I Quit My Dream Job Because There’s Sadly No Such Thing

One of the benefits of financial independence is that you can try out different occupations that pay very little or nothing. You can even try to get a dream job. I've always wanted to be a grade school teacher, but I realized after doing some research you can't just become a middle school teacher here in San Francisco. Even being a substitute teacher requires many months of training, exams, and screening.

When a friend told me of an assistant tennis coach position at his son's high school in 2017, I jumped at the opportunity. In my mind, after five years of unemployment, this was a dream job because it combined teaching with my favorite sport.

Further, the job gave me an opportunity to understand the private school system. I want to learn in case my son doesn't win the SF public school lottery, see what it's like to interact with teenagers so I can be better prepared in 12 years, develop relationships with new people, exercise, and be a part of the education community.

There's a lot of debate about private versus public schools. And I wanted to see if private is really worth it or not.

Dream Job: Season 1, February through mid-May 2017

The first season of coaching was thrilling because everything was new. It felt like a dream job. I couldn't believe I was chosen for this position and felt grateful for the opportunity. I have the mindset that every job I get is like winning the lottery.

Despite having to shuttle students back and forth between school and the practice courts as well as matches, I was digging assimilating back into society. It had been two years since I last did some consulting for a couple financial technology companies.

Our team finished with the best record in school history, but we lost in the conference tournament finals to a school 3X our size. It was a bittersweet ending, but one that we were proud of.

Towards the end of the 3-month season, I was glad to be done with coaching because it required way more work than I had expected. My expectation of just showing up to practice and matches to coach was not the reality.

Dream Job: Season 2, February through mid-May 2018

I quit my dream job because there's sadly no such thing

By the time it was necessary to make a decision whether to coach again in 2018, I had finally recovered from the initial shock of being a new dad.

Those first six months were brutal, but it progressively got better with each month that went by.

Not returning for a second season would have felt like a waste. We had come so close to winning it all. My CPR training certification and coaching credentials were good for two years before I had to take an update exam. Further, I had already gone through the thorough background check process.

With unfinished business, I decided to give high school coaching one more go.

During the second season, nothing was new or exciting anymore. The dream job feeling was gone. The constant shuttling back and forth began to wear. Some matches were an hour away, which meant that on two occasions I wasn't able to get back home before my son went to bed. I felt terrible each time.

It seemed wrong to spend time with other kids instead of my boy given he was still so young.

In addition, I've discovered working with teenagers can be difficult. By the time you're a senior in high school, it's easy to just check out and not listen to your elders. I get it, but it still bums me out when there is a lack of respect. There was also a fight I had to separate one time on the practice courts.

Given my day usually starts at 6am, I was constantly coming home exhausted. Practice was between 3:30pm – 5:30pm, but I'd have to leave by 3pm and I'd often come back around 6:15pm.

In addition to being a dad and working on Financial Samurai, I'm also in charge of managing our wealth, which itself could be a full time job.

Despite the long, full days, I kept telling myself to hang in there. If we won the conference title, gutting it out would be worth it and I'd leave happy.

After several gut-wrenching 4-3 victories in the playoffs, we ended up battling our way to the conference final where we faced our old foe and last year's conference champion. But this time, we took them down with another 4-3 win!

Champions at last! Unprecedented! And funny enough, I finally got myself a medal.

Time To Leave On Top

Won a metal, nystagmus wristband

Now that we've done what has never been done before, it's time for me to quit.

Even though the season is only 3 months long, it feels uncomfortable to spend time with other kids over my own.

Over the two seasons, I developed some fantastic relationships with important members of the community. To be able to have a great relationship with the head coach, who also happens to be the athletic director at a terrific school, is a wonderful asset.

He's already told me he'd write me a glowing letter of recommendation to become a coach at one of the schools in Honolulu if we go. This alone, makes the grind worth it.

Winning the conference title was definitely one of the proudest moments in his career as the head coach and AD. As the assistant coach, I felt quite proud too.

I further developed good relationships with around eight great parents. They regularly came out to the matches to cheer their sons on. It was great. Surely if I ever need help with anything they have expertise in, they'd happily agree. After all, I helped their sons achieve something special.

No Such Thing As A Dream Job

Notwithstanding only getting paid $3,500 per season, I felt a tremendous sense of responsibility to do anything and everything for my coaching job. My work ethic has always been to try and provide more value than what was being paid. This way, I figured I'd always be employed or employable during difficult times.

The reality is that I would have preferred not to have been paid at all. After taxes, I didn't even realize I was getting paid in the beginning. I had to question what these random deposits were at random times.

Without a paycheck, I wouldn't have felt as obligated. It's that heavy feeling of obligation that took away from the freedom I'd so readily grown accustomed to since 2012.

A Dream Job Can't Exist Without Freedom

There is no dream job because you've always got to answer to someone, no matter how nice they are. And when you have to answer to someone, you've got to alter your behavior.

After being free for so many years, it felt weird not being completely myself during the season. As a coach, I must act seriously and professionally. And that's frankly foreign to my personality. I'm often times just an easy-go-lucky type of guy.

Having a dream job reminded me how much we have to change ourselves in order to fit in and grow in a work environment.

Hence, I came up with a best solution for next tennis season. And that is for me to volunteer for 2-3 days a week if they'll have me. After all, we have the possibility of creating a high school tennis dynasty!

In conclusion, the closest thing that comes to a dream job is working for yourself. Financial Samurai is absolutely a blast to run. There is definitely pressure to keep up the writing schedule. However, it's a self imposed pressure. Having nobody to answer to is priceless.

Recommendation If You Want To Quit

I recommend everybody negotiate a severance if you want to leave a job you no longer enjoy. If you negotiate a severance like I did back in 2012, you can not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training.

When you get laid off, you can also be eligible for unemployment benefits. Having a financial runway is huge during your transition period.

Conversely, if you quit your job you get nothing. Check out, How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye, on how to negotiate a severance.

I first published the book in 2012 and have recently expanded it to over 200 pages with new resources, strategies, and additional case studies thanks to tremendous reader feedback.

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42 thoughts on “I Quit My Dream Job Because There’s Sadly No Such Thing”

  1. FinallyAdulting1

    I have just been offered a new position at work and this article was right on time with helping me make my decision, I’m going to turn it down.

    The management is not ideal and even though a year ago I would have been grateful for the opportunity I really have to start thinking about whats best for my mental health as well as my financial journey.

    If I don’t respect my management then is it really a dream job?

    I have a general question, anyone feel free to respond. Is the position ever worth it even if the management and/or organization threatens your morale? Whats the “mature” way to handle these situations or am I just being a millennial who wants my cake and eat it too?

  2. “In conclusion, the closest thing that comes to a dream job is working for yourself”

    The “working for someone else” dream job is BS. I worked for someone else for 20 years, then for myself for 9 years. Working for yourself is amazing. My business has been winding down, so I went back to work for Corporate America for the last year or so. My attitude is still the same as when I was working for myself and I know it shows. It is very hard to fake the “team Player” attitude now.

  3. The idea of a dream job is very much illusional. You have come up with a great subject. Sometimes it is not easy to find a dream job that also pays well. I always look forward to reading something inspirational from your posts. Great post again.

  4. Sam–You do such a great job with your blog and podcast. I’ve been a reader for several years and listen now to your podcasts, sometimes even when I’ve read the same blog because you add a few extra comments! I am always impressed with your topics, research and clarity of writing and speaking.

    I teach Personal Finance to undergrads at a well-known eastern university (will have about 220 students in 2018) and online at another well-known northeastern university to MBA students (about 100 students in 2018) and am trying to find a way to incorporate your work in my course. Ideas?

    Overlap that helps me enjoy your work–I lived in Virginia for six years, know W&M, attended UVa, started playing tennis when I was young, worked on Wall Street in Corp Finance (sounds like you did Capital Markets and avoided NYC), read about, teach and enjoy personal finance.

    Keep the great work coming!

    1. That’s cool you were teaching personal finance! I’d be interested in helping out or bring some suggestions. Feel free to shoot me an email.

      I worked in New York City in the international equities department at GS from 1999 to 2001.

      Thanks for listening to the podcast! I do try to add a little bit extra here and there.

  5. Great post. I don’t think there’s something as a *dream job*, but maybe something more like a *dream day*. What would you do with your time if you had complete freedom? It’s what you’ve been exploring with early retirement, and, I assume, you’d spend your time writing and teaching, like you do with this blog. My dream day involves exercise, thinking, working, creating — all the things I do on a daily basis. The *job* requires some tasks that are, well, less than ideal. But overall, it’s dream day after dream day, as best we can.

    Congrats on winning!

  6. Rini Sherony

    Dear Sam,

    I love reading your posts and used lot of your advice. I have one question. I recently became an empty nester, my only daughter moved to college and suddenly I feel like having a lot of time. Rather than brooding over my daughter which I have been doing the past week, I would like to do something meaningful, I am interested in creating a blog of my own (non financial). Can you please provide me with some info on how to easily create one, what platform to use etc.? I am an electrical engineer by profession and not a coder, so I need a non coding platform.



  7. Those who can’t work, teach. Those who can’t teach? You’re in trouble! Haha…

    I thought the salary would be over 10k for sure, That is alot of work for almost no money

    Maybe you would be better off doing private tutoring, including adults? Prob $50-100 an hour…

  8. Still working

    I think it is called a dream job because it is still a job. Once it is a gift to others everything changes.

    You have figured out how to not need a job. That’s great you found a solution to keep moving forward.

  9. I think your experience coaching tennis and being successful at it my winning the championship shows that you have plenty to offer. You provided useful tips to the tennis players to help them propel to success.
    Maybe when you’re son gets older and has an interest in playing tennis, you can definitely coach him to play at a high level. That’s one of many things you got out of coaching HS boys tennis, to have the confidence to teach you son(if he wants) and to do it well.

    1. I definitely wanted to learn HOW to coach better and how to interact better w/ teenagers in order to be better prepared when it comes time to coach/interact with my son.

      I learned a lot for sure. So much about coaching is about knowing WHEN to push, and when to keep quiet.

  10. “the closest thing to a dream job is working for yourself”

    As a 47 year old who started my business at age 25 I cannot agree more. I’ll take the stress of self-employment any day over the stress of having a boss, and I urge anyone I know to somehow incorporate their skills into some sort of viable business model.

    Kudos to you for your volunteer work. We need more people like you in this world!

  11. Of course there are dream jobs, within the universe of what that can mean. In my case I have consulted part time for three years since leaving my 9 to 5 and since I do not need the money why else would I do it if it did not feel like it was a good use of my time, if I did not enjoy it? As a tennis player would I have ever thought coaching young teens for $3,500 a season would be a dream job? I can’t even type that without suppressing a hysterical giggle. Only someone who never raised a teenager could be that….naive. We built an entire second story on our house when our three got to their teen years to minimize any human contact with them. Now they are great doctors and engineers and educators but they were alien creatures for awhile there and the jury was out as to whether the same two people that brought them into this world might just have to take them out prematurely. I’m really going to enjoy this blog in a few years Sam!

    1. Ah, naivete is conquered through purposeful experience. I could sit on my hands until my son turns 13 to then try and figure out the teenage years. Or, I could inject myself in for two years as a HS tennis coach, understand what makes them tick, chronicle my journey so I don’t forget, and learn how to best interact with them.

      I did ingest some bad medicine with two or three players, and I think it’s to be expected.

      I will be looking to buy a mega mansion when my son becomes a teenager too! You see? How would I have any confidence in deciding on our next house without learning that you built a second story to be away from them?

      PS: I’ve been learning about being a mentor to 9-11 year olds due to my foster kid mentorship program.

  12. Kudos on reaching your goal and subsequently going out on top. Most would have thrown in the towel after that first season when they saw the sacrifices they made at the expense of other, more important areas of their lives. But sticking with it at least added to your self-esteem of knowing your involvement had a direct impact in those kids’ lives. Receiving that validation will always feel good.

    When you’ve grown accustomed to flexibility, taking on an obligation often feels like a weight around your neck. It would have been very easy to convince yourself that your time would be better spent elsewhere.

    However, the decision you made to assist was not purely selfish by making your hobby into a dream job. You wisely recognized that this position could serve as an in-roads for your son to receive a private school education in the unlucky event he doesn’t land a spot at a top-public school. So, by sacrificing those two nights with your son as an infant, you may have helped him in the long-run while also enjoying your coaching experience.

    Your decision to continue as a volunteer is a shrewd continuation of that social networking and building a safety net for your son. Talk about a win-win.

    1. Hope so!

      It’s fun to try new things all the time. And, it’s fun to actually achieve a goal you set out for.

      There is probably no amount of reasonable money I could get paid to coach to make me feel less stressed or obligated and to want to work FT. It’s a weird combo.

  13. Volunteering for favors or getting into a waiting list in the education/religious arena is a whole different ball game. It requires a lot of consistent and recent contribution and complete buy in to the culture and values of the instiution. Sometimes I think it can get a bit cultish but relatives and coworkers continue with their thankless hours to further their child’s futures in the preferred network.
    Someone else will come along after u for same reasons and there will be recency bias. Not just a one time thing. One word: competitive. As it is for profit.

    1. Tell me more about this world. I have no idea.

      All I’m doing is focusing on tennis coaching and building natural relationships with parents who decide to come out and support there kids. Some never or hardly ever do.

      I think I’m going to be the crazy dad who comes out to everything my boy does, whether he wants to or not. I’ll need to learn to be quiet.

      1. The Sports Pig's Wife

        Sam –

        Be the “crazy dad” who comes out to everything your son does, regardless how often he rolls his eyes at you or tells you to stop embarrassing him.

        Although affectionally known as a “Sports Pig,” baseball is my husband’s favorite sport. Growing up, he was in Little League baseball for many, many years (and still regrets not playing baseball in high school). While his mom would often attend his Little League games, his dad NEVER made it to a SINGLE one. I found this very hard to believe since my dad served as an umpire in my brothers’ Little League (the story of my dad calling one of my brothers out is something of a family legend).

        To think your own dad didn’t care enough about you, or your identical twin brother who played on a different team in the same league, to make an effort to attend ANY of your Little League baseball games is just so very sad. You would think dad could at least make it to the one game per season where his twins sons played against each other; or perhaps the final games of their long Little League careers. Nope. Nothing. Nada. Don’t be that dad!

  14. I’ve often thought that now that i’m FIRE’d I could just go work in a bookstore or a game store and make money from my loves. But the reality is these would be close to minimum wage jobs and do I really want to do that 5 days a week?

    The answer is clearly no; now if there was some way I could walk into Barnes and Noble and just say I have a free morning can I come work for 4 hours, then that would be a different story.

    Unfortunately those jobs don’t exist!

    1. Well, I did that. Little did I know that working retail in a book store and a travel store would actually be that wonderful. I was freelancing from home (sitting at the computer) and thought I’d apply for a lark. I loved loved loved working in those stores. Was it perfect? No, the bosses were not always easy to deal with, wages were minimum, but the customers, co-workers, and the books and the travel goods, all fabulous. I also loved the physicality of the jobs. I only worked part-time, on holidays, and the like. I walked to work, worked hard physically all day, never sat down, took pride in doing a great job, talked about books/travel to great people all day, and walked home again (30-60 minutes each way). After about 7 years, the book store chain closed, and the travel store was sold, and I was ready to retire to travelling the world. You never know until you try it. (I also got a big discount on purchases).

  15. Sounds like you had a lot to offer, and the results speak for themselves! Congratulations to you, the rest of your colleagues, and your team!

    A thought, in case you haven’t considered this… Write yourself the recommendation letter you would like to have the Head Coach write on your behalf (a ‘to whom it may concern’ salutation). Include real metrics, and date of Championship, as well as the more subjective qualities you brought to the team. Print two hardcopies for the coach to sign (one for him, and one for you) and have the softcopy loaded up to send to him on e-mail in case he would like to make changes.

    But he will probably be grateful for the work having been done for him, all the details included so he won’t have to look it up to struggle to remember and leave something out, still fresh, etc. This is a great arrow to have in your quiver! Well done, Sir!

    1. Great tip! It’s so easy to forget our accomplishments after a year or two goes by. I have written down some specific things that I did that allowed us to eek out 4-3 victories. It’s funny, because one of them is a rant because I was never acknowledged for some Critical coaching changes that helped one doubles team win.

      So much strategy and mental warfare is involved in team sports.

  16. My son is quite young at the moment, but he already had his first season of T-Ball. Boy are 4 yearolds fun to watch. I think next year I will try to help out as well.

    Your other comment about the money and your reaction to it is something that resonates with me. I would say it as, it’s work if they have to pay you to do it. Even if you choose to do it, the mindset of someone often is that you must give the value. Basically, I am repeating your words with mine because I feel the same way, and wanted to say that, a bit more wordy.

  17. Congrats on such an incredible series of wins, wow! That’s so awesome to be able to coach a team to that level of victory! I can understand how the shuttling of kids back and forth and having to drive to long distance away games can take the fun out of it. Volunteering next year sounds like the perfect plan!

  18. I was going to say a dream job is running your own business but you said it at the end. I keep myself busy with work and I would say that employing other people and helping them succeed is one of the most satisfying feelings. After opening my own real estate brokerage it really hit home that I am responsible for many people’s livelihood and it was not a feeling of burden, but of pride.

    I do not do well working for other people. lol

  19. Congratulations on winning the championship. That’s like a movie. Nice job.
    I think a dream job includes a higher purpose – like winning the championship. If you can keep the higher purpose in mind, it will give you the motivation to keep going. Self employment is the best because you don’t have to answer to anyone.

    I’m thinking about volunteering to be a coach for our little league soccer. It looks like fun, but I’m a bit busy with my mom’s health right now. Maybe next season.

    1. Thanks! It was an amazing feeling, one that I wish I could have chronicled better in a post. But at least Ive got pictures and a picture album a parent gave me to always remember the time.

  20. Simple Money Man

    This reminds me of when I played tennis in high school. Our coach and a couple other players with DL’s and cars would take the team to matches. We would all chip in for gas. Tennis doesn’t get the financial backing/love like basketball and football.

  21. Marie Jacobs

    This is my biggest fear holding me back from leaving the paid workforce completely: that I become so used to a relaxed schedule and low stress I can no longer stick out uncomfortable situations in order to reach my full potential. I have had several volunteer positions over the past seven years and had days at all of them where I wasn’t feeling it but stuck it out. Even volunteer posts feel like a just a job you don’t want sometimes. Being used to stress and very long days and feeling uncomfortable really helped me accomplish my goals of serving my family, employer AND community. If you care about the people you serve it’s hard to walk away even from a volunteer post. Maybe easier from ungrateful spoiled teenagers? I work mostly with elementary school kids and get paid in hugs, often from kids who don’t get enough attention from their own families. The need is great. With every one so busy and between drug testing and background checks it’s much harder to find volunteers now compared to 15-20 years ago, especially for leadership positions. Very few are willing to take on extra stress and responsibility even for worthy causes. Often the work is done by the same already busy people until they burn out or develop health issues. Many hands make light work and I am grateful for every person who uses their time and talents to make their community better!

    1. Absolutely it is harder to walk away from volunteering after you’ve made a connection. I enjoy volunteering my time at the foster care center. I should do so more often, especially if I’m going to do less coaching.

  22. I’ve been an assistant high school soccer coach for the past 14 seasons. I enjoy the extra cash, but definitely don’t do it for the money. For me its as close to a dream job as I’ve found b/c I feel like I am able to make a real impact. The bonds that form within a team last a lifetime, and beyond sharing soccer skills I’m able to teach the guys a lot about life. I’ve received positive comments from both parents, and former players that confirm my role. I don’t really view it as a responsibility, but rather an opportunity!

  23. ” … the closest thing that comes to a dream job is working for yourself.” and making enough money to feed and clothe the family. And possibly the odd international trip :)

    Can’t agree more, but I do believe as well that sometimes it can be good to be working for someone who inspires you, pushes you and helps you grow. I will admit those kind of people have been few and far between in my career, but those that I have worked with have had lasting impressions on me and helped me grow personally and professionally.

    How do you get that stimulation with your current endevor?

  24. Great story Sam. Although it isn’t a dream job, you accomplished something truly special with these kids who will remember this championship fondly for the rest of their lives.

    Being financially independent gives you the flexibility to donate your time on a schedule that works for you and your family. Enjoy!

    1. Thanks! It was as much a special moment for me as it was for the kids and the parents. I’ve kept this post on ice for four months because I wasn’t quite sure whether it was a good idea to disclose that I’m quitting. But I think volunteering is a great solution.

      I didn’t want to take this win for granted and forget about it. Winning it all truly was a great accomplishment because the school has been around for over 45 years I believe and had never achieved this result.

  25. This is an issue a lot of people relate to. Funnily, my husband likes structure and having a boss (his words! ) but I feel exactly what you describe Sam. The moment there’s money or obligation or responsibility involved, I start to lose interest by talking myself out somehow.

    A dream job for me is giving me access to an all you can eat buffet at the end of restaurant closing time :) I always dream being tall enough to model but that’s a pipe dream because they’re far from being creative bosses and are more pieces for display and not content.

  26. Turning your hobby / love into a profession always has downsides. When you’re doing it on your terms you get to skip or downplay the not so fun aspects. As you learned once you convert a hobby to a job, it quickly can lose some of its appeal.

    That said, I think it’s good that you did coaching. In addition to getting your medal, it’s important to use some of your time to help others. It’s especially good when the people you help are in no position to pay you back.

    You never know. A few years from now one of those kids might get serious enough to go pro. They’ll remember those seasons when coach Sam helped them improve their game. Then you’ll get to tell the story of how “I totally remember helping him/her improve their two-handed backhand”.

    That would be priceless.

  27. Wow Sam, you must be one hell of a coach to take a team to the conference finals the first year and then win it all the second. Kudos.

    It does sound like if you are getting paid you feel “obligated” whereas volunteering frees you up more to enjoy whatever endeavor you are doing.

    Awesome that when you do move to Hawaii you will be highly sought after as a tennis coach with or without that glowing letter of recommendation as you have already established an impressive resume.

    I do think there is now pressure to repeat as champions which may impact your enjoyment of coaching in subsequent years but man if you can create a dynasty that would be awesome. Best of luck!

  28. And when you have to answer to someone, you’ve got to alter your behavior.

    Great post, this is the crux of the matter. It can sound selfish but most of us ultimately wish to not have to alter our behavior. To be ourselves. Whether it’s work or just hanging out in a social situation, what’s better than just “be yourself”. But as you point out all jobs at some point throw a fly in that ointment. Or come with some downside.

    Now that I’m semi-retired and working from home on my side hustles for half of the week, I’m also slowly discovering the downsides of that as well. It can get lonely, and the struggle to maintain motivation is a real struggle.

    1. That is the line that jumps out to me as well! To succeed in Corp America for a full career you have to “not be you”. More bluntly you have to be phony…..play politics, kiss the leaders ring….etc! We all have to start somewhere but how long we have to do it is the question!

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