Seven-Year Switch

Had I stayed at my job two more months, just two more months after seven-plus years, I would have been eligible Jan. 1 for a four-week paid sabbatical. This was announced as a new policy to reward four years of service.

So technically — although this almost certainly would not have worked in practice — I could have timed my sabbatical with my eight-year mark and taken two in a row. Bridge in some holidays and stockpiled PTO, and I would be paid to travel for a quarter of 2019.

That’s the dream, right? I don’t know. I was talking about traveling with a friend who recently started his own company, and he had a refreshing counter perspective. Of course it’s fun to see new places and eat and drink, but he gets more out of being productive.

Traveling after winning the lottery is indeed the dream. Traveling when there’s work to do afterwards is not even close to the same. Take for example my five-month employment gap at age 26. I went to China, tried out for a game show, got to be an extra in a Disney pilot because they were looking for ethnic or “ethnically ambiguous” looks, and read a few random books. But for the most part, I hit the gym in the morning and library all afternoon to find my next job.

With a solid savings account buoyed by steady unemployment checks, I could have just chilled at the beach all day. I was relatively young and relatively unattached, with the time to do whatever I wanted. Maybe spending it at the library showed just how dreadfully unimaginative and conservative I am at my core, but it’s what I gravitated toward without any outside pressure or personal resolutions.

It’s just kind of hard for me to relax when there’s something that needs to be done in the near future. This blog post, as another example, added an antsiness to all my fun time during Thanksgiving break because I force myself to write one per month and the clock was ticking.

So yeah, although a sabbatical or two next year would have been amazing on various levels, the notion didn’t appeal to me as much as figuring out my next career move. I had been thinking about exit routes from the ad agency world for a while, and the timetable was about to be involuntarily accelerated after a conversation with my new boss back in May.

It ended up not happening, but determining a new path for me elevated in my mind from nice-to-have to think-about-at-night. I started by simply browsing a wide swath of companies and positions, figuring there are so many out there I’ve never even heard of that could be a great fit.

Not so much. I am comfortable making the sweeping statement that most jobs suck relative to what you could be doing with the free time. This must be why they have to compensate you to show up. I am highly skeptical when people say they would do their job even after winning the lottery.

It does pose a constructive question though. Are there jobs out there so fulfilling, I would do them for free? Follow your passion. Do what you love and you will never work a day in your life.

Hmmm. I don’t know what that means. I love chicken and broccoli because it’s the surest way to get shredded. But I don’t want to be a farmer or bodybuilder.

I love basketball and tennis. But any league willing to take me will require that I’m the one paying them, which doesn’t seem like a financially viable career. I was a sportswriter for a bit, but chasing quotes wasn’t as fun as chasing balls.

I love sex, but again, I think I would have to pay the people I really want to do it with. Besides my wife of course. And the only people who would pay for our sex tape would be unconditionally supportive family and friends, and we would just give it to them for free anyway.

Maybe going down the list of hobbies and interests isn’t the way to approach it. Maybe the purpose of a job is to enable you to have the life you want, which could mean a tolerable workday 9 to 5 while living in a city you love, supporting the family you love, and doing the things you love 5 to 9.

My mom has worked in sales at the same computer wholesaler for a quarter century. In her words, does she like her job? No. Does she like shoes? Yes. And her job lets her buy shoes.

I get it. However, it’s a little too linear even for my pragmatic mindset. There are lots of ways to buy shoes.

Here’s where I netted out. I’m 34 and have a lot of work hours left ahead of me. It is a finite amount though. And the uneasy yet guiding question for me turned out to be: What do I want to spend my next seven years working on?

Like I said, contenders were hard to come by, especially when I couldn’t really define what I was looking for. My suggestion for anyone in the same boat is to avoid the mental treadmill of trying to figure out a career through analysis and reflection, and just keep looking through what’s actually out there. Instead of seeking answers to nebulous questions about meaning and purpose and making top-down decisions from there, put real work into exploring concrete options and draw your conclusions from the bottom up.

I didn’t know I was looking for fintech and an ability to help everyday people. Econ classes in college made me feel as dumb as IKEA instructions do, and I haven’t volunteered for Habitat for Humanity in five years.

Yet I found a company that I believe will occupy an entirely different tier on my Maslow hierarchy. I told my wife about it and declared I was going to keep pursuing a job there, whether it took weeks or years.

The name of the company is Acorns, such a good name for a micro-investing app. Mighty oaks from little acorns grow.



Acorns is best known for rounding up your purchases and putting the spare change into a diversified portfolio of stocks and bonds. Ashton Kutcher, who has crushed early-staging investing with a bunch of startups including Airbnb and Uber, was asked by Stephen Colbert what his next hit might be:



The round-up feature is one small part of the big picture. Acorns just launched a retirement product and sold out preorders of an innovative debit card made of tungsten, the heaviest non-radioactive element. The mission is to build an entire financial wellness system for up-and-coming folks to save and invest.

This is a staggering problem. Seven out of 10 Americans don’t have $1,000 saved up for an emergency, yet their bank will ding them $35 for an overdraft fee. It’s a f___ joke with a sorry punchline.

For those of you lamenting the political times, BlackRock CEO Larry Fink traces the anxiety and polarization around the world directly to a lack of secure retirement prospects and financial tools. In terms of social impact, I don’t know how you can get more fundamental than empowering people to have the future they want. Plus I find personal finance inherently stimulating. I could explain Acorns to a stranger in a bar with genuine energy, which I think is a solid litmus test for job fit.

So that’s what I want to work on for the next seven years. I started this month as director of business development, tasked with brand partnerships.

Brands on our platform reward people for shopping with them by depositing cash forward, instead of cash back, into their Acorns account. This is a unique way to reach new and lapsed customers and build a relationship with a millennial audience adept at tuning out traditional advertising. Acorns charges the brand, and our shared customers get their investment frictionlessly. Everybody wins.

My role at Acorns is comfortingly familiar in some ways and refreshingly new in others. I feel hokey calling it the proverbial dream job, but it does feel like all the experience and work over the last decade led me to this happy opportunity. I can’t think of another company in the world I would rather join.



Writer’s note: If you spend any amount of your finite time reading the absurdities in this blog, we are either friends or highly compatible strangers. Thus I feel close enough to ask for your email address below. The only email you will ever get from me is one blog post per month for the rest of my life, until you click Unsubscribe. Thank you.