Your Advice on Working Multiple Jobs!

I’m transitioning back into working 3 jobs, one of which is full-time, this January. It’s been at least a year since I’ve worked multiple jobs, so I’m looking for advice about how other people do it. I figured an episode on advice for juggling multiple jobs might be useful to a lot of people.

I’m particularly interested in the following things:

  • Making sure you get facetime (digital or real life) with both teams, without making them feel like they’re a backburner priority when you’re there
  • For service or other variable shift work, dealing with scheduling needs and communication
  • Switching gears between multiple jobs
  • Juggling meeting schedules and competing deadlines between jobs (i.e. one job has a board meeting while the other has a lunch, how do you choose?)
  • Mentally/physically Separating email and google docs and slack between jobs

Something I’m also interested in is solving the puzzle of “other” life stuff when you have multiple jobs:

  • Childcare/rearing
  • Exercise
  • Social time
  • Meal planning, cooking, cleaning, and other home-based priorities
  • Professional development or education beyond office time
  • Side projects/hobbies
  • Volunteer work

What worked for you? What would you do differently? Were there things you hired out or other lifestyle changes you made?


This will be the first time I have the luxury of “more money” when working three jobs instead of “barely paying my bills”, but things I’ve found have worked before:

  • Having one job be a set schedule (say 6AM - 12PM) and the other be flexible, rather than 2 shift jobs
  • If you have a variable schedule job (like service industry), making sure to ask for a night/morning off perpetually where you aren’t working the other job so that you can schedule things like meetings/friend hangs/etc
  • Having a calendar with blocked times available and made clear to both jobs so meetings don’t get scheduled when you’re out of office - but use one as your main calendar so you don’t miss meetings!
  • Being the person who sets up quarterly meetings at your job (so that you can sneakily conform to your schedule)
  • Separate workspaces for each job if you use the same computer
  • Snacks. Seriously all the damn snacks. Working doubles/commuting across town I would spend a king’s ransom on burritos if I didn’t haul all the snacks

I guess I have usually had multiple jobs, but generally they were one full-time job with one or two other very part-time jobs. For me that feels very different (and much easier!) than working two moderate part-time jobs, even if the number of hours worked is the same.

With working one full-time job and one very part-time job, I always made it very clear that my full-time job was my priority and the very part-time job had to work around my full-time job schedule. I would generally only give very limited availability at the part-time place and was willing to walk away if needed. Some situations that have fallen into this category:

  • Working a M-F, 8-5 job and waiting tables one weekday evening and one weekend day
  • Working a M-F, 8-5 job and subbing at a library job on occasional weekends
  • Working a full-time, irregular hours job, and working as a nanny two mornings per week
  • Working a full-time, irregular hours job, and working on a substitute basis at a different job in the same field

For a while I had two ~25 hour a week jobs and that was much harder. I did three days per week at one job and three days per week at the other job. Part of it was difficult because really each job had enough work to have been full-time but they could only pay for 60% time. The only saving grace was that they were very similar jobs, so I was able to re-use a lot of the work I did from one for the other (this was a unique situation where that type of thing was totally ok to do). Even then, I kind of had to decide which one was my priority. (I had been working at Job A for 3-5 days per week for shorter shifts and a somewhat variable schedule. I got offered Job B for 3 days per week on a regular schedule. Job B was closer to my house, had more room for advancement, and paid more. I went to Job A and asked if I could switch to 3 days per week and a regular schedule or I said I’d have to leave for Job B. They wanted to keep me so they agreed to make it work.)

So basically I’ve always had the one job that was the priority and the other one(s) that knew they were secondary.


My multiple jobs are all under the umbrella of my own business so that makes some things easier in a lot of regards but I have found it absolutely critical to have boundaries around my time. I can’t be working on designing and then stop in the middle of something to jump to my consulting work and ping pong back and forth. When I do that I end up making no progress on anything and it’s frustrating.

So I try to schedule things even when they don’t necessarily have to be scheduled. I work from home which makes it tempting to not do that, but I get way more done when I do. So if I say the mornings are for the clothing business and make a to do list, then lunch, then afternoon is consulting with it’s own to do list. That way I can answer honestly about when I’m available when the inevitable client phone call or email comes in that needs me or whatever pops up. Grouping things together like that helps.

I’m also doing childcare during all of this so I have to be flexible that some days I’m not going to get much done. Those days I pack as much as I can in during naps and try to do what I can when she’s awake. That’s not ideal but it is reality for me. Fortunately I’m in a pretty good rhythm that I can get work done and keep the baby happy, engaged and entertained most days.

Oh another thing that’s just occurred to me is having a clear stopping point. Since I work from home it is really easy to “one more thing” myself into working until 3am/skipping dinner/not taking time for a shower etc. so I build in things that force me to stop. My nights to cook dinner help me plan my day to be done by a certain time. Knowing that H is relying on me to cook puts enough pressure on that I don’t keep working. When I lived alone I was bad about this and it’s only now that I’m doing something about it, mostly due to the tiny human that I can’t flake on (why was it ok to flake on basic needs for my own self? Idk)


Seriously, if we prioritized ourselves half as much as we prioritize other people, most of us would take much better care of ourselves.


I work 3 jobs now, and have an intensive physical hobby (I run ultramarathons). I have a full time job that is about 35 hours per week and has benefits but not great ones (glorified front desk at a vet office — I also do some things with social media and our scholarship program). Then I work two shifts a week (about 12 hours, with options to pick up additional shifts) at a running store. Huge discounts and occasional free race entries support my hobby, and I like some of my coworkers a lot and generally enjoy it. 3rd I pet sit through a small local company. This week I did 5 nights of overnight dog sitting as well as a big handful of cat visits, cause holidays, but usually I do much less: I can accept or deny sitting opportunities at will, though I generally take on a bit more than I probably should.

None of these pays well (except holiday pet sitting, cause tips plus holiday surcharges!), but they fit together nicely. The pet sitting is really flexible. If I need a break, I can (in theory) just not accept jobs. One thing that helps me is that all three of my employers are small businesses owned by cool people, and they’re pretty understanding. My full time job is the priority for meetings and the like, but there aren’t many of them, and if something gets scheduled late and I already have a commitment with one of my other jobs, I’m not expected to bend over backwards to drop it. Oh — I guess it makes a difference with that too that I’m hourly everywhere, so no one can reasonably expect me to be available when I’m not on the schedule.

Working exercise in is great for me because I run my commutes. Saves on transportation too. I do pay for a pricier gym for strength training and go to early morning classes twice weekly: the gym is less than a mile from my full time job. Where things get complicated with fitness is if I actually want to drive and do a long trail run, or when I do a race. Finding places for that in my schedule is a pain.

I do like the feeling of security I get from having 3 jobs, like something could happen with one and I could likely piece life together with the other two while I figure out a better plan. I don’t (yet) have the best emergency savings, but I’ve tried to build little protections in my life so it’s not likely I’d be entirely without income for any significant period of time.

My situation though doesn’t require a salaried position or any job that has a lot of meetings, projects, big deadlines.

1 Like

Do you see friends or are most of your friends running friends so your hobby/social time/running store job kinda fills the “friend” niche?

(i wish that I could figure skate my transportation, just do a double axel on the way to work…)

1 Like

Most of my friends are running friends, but I do (sometimes!) see them outside running (earlier this year game of thrones watch parties, meeting for coffee or a picnic, having folks over for dinner). Most would say my social life isn’t so robust, but I have a lot of friendly interactions that don’t feel like strict client interactions at both the vet and the running store, and I have friend/coworker overlaps at both those jobs as well.

1 Like

So yes, for the most part running and running store fills a lot of the friend niche.


This is the one I’ve struggled with most, and where I think I may be able to offer some advice:

  • A change of clothing helps marvellously. Even though I can wear what I wore to work to podcast/screencast/write, something about changing clothes helps me flip that switch in my head.
  • Use commute time between jobs to prepare/review for the next one. This is really handy when you have meetings to walk straight into, but also good for focusing the brain.
  • Don’t be too strict about things. There will always be spillover, I try to capture everything and have a daily “process inbox” time where I put things back into the right boxes.

I’m sure you have used all of those before, but that’s my two paw prints worth!

For this, I do the work once a week. David Allen said in GTD something about only having to think once a week, and I realised some time ago that I don’t like making decisions when it comes to picking what I want for lunch tomorrow/today, and that means that I end up skipping lunch or eating poorly. So once a week I plan what meals I want to eat, add them to a plan based on my current schedule, and try to batch cook a few things. Some days I’ll come home from work and record a podcast, have half an hour, and then another podcast so I need to know I have food to eat in that half-hour which helps motivate me!

Currently, I’m searching for a time turner. I’ve been told this isn’t available though. My side projects have suffered this year (I wanted to release a course, which is all planned, soemwhat written, and not at all recorded), but other things came in between. I’m definitely looking for advice on this!


Oh wow, everything you wrote is fantastic. Especially this bit:

I look forward to reading lots more of your thoughts around here!

1 Like

Thanks! Here’s to a great 2020 with multiple jobs! :smiley:


They all were smashed in a battle at the ministry, apparently. Still not over it.


I don’t think I’ll ever be over it!

I think about this more times a week than might be healthy. That and all the things I could get done if I could evolve beyond the need for sleep.