Jumping off the side-hustle treadmill: harder than I thought

For most of the last decade, I’ve had at least 3, if not 5, jobs simultaneously. From a side gig delivering bagels at 6AM, to building nonprofit databases, to parking bikes under an aerial tram in the freezing cold at before the sun comes up, I don’t feel useful unless I’m always working. Having multiple hustles going simultaneously helps financially, too, when my hours get cut, or grant funding is lost, or a freelance gig ends.

Working like a dog [35/365]

Sometimes it was a nightmare scheduling all the jobs: get up at 4:30 to go to my first job until 10AM, ride 6 miles to second job, work until 4PM, ride 5 miles to 3rd job, leave at 8PM, come home to a pile of invoices to do for freelance work before bed at 9:30PM. There wasn’t really the concept of a “weekend”. On top of all the jobs, I was on 5 civic committees, 2 non-profit boards, plus producing a podcast and doing a daily photography project.

In May 2014, I finally got a full-time job with benefits (hallalujah!), but it took 16 months to finally stop working all my other jobs. The excuses varied why it took me so long to quit the other 4 jobs:

  1. I kept working one of my fundraising jobs for 2 months, racing there after work, because we were in the midst of a membership campaign.
  2. I kept delivering bagels on the weekend for 11 months, even though I didn’t *need* the $25 cash; it kept me in shape, and got me up before 6AM on the weekend.
  3. I kept working as Zine Librarian for another 13 months because I said I’d do it for 3 years when I took the job. I had projects I wanted to finish up, and I had a 24-hour event to plan and a library computer game to build, dammit!
  4. I kept working as a database consultant for a year because I had some outstanding projects I wanted to finish for clients, and because it’s surprisingly (winkwink) hard for most nonprofits to replace a freelance database consultant at only $13/hour.

The stress of having all these jobs was breaking me – working 70+ hours a week, and nothing was ever totally done. I was always behind on something for someone. I broke up with the (lovely, smart, caring) woman I was dating because I just couldn’t handle another commitment- human or professional. I would put off doing laundry for weeks because I wouldn’t get home before it was after quiet hours in my building. Scheduling a weekend trip required finding someone to cover for me at one job, and working double at another to make up the hours before I left. My arthritis and my acne, both of which are exacerbated by stress, had gotten the worst of my life. But working can be addictive, especially for a Midwesterner who’s taught that hard work without complaint is the only path to righteousness.

I started to trim down, both in jobs but also in volunteer commitments – I left all but one citizen advisory committee (once I realized I was on a subcommittee of a committee I’d been assigned to by another committee) and I resigned a non-profit board I was no longer effective on after 5 years. It was agonizing to quit each one, though. Endless pro-con lists. I briefly took on another freelance consulting gig because I really like the people involved before finding there was no way I could schedule it around my full-time 7:30-5 M-F schedule. The rest of the team had no full-time jobs taking up most of their time, and finding common meeting times alone, let alone hitting deadlines was impractical for me.

My new year’s resolution was that by the end of 2015 I would achieve 1-1-1: one job, one civic committee, and one board.

And in August of this year, I had finally achieved my goal. I made a verbal promise I wouldn’t pick up another side gig until at least January of 2016. At first, it was liberating. On weekends, I would surf pinterest for hours. I started sewing my clothes. I slept 8 hours a night, every night. I stopped drinking coffee. I got through my 17-month backlog of mending in a 7 hour marathon. I checked out 15 or so books out of the library each week. I organized my kitchen cabinets. I cooked dinner with fresh vegetables almost every night. I’d sleep in until 7:30AM on Saturdays and realize that I used to be arriving HOME from one job at that time, about to start a conference call for another.

But quickly, I started to get bored with the “free time”. I didn’t know what to do when I came home from work. And I was never rushed to finish any side projects, because I knew there was more free time to come. I was watching far too much television, drinking far too many manhattans. There’s only so many personal finance blogs to read and going to bed tipsy after watching 3 consecutive episodes of Chuck doesn’t actually make you feel that good about your life.

I began to stare with envy at folks with side gigs, thinking how nice it was to have something productive to do on the weekends – the Handy cleaner, the Postmates delivery person, the catering temp. I didn’t know what to do with my free time that wasn’t volunteering or starting a new job, so I started going to work earlier and earlier – what used to be a 8:30AM start time crept to 8AM, then 7:30AM, then 7AM, without leaving work any earlier at night. I started to put together what I had gained from having multiple side-gigs: the concept of time-boxing.

Work expands to fit the time you have available.

When juggling side gigs, I had hard deadlines to go to my second job by 5:30PM, or leave work early for a committee meeting, or not schedule weekend meetings over my side gigs. I made sure my full-time gig was doable in 45 hours a week, most weeks. Without that, my full-time job has started creeping up to fit the time available. Rather than always been stressed about being behind on one job or another, on weekends I pace around, worried about my full-time job. I end up breaking down on Saturday afternoon and start working on emails or designing posters, even though I’m already at 50 hours for the week. I love my day job, but there’s no variety any more: working 60 hours a week fundraising is not the same as working 40 hours a week fundraising, 5 hours a week delivering bagels on my bike, 15 hours organizing zines.  Everything is always urgent, and everything is the same. The creativity of the side hustle boogie is gone. With one job, it becomes Metro, Boulot, Dodo*, as they say in France.

Somehow, with the least work commitments of my adult life, I’m feeling the most stressed out I ever have about work. The stress never leaves now: I dream about my job, I go to bed making lists of tasks for the next day, and I wake up already feeling behind in work.

So I’ve got 7 weeks left in 2015, which will be the hardest weeks of the year at my job (nonprofit fundraising jobs, are universally the craziest in the last quarter). And then in 2016, I’m finally allowed to have a side gig again. I’m already signed up to volunteer doing taxes, plan a conference, and potentially help get a podcasting network off the ground. Maybe I’ll start delivering for Postmates or start writing the personal finance blog I keep dreaming of. And I can’t wait. I’m just not a one-job pony.


*Translates to “The same old routine, the daily grind”. Literally: subway, work, sleep. Or in my case: Velo, Bolot, Dodo. (Bicycle, work, sleep.)

24 thoughts on “Jumping off the side-hustle treadmill: harder than I thought

  1. Thank you for posting this – I’m in the “5 jobs situation” and was just nominated to be on a non profit board… And I keep thinking “maybe I should just go back to school for nursing and just have ONE job” The two times I’ve had one job I’ve been fired… Yet I am praised for my determination and talent when I am juggling so many things at once, and completing all of my tasks… The thing that keeps stopping me from nursing school is that I’m not sure I could actually just do one job, I think I would be completely bored with the monotony of the same thing every day. I need to have projects to work on, and new goals to reach. I’m starting to realize we are not alone, and we are also very talented – not everyone can juggle so much. This week I ended up in the ER from the stress of my many jobs (and didn’t even realize the physical toll it was taking) so, maybe I need to take a vacation or two, but, I think it’s ok to have multiple things going on at once, sometimes it’s how some of us thrive.

  2. I forgot to comment on your post about the panic attack, but with no history of anxiety, that still struck me as very close to home. Sorry you had to go through that. I definitely would love to figure out the balance of multiple jobs BUT not uber-stress. Maybe we should get together for coffee and figure out some sort of philosophy of accountability :-P

  3. You and me are exact opposites in this regard. I actively resent the fact that I have to work for a living, and refuse to do a job that bleeds into my non-working hours or doesn’t have a definitive start and end to my day/tasks.
    That said, I’m not making enough money to do much more than pay rent and eat right now, so I should probably look into Postmates or something like it.

  4. Think of the positive – when you let go of the other jobs, it allowed on of the thousands of people in town that are unemployed to pick up some badly needed shifts. (Hopefully what happened! We’re thinking positive here!)
    Then you can spend more time on your freelance and make sure you’re taking time for selfcare! As I can relate though can’t imagine when I get stressed and overwhelmed my joint pain flares up and I almost can’t even function or move due to fibro. I try not to let that keep me down (as I’m also on 2 committees, work f/t and then moonlight harp gigs and various other endeavors as well as almost biweekly dr appts) – but of course if there isn’t self care and social time everything falls out of whack

  5. I never even considered the possibility that I might want to give up my side hustles one day… and if you’d asked before I would have called you crazy. But after reading this, you’re really making me reconsider the idea.

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