work well are as follows: 

  1. The Grad School Pivot AKA if I don’t want to teach then I’ll go back to being a student for a new beginning
  2. The Bootcamp AKA I want to develop a concrete new skill to open doors
  3. The Network AKA I’m going to talk to enough people until someone helps me open a door
  4. The Movin’ on up to Central Office AKA I want to stay in education but I want to flex muscles outside of the classroom

I interviewed my friends who have done the aforementioned pivots in the hopes of helping others figure out what is the best route for them.

1. My friend Lucy did the grad school pivot. Lucy taught middle school social studies as part of Teach for America. 

What did you teach? Middle school social studies in Memphis, Tennessee. My undergraduate was in history.

How many years did you teach? 2 years for Teach for America. One of the problems was I didn’t feel like I was improving as a teacher as fast as I wanted to improve. I didn’t feel equipped. I was looking for something I felt like I could be better at. I got burnt out on charter schools and, looking back, I wish I had tried other types of schools but I was really excited about going into public policy.

What masters did you get? LBJ School -Master of Public Affairs

How long did it take? 2 years

What did it cost you? Americorp funded and instate tuition- I had a graduate research assistant appointment and teaching Assistant appointment so it was free. I’d recommend everyone find ways to make it affordable because typically there are.

What immediate doors did it open for you? The networking opportunities are amplified when you go to a professional school. The benefit isn’t the curriculum or what you learn, it’s about the network you develop.

Was it worth it? Would you do it again in order to pivot out of teaching? Grad school was definitely worth it for my route. There are other routes to where I want to be professionally. While in grad school I worked for the legislature and I got exposure to really interesting state agencies that I think I’d like to work for in the future. There are pockets of innovation within state organizations that are doing awesome work.

What was your job title for your first job post grad school? I was dead set on doing K12 policy. I wanted to work in state or district level. The first job I got was working in policy in higher ed and I completely fell in love with it. I had a misconception that equity issues were concentrated in K12 and learned that isn’t true. I found there were a ton of connections to my work as a teacher in the higher ed policy realm. I worked on metamajors and math pathways for community colleges to the four year.

Any advice for teachers who are considering the same?
You need to think about the investment you want to make. I didn’t gain skills in that degree and I wouldn’t recommend anyone go to grad school and take on debt. If you’re considering a program that costs a lot you should consider why. I wasn’t personally going to take on a lot of debt so that changed a lot of my outlook.

Female teacher perspective here- you often don’t know your value and worth. You’re doing  a really hard job for not much money so it’s also a mental pivot to know your actual worth and advocating for yourself and demanding it in your first job. You need to recalibrate your worth. It’s not obvious to others what you’ve done as a teacher but many don’t know how to articulate that. Be able to describe that to an employer or a grad school interviewer.

2. My friend Sean decided that becoming a project manager was closely related to his high school administrator duties and did a boot camp.

What did you teach? Middle School Social Studies then later was Dean

How many years did you teach? Seven!

What masters did you get? Master of Education, Secondary

What bootcamp did you do? Project Management (PM), UT Extended Campus

How long did it take? 2.5 months

How much did it cost you? $4,000

What immediate doors did it open for you? I firmly believe that the PM certification helped me get my current job. I don’t really know if it was for the content, though. The classes I manage are in the same building that I attended classes in. Familiarity was important to them. In addition, I had just finished an evening class while holding down a full time job, which most of the students in our bootcamp are doing. Familiarity with their situation was also important to them. Was PM important to them? I’m not really sure. I did find out after I got the job that there were about 13 other people vying for my position. In addition, LinkedIn sends me PM job opportunities about once a week. There are a lot out there.

Was it worth it? Would you do it again in order to pivot out of teaching? Absolutely.

What was the title of your first job post program? Student Success Manager

Any advice for teachers who are considering the same? You have skills that are valuable in the non-teaching workforce. Don’t feel trapped or discouraged by your current situation. Also, don’t feel guilty for wanting to leave teaching. YOU are not responsible for every student in your community, or the state of public education in America today. You have a life, perhaps a family, and your needs are important, too. Politicians and voters at large are responsible for turning a noble profession like teaching into an over-worked, micro managed, under funded, under compensated, insanely stressful and litigated mess that it is today. You’ve done the best you can with the shit sandwich they handed you. Go live your life.

3. The network is the approach that I took. Man is it exhausting. I’ll answer the same questions as my friends.

What did you teach? High school math

How many years did you teach? Seven

What was the network approach? I hit up anyone and everyone who could possibly help me find a job. I had countless email threads, phone calls, and coffee meet ups. I spread myself pretty thin over the summer months to find a company that would hire me but ultimately the job I got was connected through a friend of a friend. The tough aspect of this approach is that it feels like it’s dependent on who you know. If you don’t know anyone then you have to start the process of getting to know folks. 

How long did it take? 4 months

How much did it cost you? Free but I probably spent $50 on other people’s beverages.

What immediate doors did it open for you? I got a great sense of what my options were and the cultures I was looking for. It taught me how to job hunt which is a great life skill in general. 

Was it worth it? Would you do it again in order to pivot out of teaching? It worked for me but I can see why others would avoid it. Depending on your personality, this might be a nightmare. 

What was the title of your first job post program? Business Development Representative (entry level sales)

Any advice for teachers who are considering the same? Use LinkedIn and don’t be afraid to meet strangers. It’s human nature to help people and if someone doesn’t want to help you, they won’t both responding. Try to find former teachers that have already blazed the trail and can connect you to the right places. If the job you’re applying for uses the soft skills you have a teacher, you can network your way into the job. 

4. My friend Jenna comes from a family of educators and knew that’s where her heart belonged. After a few years in the classroom she saw the gross injustices that are passed onto our public education system by our legal and legislative bodies. Her pivot, law school. Three semesters in she realized that while the end goal of improving the system remained, she realized that for her, law school was them most unnatural way to do it. So she pivoted to main office to help create change at a broader scale. 

What did you teach? I taught mathematics: Algebra I and AP Statistics, then Dual Enrollment Statistics through UT.

How many years did you teach? I taught for about 8 years.

What degrees do you have? BA in Math

What central admin job did you get? Secondary Math Specialist

What immediate doors did it open for you? Depends on what you mean by doors. Although a Master’s degree was preferred, it was not required for my position. So although I was hired because of my experience, the jobs “above” me that I could potentially move into later (supervisor, director, etc.) were unavailable unless I decided to go back to school for my Master’s degree.

Was it worth it? Would you do it again in order to pivot out of teaching?
Yes. I had always wanted to be a teacher. In my classroom, I felt I had improved over the first several years of teaching, then I felt like I stopped growing. I worked as an instructional coach for a short while before becoming a math specialist for the district and as a specialist, I finally felt like I was growing again as a professional. Supporting teachers was a totally different ballgame.  Most teachers take a lot of ownership and pride over their teaching. So working to help them improve required a delicate balance of letting go, positive encouragement, and constructive criticism. One thing I felt I always struggled with as a teacher was planning/asking questions that allowed my students to engage in deeper learning. I was constantly working to ask questions that didn’t just tell them what the next step was. And while I did improve over my time as a teacher, I felt my ability to ask questions drastically improve incredibly rapidly as a specialist. Adults (and students) need broader and deeper questions that really make them think in order to grow. I had to up my questioning skills in this position.

In this role, I was also allowed/encouraged to attend professional development outside of my district. Hearing from other specialists or teachers always challenged my way of thinking and pushed me outside of my comfort zone. This was not encouraged as a classroom teacher in my district. It would take small miracles and/or outside funding to allow me to attend quality professional development outside my district. 

Then, when I would come back, I always challenged myself to deliver similar PD that I had received in a way that was effective for my teachers and authentic to my own style. I felt I grew professionally with every training/PD I delivered. 

Any advice for teachers who are considering the same?
Don’t be afraid to reach. I know many people who wouldn’t have considered applying for the specialist position without a Master’s degree. I was confident in my teaching abilities, math knowledge, and ability to learn and that is what got me the job. 

So where does that leave you? Some pivot routes may not be options but thanks to the internet, online masters degrees and bootcamps are always options. The routes for each individual will be different based on geography, opportunity, time limitations, and interests. Knowing what else you can do is half the battle. Knowing how to fit into this outside world is a big obstacle. I often sit with teachers who don’t know where to begin. The next step I’ll focus on is the down and dirty tasks of pivoting and the steps to ensure that every individual can answer the question “If not this, then what?” 

The Stigma of Teacher Pay: Coming to Terms with Naming Your Number

Money is a weird thing for me. I left the classroom in the fall of 2016 to work at a tech start-up. It’s been a long journey and I often feel scummy when dollars come up. I want to share this experience with others because I always felt limited by what I knew was possible. This isn’t a 1969 moon landing with all of America watching, but knowing what is possible will help everyone be the best version of themselves. So in this, I hope to provide a bit of my experience for any teacher who is struggling to figure out what to do next.

The first time I got a bi-monthly paycheck that was equivalent to my entire yearly teacher salary, I just stared at the computer screen and felt an overwhelming sense of pride. It was extremely difficult to pivot careers and to make this type of thing possible. My wife and I would often take walks with our dogs and talk about what we’d do when our careers “took off”. Mine had officially taken off. I had been out of the classroom two years and six months. The second time it happened, I was already planning about how to make it happen for a third. The scale changes very quickly.

The desire to get out of teaching almost always includes some financial motivation. Even a 10% increase from a teacher salary can be life changing, much less doubling or tripling that salary. Knowing your worth and leaning into this aspect of the transition out of teaching is mandatory and being naive can only cause damage.

When I first started to get curious about moving outside of the classroom I reached out to everyone I knew that could possibly know something I didn’t. This was a high number of people. I reached out to my college friend, Dane, who had become quite well connected in the tech start-up world. He was the first person I had ever heard of going to an “incubator” in California. At age 24 he moved from Texas to San Francisco and got a rent controlled apartment in The Mission and now flies back and forth between NYC and California as a VP at a SaaS (Software as a Service) tech company. His world was mind boggling and intimidating to me. I had imposter syndrome just asking him for help. At the time, I was making $45,000 as a teacher in one of the most expensive cities in America. The previous year, I became a homeowner. I got my property tax statement around the same time as I got my raise for the next school year. My home would cost me $960 more per year in taxes but my raise was $500 to get me to $45,500. I was effectively net negative $460. I drove Lyft and Uber for 6 months to make up for my extra expenses and I felt like I was wasting my time. All of a sudden, in that moment, I became a grouchy old man complaining about taxes. Ironically those property taxes fund the schools and thus pay the teachers so this scenario was quite painful. 

During one of our conversations he asked me how much I wanted to make. I had thought very hard about the number I needed to feel really great about a transition. I thought to myself what extra work I’d be doing without summers off and what that would equate to. I thought about my property taxes. I thought about how I wanted to get married and possibly start a family. All of these numbers swirled around my head and like a mathematical savant, I leaned back in my chair, crossed my arms, and confidently stated $60,000 as if I were negotiating a massive merger between two railroad companies. Dane paused. He then said, “You should aim higher.” I found myself sinking in my chair a little bit. I couldn’t tell if my goal salary was just based on lack of data points or if it was a reflection of what I viewed as my worth. Either way I realized that I had to come to terms with money in a way that was previously never an option. 

“You should aim higher.”

According to the Bureau of Labor Statistics, for 2018, the median annual wage for high school teachers was $60,320. The range for teachers is vast. Not only does it depend on years in seat, type of advanced degree, or subject area that causes these changes but the geographic location greatly inflates the median numbers. The lowest 10 percent earned less than $39,740, and the highest 10 percent earned more than $97,500. The median for Texas is $57,800. The median for New York is at the top of America’s list at $81,290 whereas Oklahoma, who popped up on the national news cycle with their teacher strike, came in at $41,280. What is even more critical to understand is where do these wages fall in line with the wages of the country. The National Association of Colleges and Employers (NACE) calculates that the preliminary average starting salary for graduates from the class of 2018 is about $50,004. There is an inherent disconnect when the median salary of a group of dedicated, hard working, well educated professionals with upwards of 20 years experience is not far off from the salaries of the students they taught just a few years prior. 

I recently had this same conversation with my friend, Jeremy. He was in the middle of an interview process and we met up over a drink to walk through his situation. I asked him the same question that Dane asked me. He said he did the math. As a teacher in a very demanding charter school, his salary was higher than average at near $53,000. He figured that he worked 10 months out of the year and if he took that rate and came up with a yearly salary to make it worth it, his ideal minimum number was $64,000. What he really hoped for was a salary of $70,000. The sales job he was applying for had a base salary of $42,000 and if he performed at quota, his yearly salary would be $65,000. And the job came with uncapped commissions which meant that if he worked smarter and harder, he could make even more money. Teachers are always trying to work smarter and harder. 

The day after my conversation with Jeremy I had another meeting with a current teacher. When I asked him this question he simple exhaled a breath of frustration and just said “more”. I encourage anyone looking to pivot careers to really examine how much they need, how much they want, and cross reference that number to the career options. No one wants to hire a desperate burnt out teacher. Know your number and make it happen. 

The idea that the only way to give back to the world is to also be poorly paid is false. Most teachers I meet with have a martyrdom complex that still personally comes knocking for me. These types of deep, emotional feelings often keep us locked in place. We often convince ourselves that our low pay makes sense. We get summers off. We get nice holiday breaks. Sometimes our work hours are shortened. But we know, the summers are shorter than the parents realize. Our holiday breaks are wonderful but if you can’t afford to travel then a staycation it is. The time perks are not a perk. It’s borderline mandatory to get that time away from the classroom to refresh yourself. Bottomline is, and this is obvious, but teachers are severely underpaid, under-appreciated, and misunderstood. However, this is about how you can transition into your future. Part of that is accepting how things will be different and shifting expectations to match a future reality. 

So when Dane told me to aim higher, I thought, “$70,000!” He kind of laughed at me again and said, “Shoot for $80K”. $80K. I thought, “Wow! That’s more money than I’ll ever need.” My first job offer was a pre-sales job that required me to book meetings for the sales team. My base salary was negotiated to be equal to my teacher salary and if I hit quota my total yearly salary would be $80,000. I didn’t know if it would be easy to hit quota but once I realized that the harder I worked the more I could get paid, I made sure that every month I was making more than I was as a teacher. At that time, my wife decided to pivot herself and go back to school full time. With the help of small loans and big grants to cover tuition, I was able to float the household needs because of my new job. Two years of this and my wife worked hard to became a college graduate and now has an amazing career of her own. This would not have been possible without our decision to pivot my career change. This is what makes a life trajectory different. People talk about the pay and as a consumerist society we think the pay increase will lead to the newest electronics or an upgrade in vehicle, but what we don’t talk about, and we should, is the amount of pride and accomplishment I felt that I could take 100% ownership of the household finances while my wife took two years to better her own life. Our life trajectory is different because I left the classroom.

I would always try to figure out the best path for my students and give them life advice that provided them with the optimum trajectory. It just so happened that for me to take my own advice, I’d have to metaphorically find a new classroom.

You’ve Been on Your Soapbox About the Importance of Teaching and Now You’re a Capitalist Pig: How to Come to Terms with this Change and How to Navigate Conversations with Friends and Family. 

When I announced to my classrooms that I was leaving for a career in software sales, a few of the students were really perplexed. It honestly did make me feel like I was choosing to abandon my kids. I didn’t know how they’d react. In one of my sections a girl said “ughhh why are you leaving?!” It was said in somewhat of a playful understanding tone, but a sad tone nonetheless. I didn’t know how to respond. Fortunately a boy in the back did it for me. 

“Mr. Frasier just needs to chase the cheddar!”

I had literally never heard someone say that phrase before but I immediately knew what he meant. He gave me an approving head nod that I found comforting. I didn’t know I needed my 17 year old class clown to tell me it was OK. I did. But in the moment I was able to somewhat break down why I wanted to leave and now 3 years later I’ve been able to synthesize a bit on the wording of why I went from a passion profession to one that is not associated with public good. This comes in handy often. 

I was just at a wedding for a family member. My cousin came up to me and said “Are you still teaching?” It’s been almost three years. This identity permanence is one of the hardest things about the transition out. I have developed a lot of talk tracks around these conversations. Here are the highlights. 

  1. On why I left the classroom– I spent years telling my students to reach for the stars. I told them I believed in them. And it was true. Anytime I had my students not realize their full potential a part of me was sad and I put even more energy behind getting the students where they should be. Even after their graduation, I would find myself in mentor roles. I wanted them to live their best life and find the limits of their capabilities. I realized that for me, my  professional and personal growth rate had slowed down in the classroom and I wanted to have the same hopes for myself as I do my students. The last sentence is now my answer on why people ask why I left. And it feels more true now than it did 3 years ago.

  2. So do you miss teaching? I get asked this all the time. I honestly never ask my friends if they miss their old job. It wouldn’t make sense. It’s a harmless question but I hate it. It encapsulates our views on teachers being monolithic entities, forever wiping down dry erase boards until we go to old folks homes for teachers where we talk about how good freshly printed tests smell. The answer to the original question changes. Sometimes I say yes. When I say yes, I have to clarify what I miss. In the classroom I felt totally in control. Every day’s lesson was up to me. That might not be every teaching situation but there are elements of every day where you are in charge. I feel more beholden to something else now and sometimes that’s stressful in a new way. Sometimes I do miss interacting with young people. I quickly became out of the loop of the younger generation. Like many millenials, I don’t have regular tv. I don’t see commercials. I don’t listen to radio. Every piece of content I consume is curated by algorithms to reflect back new things that already fit my preference. Students keep you young and knowledgeable. At one point it was so bad that when someone was talking about knowing how to floss I legit thought we were talking about dental hygiene. I miss being in the loop of stupid trends. Sometimes I miss feeling like I’m truly changing a life. But now my answer flows mostly like this: So it turns out the thing I loved the most about teaching wasn’t math or working with young people, it was the feeling of helping someone change for the better. Luckily, I still get that feeling a lot from my job. It turns out I can get that same feeling from helping adults as well.

  3. So how does it feel being a corporate sell out? This is a very personal section and I hope that the reader is patient as I wrestle the conflicting thoughts. I was never too far entrenched in leftist politics but I do own more than one book on anarchist philosophy and I hold a few radical thoughts on how to correct the wage gap between workers and their CEOs. Many of my journalings in college and early teaching days were focused on my rejection of societal expectations. While my engineering school classmates were daydreaming up what cars they would buy someday, I decided to not even bother with our engineering exit exam that would allow me to work in the industry. I chose a life of service and financial constraint in order to adhere to my value system. This has honestly been the hardest part of the conversations with friends and family. I know what the lives of my students look like when they don’t have food beyond what the schools provide to them and, therefore, the idea of people throwing $80K at a Tesla doesn’t sit well with me. What would happen if that $80K was put into a program that helps young folks get their foot into the community college and into a life that changes everything? Even when people say “But the person with the Tesla worked hard to get the money for that car and it’s their right to do whatever they want with it.” I have a hard time reconciling what I would do in that situation. So while I personally struggle on how to strike a balance between the selfless service of teaching and now earning more, I’m reaching to audit all the things I can do in my life now that are more meaningful because of my career change. It all boils down to one thing: family. Around the time I was planning on leaving the classroom I was also planning a wedding. My wife wanted to go back to college. I had a car with 150,000 miles on it. I own a home in an up and coming part of town but there have been two incidents of drunk drivers hitting parked cars within 100 yards of my house this month. There was a shooting 3 months ago. Kids aren’t found running freely around my streets. There are big life things that are different now that I’m a sell out but I also feel a sense of pride that I’m able to do things for my family. But I go back to response in section two. I’m not doing this 100% because of the pay. I’m doing this for personal and professional growth and it just happens to pay more. 

The most frustrating thing about this is that teaching is one of the only professions that struggles with this. If you’re leaving a non-profit, you may experience a bit of this struggle but people change jobs all the time. People leave companies to take promotions elsewhere. People work in industries that don’t contribute to any social good but the career allows them to provide for their family or provide them with time and energy to give back to the community. No one really questions these things for other professions. And, it’s really possible no one else is questioning these things for me. Maybe teachers are doing this to themselves. But if you decide to leave, these are things you will come across. Whether it is self inflicted or societally imparted, there will be fleeting moments of identity struggles.

The best thing we can do for ourselves is to create situations where we can maximize our own good, our family happiness, and our impact on the world. Sometimes you can do those things and your career is irrelevant, for once.

Are You Selling Out by Getting into Sales?

I’m going to tell you a true story about my first day in sales. 

My first day was on a Wednesday. As some of you might know, my career prior to sales was teaching high school math, and I left two weeks into the school year. This was not received well.  

The night before I started my new sales job, I was at Meet the Teacher Night at my school and I showed up to meet the parents and introduce my replacement. It was awkward. It was like breaking up with someone but still being around to say, “But I found you this new person!” I got home at 9 pm. I was too exhausted to be nervous for my first day of the new job. 

The next day, I started my new job at a tech company at 9 am for an initial HR onboarding day. I was told that I’d be meeting the sales team for a group lunch. I had the “new kid at school” feelings and was worried if I’d fit in. 

After we grabbed our lunches, we went into a conference room where I was immediately greeted by a bunch of intimidating type-A people. It was a chaotic whirlwind of handshakes and rapid fire questions. I was told that coffee was for closers. I was asked how much cocaine I did. I was asked if I was ready to hit the phones. Every other word was an expletive. I was told that if I was last place on the leaderboard I was fired. I was asked if I wanted to get rich. I hadn’t heard adults cuss in a professional setting before. The volume was such that if it were my classroom I would have gone into damage control. It was the absolute worst first impression I could have had. Less than 24 hours before, I was talking with parents about the importance of community in the math classroom and now I was living in Wolf of Wall Street

What I didn’t realize is that everyone was joking and is actually really nice. They were in rare form and decided to quote a lot of the famous movie Glengarry Glen Ross. My hiring manager was mortified. I hadn’t seen the movie. I was so perplexed by their vulgarity. 

About a year later, I watched the famous clip of Alec Baldwin’s 7 minute motivational speech and I realized everyone who greeted me on my first day was playing the stereotype of sales. They were more or less inducting me into the team. 

Over the next year I learned a lot about how modern sales isn’t slimy and why former teachers are great for this role. Here are some reasons why:

  1. Teachers know what is good for others and help them get there. In the movie Inception, they talk a lot about the difficulty of planting an idea in someone’s head. Teachers understand this: How do I get a student to realize their full potential and change someone for the better? Teachers recognize the issue. They diagnose. They do this by listening. By observing. By letting the person across the table talk and then being responsive. They practice radical empathy. Change is the hardest thing people can do and teachers help children or teenagers change, all the while being subject matter experts. This is exactly what sales is. Sales is helping people create their best future.

  2. People can do informed research on the internet before they buy. Amazon has done a lot for our ability to read reviews and get the best price. Even in car sales it’s easy to figure out the factory price and to see a dozen options for the same car before you even talk to a sales person. When people work with a sales person, it’s totally different than the pressure to sign a contract and the deceit we associate with “slimy sales.” When people work with modern sales folks, they want to collaborate. They want to be helped through the change process. If you are working with the right prospect, they want you to help them sell internally. This is totally different than what I imagined sales would be like. People want to buy from someone who teaches them something new.
  3. Sales is the continuous pursuit of progress in the face of constant disappointment. When teachers work with their students, they face more setbacks than forward movement. Years later, teachers may see the fruits of their labor with students—that’s the same with prospects. The ability to recognize the micro-progress in the face of a surface-level defeat is something teachers can do. Ever have a student go from failing miserably failing to only-kind-of failing? Do you know that feeling of pride in progress for the student? Ever work with a student who makes major progress academically but still struggles socially? Teachers can see the good that happens with hard work and they don’t need to knock it out of the park every single time. Most importantly, teachers are trained to treat each situation with fresh eyes and continue to work hard with every student. That’s the same with prospects.

  4. Teachers see the forest through the trees. They can plan long term and start with the end objective in mind and work themselves back in time to what needs to get done today. The ability to lesson plan in teaching translates so well to sales. Teachers know what should be achieved and they’re able to make it happen because you see the steps to get there. They are also patient because they’re used to many of their student learning objectives taking up to 6 months to achieve. This is your sales cycle. Good sales people help solve little problems until a solution is put into place that allows the main solution to be adopted. Good sales people are trusted advisors. 

The above reasons are why teachers would be good at sales but it’s also why teachers shouldn’t feel slimy by going into it. I remember saying during my first year of teaching public school that I would never teach at a private school because I didn’t want to sell out those who really needed me. A lot of the feelings I had about the private school world were wrong. I was just as wrong about sales.

How to Get Out of Teaching and into Sales

It’s June. Graduation excitement is in the air. The students are excited for their summer and the teachers are asking themselves how to best utilize the few short weeks of freedom that is often over exaggerated by the masses. And for any teacher that has a renewal contract in hand, they are asking themselves, “If not this, then what?”.

Through a series of unrelated events, two friends put me in touch with two of their KIPP teacher friends who are humoring the idea of leaving. Both are in pushing 30 years old. Both have respectable years under their belt. And both feel the same weight of the question; If not this, then what?

A lot people ask me, “Patrick, how did you get out of teaching and into enterprise software sales?” Actually, no one has ever asked me that. But these two KIPP teachers were actually interested in some kind of sales job and did pick my brain on how to get into sales. This is my advice.

First let’s get some things straight. There is a vast spectrum of what sales even is. You have door to door (D2D), business to customer (B2C) and business to business (B2B).

  1. Door to Door is your cable provider or your solar panels. From what I’ve learned from peers who do this type of sales, it’s a volume game that rewards a certain style and personality and the number of doors that you’re willing to knock on. I have a lot of respect for these people because it terrifies me.
  2. Business to Customer is cars, electronics, etc. It’s when a customer comes to the seller and is shopping around. You have to convince one person that the product is for them and they decide on their own if it’s worth it.
  3. Business to business is when one business’ offerings are sold to another business. These sales are complicated. They’re often multiyear contracts. It’s based on some sort of proven ROI or there is a proposal evaluation process. This is where multimillion dollar contracts are signed and a lot of people have to buy in. This is the lay of the sales land.

I didn’t plan on going into sales but after a few years I can easily see why I found a route in this profession. Teachers naturally sell. They sell ideas. They sell solutions to problems. They sell inspiration. They sell motivation. Selling means getting someone to buy in. In the modern business to business world, it takes 6.8 people to say “yes” to the decision before a purchase. How often does a teacher have to come up with a value proposition to sell an idea that causes buy in from a group of people? EVERY 10 MINUTES. If you’re a current teacher, let’s think about a specific situation we’re in often. A student/parent/department chair/principal has a problem. They come to you and you take a seat in your classroom. For the sake of this example let’s pretend it’s a parent. You start the conversation by saying “Ok. It seems like we have some things to discuss. What’s on your mind?” The parent across from you begins to speak about the struggles of their student. They say things like “My student used to like reading and now their grades are dropping.” You say “Yes I imagine that’s very frustrating. Tell me more about their situation so I can better understand.” And before long you are learning about the student’s lack of sleep, how they recently got their heart broken for the first time, how the parent is working more and the student is responding poorly, how the parents are recently divorced, or whatever combination of events is the “why behind the why” the student is struggling. Now that you know the “why behind the why” you can actually sell the parent the solution that actually makes sense. Good sales people find the fit for the customer and then get the customer to convince themselves of the route they should take. I’ll talk more about these types of things in a follow up post. Now that we know teachers have a natural fit in sales, let’s talk about there to start.  

Let’s first get an understanding of the typical hierarchy of a sales team. Since I come the B2B software sales world, this advice will be focused on that. At the beginning we have Business/Sales Development Reps. They’re called BDRs or SDRs depending on the convention of the company. These folks are the ones who generate leads for the sales team. Some companies outsource this and the entire jobs is to read from a script and call hundreds of people a day. There are quotas on the number of calls you make and the number of meetings you set. Personally, that sounds really awful to me. The TV show The Office actually provides a great framework for this. If you’ve seen the show all the way through you may remember when Michael Scott has to take a second evening job at a call center. It seemed awful. This is outsourced BDR. What is MUCH MUCH BETTER is an inhouse BDR team. This is where you are setting meetings for your own company and your own teammates. You’re trained internally and have a career path with the company. Even if you don’t stay in sales you’ll be able to pivot once you’re in. This was my first job out of teaching. Typically the compensation is based on a split model of a base salary plus commission. My first BDR job had a base that was the same as my teacher pay and I had the opportunity to double the salary if I hit quota each month. I didn’t know how realistic hitting quota would be but I hit it more often that not. This is a pretty high paying BDR job and I got a bit lucky for my first go round. Often times you’ll see roles where the base is around $30k and the OTE (on target earnings) is typically double the base so you have the opportunity to make $60k if you become a high performer. A mandatory question if you’re interviewing for this role is to ask how many people hit quota. The company will almost always say a majority of people and they can lie to your face. I’d recommend asking someone on the team itself to get a realistic picture. A second important question is if the quota is capped. If it is, don’t work there.

The roles after BDR in a traditional structure would be mid-market sales or inside sales (ISR). In The Office example this is Jim and Dwight. They sit at their desk and make sure they have calls with prospective clients and they get the paperwork done. You typically don’t travel and you’re dealing with mid sized companies or middle tier sized contracts. Every company is different. In this role your commission is based on what you sell compared to the BDR role where your commission is simply setting up a meeting.

The next step is account executive or outside sales. Every company is different so it’s impossible to look at a title and know which type level it is but this is when you hold big meetings, travel, have big clients, and sign big contracts. These are generally the most lucrative roles. In the software world, these people can have a base salary in the low six-figures with and OTE ranging from $200k to $300k. Obviously these sales jobs are found in major cities but often can be remote since companies want their sales reps to be living in the territory where they sell. That means you can land a job where you work from home and make six figures but there is a component of travel. For some people this means a flight and a night in a hotel every week. My job has peaks where I  travel every week for a month and I spend 8 nights in a hotel. You get used to it but it’s not my favorite. These types of roles require major discipline in time management. Do you think a teacher would have a hard time managing themselves? I laugh at the thought.

So how do you get into sales? For this post I’m going to assume most teachers would have to start in the BDR role so I’m going to focus on this for my tips. The first thing I would do as someone that is wanting to get into entry level sales is read two books: The Lost Art of Closing and Rejection Proof. These two books will get you in the right mindset of the job and demonstrate what you need to know for the interviews. So what happens in these interviews? First, there is almost always an HR call where they screen the candidates. They want to know how you sound on the phone and how serious you are. This is why reading the books is critical. You can’t look like you’re testing the waters with your job application. Be a student of sales so they know you’re legit. There is an assumption in the market that lots of teachers humor the idea of quitting every year but they don’t actually do the proper things to stand out. I asked my old boss who hires people monthly about what teachers (and anyone else for that matter) should be doing to get the job.

  • What are the first things you look for in a first time BDR applicant? I’m looking for someone with curiosity, the ability to deal with a bit of ambiguity, detail oriented, excited about life and the potential to grow. I ask myself, “Can they pick themselves up quickly after being disappointed. Are they willing to try things that might make them a little uncomfortable?”
  • What could teachers do to help themselves stand out in their resume? What can do they do better on the first screening call? The candidate should highlight the times they had to sell an idea or use their creativity to transform something. I would also make sure they have a really good cover letter explaining why they want to move out if teaching and into sales.
  • What are some major mistakes you see people make who are trying to break into sales? There are sales muscles that you should flex the interview process allows for those to naturally be demonstrated. So often people don’t do sales like things during the process like following up after an interview, asking good open ended questions in the interview, and closing the deal.

Once you get past the initial interview, there is often an assignment associated with the process. You’ll be asked to write a mock email and leave a voicemail. They may even go so far as to schedule a 5 minute call with you to see how you handle yourself on the phone. The assignment portion is where they test your basic skills but it’s also testing one important asset of a candidate; how good are you at research?

Here is an example of the email my KIPP friend sent as part of his interview process:

Hi Ms. Jones-

I’m reaching out from XYZ company, a restaurant management software company, to set up a time for a call.

I had the pleasure of stopping by one of Abuelo’s locations in Austin last week and noticed there was some confusion around the availability and price of some menu items. I’ve seen restaurants at similar growth stages struggle to accurately update inventory, causing challenges with tracking available items and forecasting food costs. Fortunately, many restaurants have leveraged our software to streamline their inventory and vendor management systems.

Since you oversee inventory and operations, I’d like to grab 15 minutes of your time to discuss streamlining your systems, and if anything, I can give you a better idea of how to minimize losses and keep those tables turning.

Thanks so much for your time (and that tasty Durango Burrito),

Patrick Frasier
XYZ company

Another part of the assignment is leaving a voicemail. I give the same advice to every BDR on how to speak to executive assistants or how to leave a message. The key comes from the book The Lost Art of Closing in the concept of a value trade. The other important aspect is to call as if you’re equally important to the other person on the phone and have the tone of voice you’d have if you were setting up your own doctor’s appointment. Most of the time it goes like this.

“Hi. My name is Patrick and I’m trying to get a hold of Melissa. Is she available by chance or does she prefer to set phone calls via appointment?”

“Hi Patrick. She’s not available but what is the purpose of the call?”

“Ah ok. I work with similar company/industry/positions to help them with X problem and I’ve actually never met Melissa. I was hoping to set up a call to share what the strategies other people are deploying. It should only take about 30 minutes and it will teach her some new things. Do you control her calendar?”


This last question is important because it tells you who is in control. You’ll get various responses like:

“Yes. Send me an email with the purpose of the call and I will review it with Melissa and get back to you.”


“No I don’t. Your best bet is to just send Melissa an email.” or

“Yes. Melissa is free next Thursday in the afternoon”

For the purposes of a mock call- you’re most likely going to leave a voicemail and it should sound similar to the above script.

“Hi. My name is Patrick and I work with XYZ and I’m calling to set up an appointment with Melissa. I work with X company to help them with Y problem and I’d like to discuss that with Melissa. At the very least, she’ll get educated on some recent advancements used by others. I can be reached at ###-####. I’m looking to book a phone call sometime the last week of May.”

Now record yourself saying this script. Listen to it. If you’d hang up on yourself because you sound like a dumb sales person then try it again. That’s why I say to sound like you’re making a doctor’s appointment. Booking a doctor’s appointment is business as usual and your voice should reflect that. People are trying to determine if they’ll open the door for you and if you sound like someone that normally enters their home, the door will open.

Now hopefully you’ve gotten past the first couple of rounds of interviews. If you get past the assignment round then it’s basically about personality fit. I think most teachers don’t have to worry about this part. Teachers navigate awkward conversations and can be responsive to the dynamics of a room. More importantly, teachers are light on their feet. In my final interview for my first sales job, the vice president of sales did a one on one interview with me. About 15 minutes in he says “Ok. I’m going to be someone on the phone and you’re calling me. Ring ring. Hello.” I damn near threw up. But what do you do when a situation breaks out in the classroom? What do you do when you get an unexpected hard question? You spring into action and don’t even think about it. The VP wasn’t even testing my ability to properly answer the questions he threw at me. He just wanted to see if I could keep my cool. I only remember one smart thing I said in that mock call. When asked a question I didn’t know the answer to I said “That’s the crux of exactly what I want to set a meeting about. I can put you in touch with our subject matter expert on that.” Really I was deflecting but it’s the type of deflection that then puts the actual experts in the room together.

Another question I get asked often is what questions people should ask in an interview. One of my bosses always told me that the best questions to ask were the ones you didn’t know the answer to. You’re talking a company you barely know. Find out more. Who are their competitors? What’s the market like? What’s the hardest part of the job? How do they treat professional growth and development? What’s their philosophy on employee reviews? These are great things to discuss.

So now you’ve finished with all the interviews and you have a job offer. Here are some things to be careful about with offers.

  1. Get a base salary that is reasonable for you. Even if you make less for a month or two, know what the upside is after you get your groove.
  2. Make sure people actually hit quota within the company. can help you with this investigation.
  3. Do they have call quotas? What is it? Is it reasonable?

My advice at this point is that the first job out of teaching is a launching pad to your future. It in no way represents what you’ll be doing 2 years from now. Teachers can have a hard time with this. After your first year of teaching you get an idea of what life could look like 20 school years later. That’s not how the rest of the world works. Take a job that provides you with opportunity and people to learn from. And if six months from now it isn’t working out, you can pivot again. The second time will be easier. You’ve already opened the doors.

Why We Should Re-examine Our Approach to First Generation College Students

I hopelessly subscribe to Audible. I let my monthly allotted credits store up without listening to any new audiobooks, then I do things like buy 100 hours of books about the Civil War and think of how cool I will be at dinner parties when I say something like, “So, your story just reminded me of something that happened between Lincoln and General Grant.” When other people do those things, I hate them—but only because I want to be them. I digress.

A few months ago, I had extra Audible credits lying around. Amazon’s algorithm recommended a book called Education: A Memoir by Tara Westover. I downloaded it based on the title alone: I like education and memoirs. I didn’t realize how well it would fit into my thoughts on access, privilege, and how critical the role of education is in changing lives.

To be clear: there are some basic thematic spoilers below, but I encourage anyone interested in reading the book to go ahead and read it anyway. You will be surprised at how strikingly elegant Westover’s reflections are, and the reading experience is totally worthwhile.

Educated: A Memoir is about the path of a young woman who escapes her doomsday-prepping, government-fearing, anti-everything, traditional Mormon family in Idaho. Westover’s father was so paranoid of the government that she and her six siblings never stepped foot in a school—that is, until Westover was 16. I thought the book was going to be about fundamentalist religious groups but I was very wrong.

The book isn’t really about Westover’s family being Mormon. Educated: A Memoir is about escaping a troubled family and finding freedom in education. For her entire life, Westover was only taught to read and do math up to a fifth-grade level under the guise of “homeschooling.” At age 16, Westover decided to take education into her own hands. The point where the book took a huge turn for me (in the sense that I found myself continuing to listen to it while ironing pants because I couldn’t get enough) was when Westover decided she wanted to go to college. What unfolded from there was the type of sociological case study that happens when scientists find a new group of people who have never had encounters with the modern world. It was like I found a feral child and got to sift out what part of her experience with education was nature and what part was nurture. Hearing Westover’s story gave me a remarkably fresh-eyed perspective on what education can do for a person.

Here are some of my ideas:

1. What happens when self-teaching reaches its limit?

Westover self-taught the best she could in preparation for the ACT. Despite not having a high school degree or GED, she could automatically be accepted to BYU if she got a minimum ACT score of 28. It is impossible for me to imagine the process required to get to that level on your own. But, to be fair, she doesn’t fully get there on her own.

At some point, math (particularly trigonometry) prevented Westover from entirely self-teaching her own way to an ACT score of 28. Extra tutoring was required to reach that basic threshold, and that tutoring required her to drive for hours to her older brother who previously left their family and blazed his own education trail to BYU. Westover’s resilience conjured up so many questions in my head. If someone with only basic arithmetic skills can teach themselves math skills up to the point of trigonometry, what’s the role of a teacher in a traditional educational path?

Flipped classrooms are aiming to change the traditional dynamic of teacher and student. Flipped classrooms are a style of classroom where the students watch online lectures at home to learn the material, and in the classroom, the students work on what would traditionally be “homework” but with in-person teacher guidance. If some people can learn so much on their own, why do we expect and need teachers to be so heavy-handed in the classroom? Critically, the pedagogy to teach this way is predicated on the belief that students have the growth mindset to accomplish this—which can be considered problematic in its own ways. While flipped classrooms aren’t the only solution to this conundrum, they are certainly addressing the need for students to receive extra help with their personal blind spots.

Westover had only ever seen self-made people tackle their problems, so that’s what she did. Despite her family’s aversion to education, they never shied away from solving problems. One of the things I love about the book is that Westover doesn’t have a “bootstrapper” mentality. She’s not afraid to admit when she was fortunate. So while reading about her ability to overcome challenges, all I can think about is the fact that “learned helplessness” was never part of her childhood. What are we doing for our students who have more access to education than Westover, but who lack the guidance to embrace growth? I think the most important thing we can do for young people with lack of exposure to problem solving is to give them problems to solve in a guided environment. This is why programs like Girls Who Code, Latinitas, or Breakthrough Central Texas (my two favorite Austin non-profits) are so impactful—and why flipped classrooms are being examined as solutions. Once the habit of self-teaching is created, then the role of teachers can be optimized.

2. What the hell is a Blue Book?

In Education: A Memoir, Westover vividly describes the first time she took a college test. She paints a picture of the class opening their Blue Books in synchronized harmony—almost as if she had missed the previous night’s dress rehearsal. Until that moment, she had never even heard of a Blue Book. The only test she had ever taken was the ACT and she had no concept of what it meant to study, write essays, or read a textbook in the context of a college class.

So much of educational nomenclature and practice is a cultural norm that only makes sense to the exposed. It’s easy to see how the public majority would easily forgive Westover for not being prepared in that situation, or even be sympathetic to her. After all, how was she to know what a Blue Book is? Westover was raised in a backwoods, mountaintop junkyard family (literally). Is it as easy to forgive other disadvantaged, low-income students who do have a traditional educational background but have similarly little exposure to our educational norms due to a lack of support?

One of the best ways I’ve seen this combated with are first-year student success courses at colleges and universities. These courses are most commonly utilized at community colleges, but even elite universities like Washington University in St. Louis have a Center for First Year Experience (FYE). Schools like Wash U have seen their number of Pell recipients double in the past few years, which means they need to reevaluate their assumptions about their students. First year student success courses/FYE create a safe space to say, “Where the hell am I? What’s a syllabus? There is a writing center? What’s that for? What’s the difference between an advisor and a counselor?” If you don’t have the support network at home, your college has an obligation to provide it for you. But the best way to solve this is to start it young and that’s what makes the aforementioned Breakthrough and Latinitas programs so critically necessary.

3. What happens when our education creates a wedge in our families?

This phenomenon is a hard one to address. There is enough research (thanks Dr. Serrata) out there to say that first generation college students (FGCS) experience college differently, straddle two worlds (family versus college/university), and their student success rates are negatively impacted as a result. When you throw in the intersectionality and plurality associated with FGCS, such as race, gender, and socioeconomics, it’s easy to see that it’s a dissertation-worthy topic. Westover’s family situation creates an extreme case study in which we cannot ignore the impact of a child becoming more traditionally educated than their parents. Add female into the dynamic and watch some old-fashioned fathers’ heads explode. What’s fascinating about Westover’s family situation is that she is the youngest of 7 siblings and two of her brothers also have PhDs. How is it that in a family as tumultuous as hers, the three who “got away” ran towards PhDs? That can’t be a coincidence.

When we look at extreme cases, it’s easy to find patterns or draw conclusions on how something was possible. Similar journeys to Westover’s can easily be misconstrued by a reader as a logical, linear path to escape families, religions, or other potentially oppressive structures. When I’m reviewing scholarship applications for the Terry Foundation, I write “FGCS” on the margins because that explains a lot to me. As we begin to mandate college in our culture, we have to realize that there is no way around this problem. Someone has to be FGCS before we can get to SGCS. When admitting, teaching, mentoring, or coaching these students, we can’t ignore their pasts.