Making the Most of a Crappy Job
When you can't exit, there's still room to grow
Welcome to the latest entry in The Captain’s Log…
I’m your host, Bob, and my mission here is to share personal, behind-the-scenes stories of ups and downs from my career leading tech startups and corporate innovation.
I write to make you think, smile and discover a shortcut to success or a trap to avoid.
Here we go…
Sometimes we’re stuck in a job—and have to stick it out. We’ve got college debts to pay, a new baby on the way, or family health issues to juggle. A big bonus or vesting stock grants can keep you stuck. Or you might fear that leaving a job before the one-year mark will make you less hirable in the future.
These are the times when the alarm clock is especially evil. You trudge into the shower, and as the water falls over your head, you do the math on how many days are left before this prison sentence may end.
Sound familiar?
I thought so…
These trying times are a test. We tend to forge on, check the boxes, and close the laptop at 5 pm—sharp. “Quiet Quitting” is just a new name for something people have done for years. But there’s an alternative that I eventually get to after a few days or weeks of whining: Find something positive to focus on besides the endpoint. Even in the worst jobs, working for horrible bosses, we can choose to elevate our game and come away with something positive.
“I made a big mistake.”
It’s a Tuesday afternoon, and I’m on Zoom with Sarah. We have a mutual friend who asked me to meet with Sarah and share any advice I have on what she should do about a tricky career situation.
Sarah works in sales in the marketing+tech industry, and she starts our call with the winning smile and high-energy required to win in this challenging role. But her energy and smile fade quickly as she describes her dilemma:
“I’ve been in bigger companies for my entire career and got impacted by a layoff at my previous company. With the entire industry making cuts, finding a new job took much longer than expected. I ended up accepting a position with a smaller startup. A few warning signs flashed during the interview, but I ignored them because I needed to pay the bills. Unfortunately, things have turned out as I feared. The product is not ready for prime time, and my boss—the CEO—has little time for me and seems disengaged overall. I want to quit, but I’m worried a short stint here will look bad. And I need to refill my bank account.”
After quickly agreeing that this is a crappy situation, I can’t help but think about the bright side. I tell Sarah that there is some good news here. First, she’s proven her spidey job sense was right. She’ll know to listen to that closer the next time. Second, she has gotten some direct experience with a small startup for the first time in her career. She’s learning about the pros and cons in a way that a textbook or friends’ advice could never match.
I also try to make her feel better about a potential quick exit. I’ve hired many people over the years and now run a recruiting business—which enables me to see how many other hiring managers think. Generally, we all ignore a short-term stint unless there are multiple examples. You just need to have a good story/spin on the situation.
But I probe further, asking Sarah if she likes anything about this new job…
“I’m selling a digital out-of-home product that’s pretty innovative. The company has me calling on consumer brands, the industry norm. But I’ve got several B2B clients from my previous job that it could work for with a few tweaks. The CEO doesn’t understand this market, but he’s not stopping me.”
As she speaks, I see her smile and energy return. Sarah is back to her old self—excited about a product and helping the clients she worked with previously. I stop her there and suggest that she might have found the solution.
She could focus her activity on blowing out this B2B use case. It would play to her strengths and passion, thus increasing both the chances she would hit her number and be more energized on the job. It would allow her to rekindle relationships with previous, trusted clients. And at the worst case, it would provide an interview story that would excite her next hiring manager. For example: “The job was not a good fit, but I decided to make the best of it. I found an entirely new market based on my previous experience and delivered incremental revenue to the company.”
Sarah loves this idea and tells me how she might bring it to life. She even sees the positive in her disengaged CEO—he won’t stop her from trying it. I’m sold.
Survive and Advance
How did I come up with this advice on the fly? Because I learned it the hard way myself.
Back in 2018, I sold my second company. There was a 19-month earnout before my team and I would get our final equity checks. It was a larger company that seemed strong from the outside and through our reverse due diligence. I saw a bright future for the company and thought it could be a place I might stay for many years. I even bought six figures of the company’s stock on the open market.
But just a few weeks in, I realized I wouldn’t be staying a day after that final check cleared.
There’s no reason to detail the reasons in this post. Put simply: I’d rather live with my own dumb decisions and execute someone else’s dumb decisions.
And my stock purchase would barely be worth five figures today. (Thankfully, my financial advisor now nudges me away from individual stock purchase ideas.)
Anywho, I didn’t love my new company but had to suck it up for another 17.5 months.
So I sat down one Saturday morning and decided to strategize. One option would be to rest and vest. Our business was on track, and I had unlimited PTO. I could only be fired for doing really bad stuff. Maybe 4-hour workweeks in Hawaii would be the solution?
But that’s not me. I’m a builder, not a rester, and I couldn’t imagine letting my team down by heading to the beach. So I asked: What can I do to make the most of this time? I came up with three answers, which I put into action immediately:
Watch and Learn - This was a +1,000-person public company in the tech space, and I was getting paid to sit in the middle. So I took notes. 165 pages of notes. I wrote about what went right and wrong and analyzed key leaders and their decisions. When something blew my mind or pissed me off, I immediately opened this journal and jotted it down. Aside from reducing stress, writing helped me understand how the big company world works. And it gave me LOTS of fodder for this Substack. Don’t worry about me running out of stories to tell here!
Grow my Network - I got to engage with many new people as our product was integrated with our acquirer, many of whom were stars. I knew this would be a chance to build trusted relationships with new, sharp, and experienced people. Years later, many of these employees have left the mothership and are spread across the industry. And not a week goes by that I’m not giving or receiving help from the people I met during this time.
Have Fun with My Team - Our company was successful and worth a premium acquisition price because of the team we built together. I have never worked with a group that was so in sync. But I knew that it would end after our earnout. The Borg always assimilates. So I encouraged us to savor our magic as much as possible in our remaining months together. I basically became the Chief Culture Officer at the office. I kept people pumped, protected them from the Borg, led impromptu happy hours, and helped people think about their future careers.
This focus got my head back in the game. I no longer dreaded the alarm or counted the remaining weeks, days, and hours in the shower. We maxed our earnout and had a lot of fun in the process. And while I wish like hell that this company would have been a long-term fit for me and more of our teammates, the last line in my “acquisition journal” summarizes things nicely:
“I got priceless personal value from this acquisition that eclipsed its financial value.”
You Always Have a Choice
Just yesterday, I spoke with Chris, a regular reader and sharp leader that I crossed paths with several years ago. We caught up on life and traded a few career war stories. Completely unprompted, Chris told me that his current company ended up being less rewarding than he imagined it would be going in. So he decided to “Go around and find the smartest people who work here and learn from them.”
Chris gets it. Quiet quitting is giving up—a habit that can cause our skills and minds to atrophy and make us a lot less fun to be around. But we can reframe work in countless ways to turn negative into positive. We can even quietly nudge our jobs closer to what brings us joy when our bosses aren’t looking. Then we can quit…while we’re ahead.
As always, thank you for reading and sharing my posts. The more subscribers I get, the more motivation I have to keep writing!
Bob Gilbreath is a 2x-exit entrepreneur and co-founder of Hearty, a curated matchmaking service that combines top software developers with early-stage, venture-backed startups.
Another good read, thanks Bob Gilbreath!