Staying Motivated While Working Solo

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I recently started MeetSpace, a video conferencing app for distributed teams. It’s not the first time I’ve started a product company, nor is it the first time I’ve worked alone. But, it’s the first product I’ve worked on alone. In the past I had either partners or clients I’ve worked with on any project, but this is the first one where I’m the solely responsible person (insert irresponsible coworkers joke here :P ). In this post I’ll outline the ways that I keep myself motivated and working each day.

Accountable Person

One of the very first things I did was get someone to hold me accountable for my work. I’m very fortunate to have Brian Sierakowski of TeamPassword meeting with me weekly to hold me accountable. We also swap notes with what he’s doing over at TeamPassword.

Each week I tell Brian what I got done this week and what I expect to get done next week, and we compare it to what I said I’d get done last week. We also talk at a high level about strategy or sometimes just bat ideas back and forth. Eventually we just end up talking about video games.

It really motivates me to think about our weekly meeting (it’s on Friday morning) during the week. I know I’ll have to tell Brian if I miss a deadline on a task, especially if it’s something that’s not particularly difficult but maybe a chore to do. Having it on Friday morning also makes sure I don’t leave it until the last minute, because I want to have everything done by Thursday, but I can finish it Friday if I have to.

I would highly recommend getting an accountable person to help you out if you’re working solo. You should have a regular meeting with a specific agenda that covers what you did and what you will do. Even if you’re a freelancer and all you track is billable hours, you can simply text a family member and say “I billed 35/30 target hours this week”.

Working Contiguously in Time and Space

It’s very important for my productivity to work contiguously, both in time and space. I need to go to a separate location that is solely a work location, and I need to be there for one long chunk of time. Context switching in and out of work mode doesn’t work at all for me. I have to go to work, work until I am done, and then go home and not work. I have a very binary work brain.

I worked from home for a while when I first started freelancing, but after a few months I got a work space. My friends at Figure53 were kind enough to lease me a desk at their office. Later on, I ended up working out of offices I leased or coworking spaces (I’m currently at Workbar Arlington).

When I worked from home, I was billing hourly to clients, and that kept me very productive and honest with my time. I would work in 30 minute pomodoros modified to be 30 minutes working 5 minutes resting, and I would bill that as 30 minutes. That way, I couldn’t stop working inside a 30 minute chunk or I wouldn’t be able to bill it.

But, once my time was my own, this didn’t work. It was too easy to make stupid coffee videos when I was at home instead of working. So now, I go to an office.


Having a regular routine and schedule is very helpful because it keeps my expectations set very consistently on how each day is going to go. Every weekday looks like this:

  1. Wake up (6:30am)
  2. Make breakfast (usually coffee and scrambled eggs)
  3. Bike to work (drive if weather sucks)
  4. Work 8am-12pm and drink 32oz water
  5. Lunch 12pm-12:30pm
  6. Work 12:30pm-4:30pm and drink 32oz water, second coffee if I want
  7. Bike/drive home
  8. Exercise
  9. Hang out (video games, movies, reading, cooking) and drink 32oz water
  10. Sleep

I have two 4 hour work blocks with a lunch break in between. There’s not much to do at the office that isn’t working. Because my schedule is really consistent, I get very used to following the same schedule every day. This way there’s less of a nagging “hey let’s go to work late today / come home early” voice because those are the times I always work.


I mentioned that I discuss my tasks with an accountable person, and in a previous post on minimum viable project management I discuss how I manage the tasks on a project. What this really breaks down to is a todo-list (I use Wunderlist) with all of my tasks on it.

Anything that I do goes into the list, and generally those items go onto the list at least the week before I work on them. Each week (after the Friday accountability meeting) I scrub my list. This involves going through every task and seeing if their due dates are all still reasonable.

All tasks have a due date (almost always a Friday). This groups tasks into weeks. I can look at the tasks for a week and if it’s too much I bump some tasks to the next week, and cascade forwards until the roadmap looks good.

I delete any tasks I don’t think are important any more. Sometimes I add something like “ooh, it would be neat if…” If on Friday I don’t think that task is really important, I delete it.

At this point, I have one to two months of roadmap. Anything farther in the future is so poorly defined I just keep it as a thought. By the time I get low on tasks, my favorite thoughts for the product will be at the forefront.

When I am working, I look at Wunderlist’s automatic “Week” list, which shows everything due within 7 days. This is my list for the week, and I work top to bottom, checking things off as I go.

I also make use of recurring todos for marketing. That involves writing inbound content, publishing, republishing, tweeting, emailing, and also customer development type tasks. That way these come back around on a schedule.

One really nice aspect of this system is that I can actually get to a done state. When I finished everything for the week my list is blank. I am actually done. It’s wonderful. I usually will take a Friday afternoon off if I’m done. Life is short.

Varied Schedule

I have a routine, tasks, and recurring tasks. This comes together to form a very regular day and week. But each day is a little different. I like to have different kinds of work scheduled throughout the week so that day-by-day I’m doing different things.

Mondays are for marketing, creating content, following up on campaigns, and customer development in the morning. This is really motivating work because it reminds me of why I’m working on MeetSpace: all the people! Seeing a good piece of feedback or good reaction to a post is very rewarding. Then seeing a bad piece of feedback or bug report is really motivating to do a good job. I can’t sit on my butt if there’s a bug out there!

Monday afternoons I work on bugs and then technical debt. This puts me on a “clean slate”. Tuesday and Wednesday I work on the “big feature” of the week. Thursday is another marketing and content morning. Thursday afternoon is wrapping up features, bugs, and technical debt.

Friday is my accountability meeting, any remaining tasks, task planning for the next week, a product update for users, and any leftover bugs or debt.

Not Naturally Motivated

I’m writing this post to share that there’s really a lot that goes into getting myself to do work each day, week, and month. It’s not something that comes naturally to me. If I am at home I’ll play video games. At work I’ll surf random internet sites or social networks or talk to coworkers. If I don’t have a combination of a time and place to work, tasks due, someone who’s going to ask about them, people who are interested in them, and a regular but varied schedule, I don’t get much done at all.

So if you don’t feel naturally inclined to get lots done every day, don’t worry, you’re not weird. You’re probably pretty normal. I needed a lot of structure before I could really get lots done on MeetSpace.

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