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
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
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.