Why I Quit My Most Lucrative Side Hustle

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).

I believe I might have the right qualifications to say, "No thanks!"

I might also have the right qualifications to say, “No thanks!”

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.



  1. Good on you for holding strong on your position to travel the country and truly enjoy yourselves outside of the confines of work. Maybe in a couple years you’ll be looking to settle down for a year or so and take on some work, but so long as you’re having fun on your tour, no need to clutter up that enjoyment with jobiness stuff. Con calls and business travel? Yeah, no thanks.

    Keep the photos coming! 😉

    • Agreed — no thanks to conference calls ever again! Work may play into my plans at some point in the future, but not while we’re traveling, I’ve decided. Too much to manage!

  2. This is the exact reason I think Mr. T should quit his real job NOW. Then he can figure out a situation like that one and do it before he gets into your position: ready to stop working forever with excellent prospects. Having those prospects now would be more ideal! 🙂

    • It could have been a really great situation if we weren’t busy with so many other things right now. I wonder if there’s a way to explore those opportunities before dropping the full-time job?

  3. Glad to hear that you didn’t give in and start working again just because the conversation would be hard! Even though the opportunity may have sounded interesting, if your heart isn’t in it it all never provide what you are looking for!

    • You’re right, Thias — I probably should have seen the outcome coming from the beginning. There are enough people out there successfully traveling and working part-time remotely that I thought it was worth the shot… but I don’t think I was ready for that lifestyle yet.

  4. It’s interesting how by staying dedicated to your values and being less available you seemed to become more and more desirable. Goes to show many people have more leverage with their employers than they think.

  5. Kudos for turning down such an offer and staying focused on you travel plans.
    When the priority now is to travel and have fun, the something that feels like a job is probably not a fit. Good that you stay on as advisor, with the door open… I a year or longer, if travel feels like work (would that b possible) you could always return.

    I then assume the Trip to Turkey is still on? In case you consider going to the land of beer and chocolate, you know where to find me!

    • Thanks, amber! I’m still excited about what they’re doing, so staying on in an advisory capacity should be fun. We did decide to continue with our trip to Turkey, yes! I’m afraid we won’t make it to your area this time (could you make it sound any more appealing, though? Sigh…), but next time, it’s on!

  6. Stories like this make me want to pull the plug a little early. I know I could fill the void with some consulting work, but I also would want to be 100% remote but it would be hard. I bet it’s very reassuring that you made the right choice when you get offers like these. Take care.

    • Quitting has opened my eyes to a lot of new opportunities out there. At this point, I’m confident I could fill a part-time schedule with consulting projects and easily cover all my living expenses and then some. I wouldn’t even need to be FI to have that lifestyle. It’s a pretty attractive option!

  7. Your experience gives me a lot of hope for the future. We are still digging our way out of debt, so our plan is to switch to flexible, part-time employment in 5 1/2 years . . . because we won’t be able to save up enough to fully retire. It’s good to know that there these opportunities are out there.

    • I’m glad to hear that, Harmony! It’s a great option to have — and we may pursue it more in the future in light of the fact that I’m FI alone but that we’re not FI together right now. People like Tamara and Chris at Nomads with a Van are doing quite a bit of remote work and still able to travel full-time; pretty cool!

  8. Sounds like you made the right decision. I want nothing more but to be able to quit my job and travel. Im working on it, just not there yet.

    • I have no doubt that you’ll get there quickly. It’s worth the journey, that’s for sure. Congratulations on your wedding, by the way! Sounds like it was lovely, in spite of the rain 🙂

  9. Sounds to me like there was some not so subtle manipulation going on with your friend. It seems like he did everything he could to reel you in. If one way didn’t work, he tried another. And you did absolutely nothing wrong. Staying on in an advisory role is perfect. It keeps you informed about something important to you, without having expectations or demands placed on you.

    • Haha, yes. I’ve worked with him long enough to know that he is a natural salesman, and this felt similar to the way I’ve seen him recruit others in prior work. I’m hopeful that the advisor role will be more comfortable, though I do expect the sales pitch to join full-time will continue!

      • I should add that he’s a good friend, and I do think it’s all genuine — I think that’s just his style!

  10. I think of this as such an important cautionary tale! We were recently explaining our plans to some friends we’d never told before, and the guy said something along the lines of, “I’m sure if you want to pull off something bold like that, you have to be the type of person who is awesome at your job, really hard working and a totally desirable employee. I’m sure it will be a total surprise when you announce you’re leaving.” Your post is that personified — of course people want you to work for them, and that will probably continue until you have a truly long resume gap that renders you obsolete. But yeah, the slippery slope! Mr. ONL and I have been talking a lot about this recently, wondering if we could quit this year if we keep one or two clients on a freelance basis. But my feeling is: I don’t like “working us.” We don’t spend enough time together, we’re too stressed out, we eat crap, we don’t sleep enough, etc. I think even one freelance gig that pays enough to support our basic needs would infringe too much on the healthier, happier life we’re trying to shape.

    • I definitely need to get better at saying “no.” It’s fun to explore the world of opportunities in concept, but actually doing the work when we’re traveling is a different story! I think I’m also learning that I’m not a good part-timer, at least when doing the same type of work I’ve done during my full-time career. Like you said, even a part-time/freelance gig changes the flow of our days meaningfully. I think I would rather be “all in” or not working at all.

  11. Good going dude. Definitely made the right decision as you don’t want those responsibilities eroding your fun travel time. You really need to be able to relax and enjoy that time.

    • It was worth trying, I think, but we’ll keep ourselves focused on enjoying every minute of our travels for now. There will always be more work opportunities later should we choose to pursue them.

  12. Allan Liwanag

    June 4, 2016 at 10:03 pm

    It’s good to know that you stood by your position. It’s a good lesson to never pursue something that your heart and passion aren’t. Because in the end, you’ll be the one in an awkward position.

    • Good point, Allan — I probably should have seen this one coming from the start. Definitely something I’ll keep in mind in the future.

  13. When you least expect it. I mean that’s great the opportunity came up, but will it get you to where you are going any faster or will it do the exact opposite and drag you back in?

    • Ha, the latter, clearly! I don’t regret giving it a shot. The spirit of this adventure is to be open-minded to a variety of new possibilities. This one didn’t work out, and I’ll try to build on what I learned from it.

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