What are Eight Years of Your Life Worth?
A grown-up version of the Marshmallow Test. Could you pass it?
Welcome back to The Workaround. I’m Bob, your host 👋
You’re in good company with thousands of fellow entrepreneurs and innovators who read (or listen—see play button above) to my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
Lots of people I know are waiting for their exit.
They don’t love their jobs and dream of doing something else with their lives. But the promise of life-changing money keeps them in their seats.
Some are waiting for the IPO or their Private Equity owners to sell the company. Others wait for the options to vest or for the commission checks to be paid.
I see and feel for their suffering—because I’ve been there. In total, across two acquisitions, I’ve spent eight years of my career waiting for a check.
Neither case was “Rest and Vest”—we had to work our butts off to get those checks.
However, I learned that a painful journey can bring a reward more valuable than what hits your bank account. Here’s how…
The Value of Years
I was sparked to write this by reading Steven Schlafman’s post, “How Much is a Year of Your Life Worth?” He describes a conversation with an executive coaching client two years into a lucrative five-year earnout after selling his company in 2022. And he’s feeling the pain:
“I’m incredibly bored at work, just going through the motions. I’m using only 20% of my brain and 10% of my heart. I don't know if I can do this much longer.”
Steve shares how this is a common sentiment among his clients. They gradually lose themselves while hanging on in a company that is no longer theirs. Before becoming a coach, Steve experienced this while working at a VC firm, waiting three years for his carry to vest.
Steve then asks his client:
“How much is a year of your life worth, continuing in this way?”
The bold is mine because this is the real point. If you’re struggling, you can find happiness without leaving that check on the table.
My First Marshmallow Test
In Fall 2005, I was a partner at a digital advertising agency. Our business was growing quickly and profitably. We had just passed the $10 million revenue bar—which is typically when acquirers become interested. Digital was growing fast back then, and the major holding companies needed to catch up. So, they responded immediately when we floated the idea of selling.
We hired an M&A advisory team specializing in agencies to help us navigate the process. We received four offers within weeks, and a small bidding battle broke out. At the 11th hour, the company with the lowest initial bid doubled their offer and rose to the top.
But there was a catch: 90% of the deal's total value would be paid out after a 5-year earnout, depending on our ability to reach lofty revenue and profit goals.
There’s a five-year plan for you!
Our advisors explained that earnouts are very common in service businesses like this. Agencies can’t lock their customers into long contracts, and they lack typical competitive advantages. We tried to get them to negotiate a shorter period, but they knew it would be a no-go. I recall their old sage telling us, “Boo hoo, you have to wait five years to get a big pile of money before you turn 40.”
So, an adult version of the Marshmallow Test stood before us.
You know the Marshmallow Test, right?
It’s the psychology study of little kids to see if they can delay gratification. Put a child in a room and place a marshmallow before them. Say that you'll give them a second marshmallow if they don’t eat it by the time you return. Then, leave them alone for a few minutes.
It’s a no-brainer on paper—a 2x return on a few minutes of patience. But it’s a massive test for young kids. There’s lots of sighs and squirming. Long-term studies show that children who can wait for a larger reward tend to have better life outcomes as adults.
Here’s what our acquirer tested my group of 30-somethings with:
You can have this money now—in the mid-6-figures—and leave. Or you can stay and give up many other career and financial opportunities. You’ll get 10 times that money at the end of 5 years if you grow revenue and profit by 4 times what it is today.
Now, for those of you waiting on that PE IPO, banking on a verbal promise from your boss, or hoping the stock hits a specific price—note that this was a contractual agreement with the largest global company in our industry. The likelihood of your employer delivering on its promise should factor into your personal math.
It looked like a good deal, so we decided to pursue it. While we would have tremendous work ahead of us, we were confident in each other, our team, and the rising waters of the digital marketing shift.
Hell is Real
One thousand, two hundred, and sixty-eight days.
That’s the countdown calculation I came up with the first morning in the shower when I considered how many more days I would have to work at my agency before our payday.
I would do that calculation many more mornings in the years ahead.
Nothing in my work experience has been more challenging. I fell into this agency job only a year before striking this deal. If you’ve done work in this kind of business, you know the challenges…
Clients may fire you at any moment for any reason.
Employees can walk out the door at any time.
Bigger, sexier agencies constantly scheme to steal your clients—including our new sister agencies within the holding company that bought us!
The winds of the economy can shift client spending wildly—The Great Recession happened in our third year.
I thought working for my friend would be great, but it wasn’t. We haven’t spoken since I left.
The pain and paranoia took its toll on me. At one point, I reverted to wearing glasses instead of contacts. It was a conscious (crazy?) decision to put up a shield to separate and protect me mentally.
I wasn’t looking forward to getting the check. I was waiting to end my life’s sentence.
We Get to Make our Minds
Steve describes what I went through in his post:
“How much is a year of your life worth? Because the longer we wait, the more it costs us—not just in money, but in the vitality, joy, and passion that make life worth living.”
It felt like a black-or-white decision. Stay and suffer, or leave and be free. What is my life worth? The answer eluded me.
Nine hundred forty-six days…
Eventually, something else popped into my head in the shower. I can’t live like this any longer...but I can change my mind.
My misery was harming me and impacting those I love. I told myself to stop whining and take responsibility for fixing my emotions and situation. I decided that I would get more value from this experience than whatever the money might bring.
From then on, I found or created moments of learning, team bonding, challenge, and joy. I took the initiative to launch projects that piqued my curiosity. I published a book and did a speaking tour. I led a small team in a skunkworks product lab. I also found plenty of time for personal hobbies that I had ignored before the acquisition. Even sitting in meetings I didn’t enjoy gave me insights and experiences I treasure today.
Interestingly, they teach kids something similar to help them perform better on the Marshmallow Test (and for the rest of their life choices). Research shows that kids do better when they invent or are taught strategies to help them, such as closing their eyes, studying ceiling tiles, or counting how many seconds have passed.
Researchers have also proven that the skill of delaying gratification can be taught to adults. We just need better strategies. I’m living proof.
[Side note: Don’t say you do it for the team or your family. That’s an excuse. Blaming them is bound to bottle up resentment and prevent your advancement. Suck it up for yourself. This is your life test.]
We hit our earnout targets after just 3.5 years. Although they didn’t let us out of jail early for good behavior, I kept expanding my skills and even began planning my next startup.
Expanding the Game
I think it’s harder to keep people committed today than with our agency twenty years ago.
The world now has infinitely more options—and infinitely more threats. Trust between employers and employees is falling rapidly. Endless books, posts, and podcasts—including this one—push opinions on what we should do with our lives. The Paradox of Choice defines our age of stress. We can feel alone on a sailboat life raft amid an ocean of possibility—and danger.
But in such times, picking any direction can be best, especially one with a specific time commitment and high odds for a significant pile of treasure on the beach when you get there.
Years after my agency experience, I was thrown back into the earnout handcuffs when we chose to sell our influencer marketing startup.
This time, we found a way for all employees to take the Marshmallow Test.
We negotiated up to a $3 million carve-out for employees, which meant roughly a year’s extra salary if we hit our 19-month goal. Some of our investors and my long-departed co-founder questioned this idea, but we pushed it through anyway. After all, our success depended on every employee giving their all to hit some pretty aggressive growth numbers.
I wasn’t surprised when we hit our max target three months early. There’s nothing more powerful than a team united in a common goal.
Live. Die. Repeat.
My younger daughter was at home over the holidays. She’s about to finish her senior year out-of-state and will most likely begin her career far away from home, so any time she chooses to spend with us is special.
[Side note: It’s both precious and sad that the older your kids get, the more interesting they are—but the less time you get to spend with them…]
She’s been studying for a career in animation and watches movies to build skills for her future career. Over pizza one evening, I asked her why she watches the same films dozens of times, poring over books and YouTube videos about them. She explained that this helps her fully understand the choices made by their creative teams.
My wife chimed in to remind me that I’ve seen Groundhog Day and Edge of Tomorrow dozens of times each. I own multiple-format copies of both and routinely stop everything to see them again when they pop up on whatever streaming service I am scrolling through. So I asked myself: Why these two movies?
I think it’s because they remind me of the moral of my life story: It only gets better through struggle.
“Keep Buggering On!”—Winston Churchill
The protagonists in both movies get their butts kicked over and over again. They are sentenced to a life of waking up, screwing up, and restarting all over in the same spot. No one understands their suffering. In both movies, there is pain, but it doesn’t kill them. They are the Gods of that day, giving them a special power in presence. And by sucking it up and striving each time, like compounding interest, they get smarter and stronger.
Spoiler Alert…in the end, both finally find success and meaning—then break free.
In the movies, Bill and Tom didn’t have a choice. But in real life, we do. With determination and patience, we can make ourselves better each day, increasing our odds of success and giving us a lot of stories to reflect on when we retire from the game someday.
And there is an opportunity for heroism.
We choose to sacrifice what could be an easy life of enjoyment, to take the pain and make the effort to change the world for others’ benefit. Like protagonists in each movie, those around us don’t see the effort or pain we went through, but that’s OK. Most don’t do this just for the money, recognition, or other ego traps. We do it to make a positive dent in the world.
How can I help?
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The shared detail of resorting to glasses as a form of distance is a profound little piece of self-observation that makes for great storytelling. It conveys so much so effectively. We've just moved across town closer to my adult children for exactly the reason you describe, that kids we're bonded to age well and it just becomes more of a pleasure to be around them. And the fact that you've watched groundhog day, repeatedly, is more meta than my brain can handle this morning.