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?”