I didn’t expect to be doing a whole lot of work after leaving my full-time job in January, but it’s amazing how many opportunities come along when people hear that you’re not employed. Within just a few hours of updating my LinkedIn profile, I had multiple headhunters e-mailing about new positions all over the country – both full-time jobs and short-term consulting gigs. I’ve politely declined each inquiry to date, citing my busyness with “a variety of other projects right now” (primarily sleeping in, hiking, and drinking craft IPAs, but don’t tell them that).
Then, an extremely enticing opportunity fell in my lap. A former colleague, with whom I had enjoyed working previously, was launching a new company in a space about which I’m personally passionate and needed someone to lead the go-to-market strategic planning. It was the kind of job I would have jumped on, if only I were looking to go back to work.
“The mission and vision are very inspiring,” I told him, “but I’m not looking to take on a full-time job right now; we have a lot of travel planned and are really looking forward to a long sabbatical.”
I didn’t mention that I envisioned the “sabbatical” being years or decades long, or possibly permanent.
“That’s fine,” he told me, “and you should absolutely take time to travel and recharge. In the meantime, if you wanted to get involved a bit during your sabbatical, just let me know.”
I wasn’t eager to be working so soon, but I thought there was a chance this could turn out to be a dream scenario. I put together a brief (and perhaps outlandish) proposal: I would lead a few projects part-time, 100% remotely, primarily by e-mail (rather than phone), in exchange for a high hourly rate, plus equity vesting and full benefits. Oh, and you can pay my cell phone bill, too. Might as well ask for everything.
He didn’t even counter my offer. “Great,” my friend told me, “let’s get started!”
Shit! Did I even want this job?
I decided it was worth a try. If I could make it feel less like a job and more like a side hustle – dictating the hours, timeline, and workplan – it might be the ideal gig, with the extra income enabling us to travel in style perpetually.
As you may have guessed by the title of this post, it didn’t quite work out that way.
I could see the first red flag before the work even started: my heart wasn’t ever fully in it. Daniel and I were eagerly taking off on the first part of our road trip adventure, and I was having to carve out time to read lengthy industry documents and run financial analyses. Not my idea of a relaxing time. Our dirtbag camping lifestyle didn’t make things any easier, with unpredictable internet access and a limited power supply adding to the challenge. But with a few full days at Starbucks here and there, I was at least getting the work done.
About a month into the new gig, my colleague sent me an e-mail one weekend morning:
“I had a hilarious dream last night that you told me you decided you would work 15 hours a week indefinitely since you calculated that would warrant $48,000 a year, which would be enough to live on indefinitely in the mountain town you had found to call home!”
Yes, “hilarious.” That’s pretty much the vision. Had he been reading my blog? Probably not, I figured. If he had, he would know I could do it on far less!
The second red flag was the way the work evolved over time. I’ve seen it a hundred times before in other work settings – you try to set clear lifestyle boundaries, then they’re rapidly eroded. “Can you fly out here for a meeting later this week?” (Absolutely not; we’re in the middle of the desert, and I haven’t showered for three days.) “Are you able to attend this industry conference on the east coast next month?” (No.) “Let’s set up recurring biweekly conference calls to maintain our momentum.” (Let’s not.)
Perhaps I was naïve to ever think this gig could really look like a side hustle. If it looks like a job, and it acts like a job, it’s a job. It’s not my style to renege on a commitment so quickly, but less than two months in, I was already looking for a graceful way out.
Our upcoming trip to Europe mercifully provided one. “Considering what a challenge it’s been to work while traveling full-time domestically, I think it will be exponentially more difficult in a foreign country with a ten-hour time change,” I shared. I’d be happy to stay on in an advisory role, I explained, but I don’t think I can provide the quality of work the company deserves while we’re traveling abroad.
Then, the final red flag: “That’s totally fine,” my friend replied kindly. “I understand completely. Have a great time in Europe and recharge your batteries. We’ll look forward to your joining full-time when you get back.”
Whoa. Wait a minute. What?
Just like that, the whole relationship felt like it was turning into a disaster. I had never been 100% transparent about my FIRE plans, preferring to keep my financial life private. I had also never ruled out the possibility of working full-time again. But I had certainly never committed to joining the company in a full-time role, let alone with that timeline. Had I been leading him on? Was my attempt to maintain some privacy by not revealing the full picture really just lying? Or was this just a misunderstanding? Perhaps even a light sales tactic from a friend who genuinely wanted me on his team?
“I don’t think you should count on that,” I told him nervously. “We have a lot more traveling we want to do, and I don’t think our plans include going back to work this year.”
“All right,” he replied. “It’s good to know what you’re thinking. We would be thrilled to have you join, and we could craft whatever role would be most appealing to you. Let’s keep in touch while you’re traveling.”
I couldn’t help but reflect on what a bizarre pseudo-negotiation we had just had: “We’ll give you anything you want,” he seemed to be telling me. “Hmm… I guess I’ll keep thinking about it,” I coyly replied. Really, could the privilege I enjoy be any more obscene? There are millions of people out there looking desperately for work, and here I am turning down what most people would consider a dream job. I’m lucky to even have the offer, let alone to be in a position to say “no thanks.”
We left it there – still open-ended to the future but with me off the books for now. I’ll stay on as an advisor, primarily out of personal interest. That’s the way I’d probably like to keep it, barring some unexpected change in our plans. The extra income was nice, but the dream gig was not to be. It felt like a real job, not a side hustle, and it just wasn’t compatible with our full-time travel plans right now.
There are some things even a dream job can’t buy.