After Five Years Of Unemployment, I Finally Found A Dream Job!

I remember going to Airbnb’s Friday afternoon happy hour back in 2012. My college buddy’s wife worked as an assistant chef and invited me over.

The office wasn’t very large and Joe Gebbia, one of the founders, was horsing around with a wig held together by a white headband. After speaking to Joe for about five minutes, I decided Airbnb was a great place to work. I applied for some random finance manager job, and got rejected. Undeterred, I proceeded to apply to three other Airbnb positions because I strongly believed it was going places. No luck.

To put things in perspective, in 2012, I had just left my corporate banking job of 11 years (13 years total with two firms). My severance took care of my living expenses and I was making a livable income stream from Financial Samurai. All I wanted was to try new things and joining a tech company in San Francisco seemed like the logical next step. I had no tech skills, so I knew I had to take a step down in pay just to get my foot in the door.

If I got the job, I’d be a relatively rich man now because back in 2012, Airbnb was worth $2.5 billion. Now, Airbnb is worth somewhere around $30 billion, and Joe alone is worth close to $4 billion! Realistically, I would have probably earned a modest (for SF) ~$100,000 a year salary and received a standard $100,000 – $150,000 option package that would now be worth $1,000,000 – $1,500,000. Not bad when the company finally goes public.

Since my Airbnb rejection, I’ve applied to around 200 Bay Area tech jobs. Company names include Google, Apple, Facebook, and Uber. I even applied to a dozen Series Seed and Series A startups. None of them were ever the right fit. Although I’ve done stints as a consultant for three fintech startups, I’ve never once been offered a full-time job.

It’s one thing not being able to find a job during a recession. But can you imagine going for five years during a bull market, spending a hundred hours applying and interviewing with companies and never succeeding in getting one of them to love you enough? You start questioning what’s wrong with you. Granted, I probably didn’t show as much enthusiasm as a regular job hunter, but still.

Accepting reality is a tough cockroach to swallow. But facing reality is what we must all do to survive and improve as people. Don’t give up. Keep searching for the right fit. If somebody doesn’t believe you’re good enough, try to understand why and consider creating your own destiny instead.

Related: Career Advice For Those Interested In Joining A Startup

A New Job Awaits

As luck would have it, I got an e-mail from a tennis club buddy of mine whom I’ve been playing doubles with for the past five years. He said there was an opening at his son’s high school for an Assistant Varsity Tennis Coach and wondered whether I was interested.

What’s nuts is that I had just written about how I should become a USPTA certified tennis instructor to see if I can add value as an assistant tennis coach at one of the private grade schools in Honolulu in order to increase the chances of my unborn child getting in. Ever since I lived in Manhattan in 1999, I’ve heard so many war stories about how admissions is simply impossible at the grade school level.

I can’t expect my child to be smart, talented, and hard working. But I do expect to do my best to help my child get the best education possible. One way to improve my child’s chances of getting into a school is to see if I can add value to the school in the field of writing, online media, online entrepreneurship, or tennis since I can’t compete with most families on money.

Eager to learn more about this new opportunity, I followed up with my friend’s referral and applied. After a two-hour long interview with the Athletic Director and the team’s co-captains, I got a phone call the very next day with the job offer! My work entails coaching the singles players, providing strategic advice during a match, and instilling in them a FIRE to never quit due to a lack of effort.

They can lose to a more skilled opponent who is bigger, stronger, and faster. But they will not lose because they didn’t drill enough cross court backhands or hit enough serves.

Why I Accepted The Job

Assistant coaching pay isn’t lucrative – about $5,500 over a three month season that entails 1.5 hours of practice each day, travel time, and team matches that may last as long as three hours. But, I’m not doing this for the money. I’m doing this because:

1) I love tennis – everything from playing, to watching, to figuring out strategy. I’m a guy who went to the U.S. Open alone one year and watched tennis from 11am to 11pm for four days straight. I spent $800 for one second round French Open ticket, and $1,200 for one second round Wimbledon ticket to fulfill my bucket list of seeing both Rafael Nadal and Roger Federer play on center court before they retire. I’ve played three times a week for the past eight years and won’t stop until my knees break or my shoulder falls off, whichever comes first!

2) Help make a difference in a young person’s life. Playing a sport teaches a kid how to work hard, compete, adapt, lose graciously, and win humbly. These are key attributes for success in any professional endeavor. I want to be there to help kids grow up to be awesome members of society. Everything starts with how we nurture our youth. One of my 2017 goals is to “really make a difference in 12 people’s lives.” I originally measured this goal by the number of out-of-the-blue e-mails or comments I’ll receive from readers telling me that so-and-so article really helped them be happier or financially more secure. With 12-14 members on the varsity boys tennis squad, maybe I can now make an impact with at least three or four of the players!

3) See what it’s like to have a teenager. I’m a preparer, mostly because I realized long ago that I know very little about how to do anything I’ve never done before. The key to never saying, “if I knew then what I know now” is to simply seek advice from someone who’s been there. When I write about having kids or getting an umbrella policy if you have a teenager, I’m pontificating. By coaching these young men, I’ll get a better idea of how teenagers think and how I can be a better mentor and parent in the future.

4) Decide whether private grade school is really worth it. I’m a big proponent of public school, having gone to public high school (McLean), public college (William & Mary), and public graduate school (Berkeley) after spending the first 13 years in international private schools. But I’ve come to the conclusion that if you can afford private grade school (gross income = at least 5X annual tuition), you might as well send your kids to private, despite everything being free online. I want to see with my own eyes the value of private school now as an adult, by the way they teach their kids. I’ve already read all their course catalogs, college placement statistics, and taken a tour of the campus. The tuition for this SF-based high school is $48,150 a year, which makes the Hawaiian private schools at $20,700 seem like a bargain!

5) Build a network. Relationships are everything. People simply want to do business with people they know and like. I would never have been considered for this job if I didn’t hang out with the University of San Francisco’s head men’s tennis coach for hours at a tennis tournament one day. We just bumped into each other one Wednesday and he observed my enthusiasm for the game as we got to talking about everything tennis. The USF head tennis coach happened to be giving my doubles buddy a lesson recently, and my buddy asked if the coach knew anybody who would be interested in the high school varsity assistant tennis coaching job. Both men knew the Athletic Director at the high school and recommended me. Of course I still had to interview, but it helps when you have strong referrals.

The other cool aspect of this job is that I get to meet the ~60 other coaches who work at the school. It’s a completely different world from the financiers, rideshare drivers, startup workers, and online media friends I know. I’m excited to learn from veteran coaches and hear their stories. Just like that, I’m part of this great organization which has produced wonderful alumni for several decades. Perhaps there will be great insights I can share with all of you in the future as well.

6) Enhance a resume. I’m never too proud to start at the bottom and work my way up. And if you are too proud, please read: Spoiled Or Clueless? Work A Minimum Wage Job. Let’s say I do a good job as an assistant coach for the next three years. Maybe I’ll be considered for a head coaching position one day from this school or another school. Or maybe by then, I’ll have a pre-schooler and we’ll want to move back to Honolulu to be closer to family. Perhaps Punahou or ‘Iolani might think I can add value to their tennis programs given my CPR training, concussion training, and three years of varsity tennis coaching experience plus 30 years of playing experience. With such value-added services, perhaps my kid may have an easier time getting in.

7) An incentive to stay in shape. A main goal for everyone who has achieved financial independence is to try and stay as fit as possible. To die young after building enough passive income to permanently pay for life would be a crying shame. Having a job that makes me run around the tennis court and be surrounded by athletes is very motivating to stay healthy.

8) Experience new challenges. There’s a fun saying, “If you’re coasting, you’re going downhill.” I’m determined to build Financial Samurai for two more years so that I can have 10 years of entrepreneurial online media experience under my belt. After that, who knows. But I’ve found myself faltering in entrepreneurial intensity ever since I took a month long tour to Asia in 2015. So many people were happy with so much less, the trip reminded me to focus beyond online traffic and revenue.

I am admittedly nervous about my first day on the job. It feels exactly like the first day of school. I hope the kids like me. And I hope we can have lots of fun!

Think Near And Far

Steve Jobs said, “You can’t connect the dots looking forward you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart, even when it leads you off the well worn path.”

When I look back on my life, it’s crazy how so many things happened without my anticipation. For example, by getting waitlisted at UVA, I never would have met my wife whom I met in Japanese 101 class at William & Mary. I couldn’t imagine my life without her! She got into UVA and thank goodness, decided not to go.

If my net worth hadn’t gotten slaughtered during the financial crisis, I never would have started Financial Samurai and left the corporate world in 2012. I’m also so thankful that in 2011 I was not promoted to Managing Director in 2011. Otherwise, I would have absolutely stayed on for at least five more years, if I didn’t get laid off first.

The only consistent attributes I can think of that have helped all these years are:

• Work ethic – never fail due to a lack of effort.
• Always looking at the positives of failure.
• Adopting an unwavering belief that everything will turn out OK.
• Focusing on helping others first before asking for anything.
• Being mindful of the suffering of others.
• Showing gratitude.

Always think about how your actions today might affect you in the future. It’s helpful to think in 5 or 10-year blocks. By thinking near and far, good things will eventually start happening.

Recommendation: If you’re looking to leave a job to do something more meaningful, learn to engineer your layoff to get a severance instead of quitting. If you get laid off, you should get WARN Act pay, potentially a severance, unemployment benefits for up to 26 weeks, and COBRA healthcare. If you quit, you get nothing.

Update 2019: We got to the finals of the NCS conference in 2017 and lost to a school three times bigger than us. It was the farthest our school had ever gone. In 2018, we won our conference, got to the 2018 finals and won 4-3 against the team that beat us! Now it’s time to defend our title.