Practical WordPress Development

Setting Routines and Boundaries for Self-Employment

About four months ago, I received the following comment on one of my blog posts:

I’d love to hear some thoughts, maybe in a future post, on setting boundaries and establishing routines. My ideal would be to have already been to the gym, at my co working space and starting work by 8:30, finished by 6pm, no exceptions. Despite my best laid plans, I haven’t been to the gym in 2 weeks, I find myself starting work any time between 7am and 11am, and occasionally working late into the night once my son is in bed. Some people dig this freedom, but I find that I crave some structure – I just reject having it imposed on my by an employer.

For some time, I’ve sat on this particular topic because it’s something that I’ve wanted to write about, but either had a backlog of other things I wanted to cover, or it didn’t fit with the type of content I was trying to publish at the given time.

Boundaries of Self Employment

yes – working near your tv is risky business!

But now seems like a good time to look into this: Partially because I’m preparing a few posts that are dealing with a number of tools that I use to get things done, partially because a number of people I know who work from home have shared the same feelings, and partially because this is something that I’ve been doing for the past seven years or so.

But for those of you who want to skip the entire post, here’s the TL;DR:

It depends on your personality type.

Honestly, though, there’s more to it than that.

Boundaries for Self Employment

When you begin to talk about self-employment, people are generally interested in things like how you structure a business, how you manage payroll, how you deal with taxes, how you manage insurance, and all of that kinda stuff.

This post is not that post.

Instead, this post is meant to answer the points above:

  1. “Setting boundaries and establishing routines.”
  2. “My ideal would be to have already been to the gym, at my co working space and starting work by 8:30, finished by 6pm, no exceptions.”
  3. “I haven’t been to the gym in 2 weeks.”
  4. “I find myself starting work any time between 7am and 11am and occasionally working late into the night.”
  5. “Some people dig this freedom, but I find that I crave some structure.”

First and foremost, I think there’s a lot of psychology wrapped up in this as well as personality traits. I’m an expert on neither (surely, for those who have read my stuff, know that by now), but I’ve had many of the same challenges so I thought I’d share how I dealt with each of the above issues. Again, this is no guarantee that it’ll work for anyone else, but I figure it’s worth sharing.

1. Boundaries and Routines

By nature, I thrive on structure and routines. My wife and I are completely opposite in this regard (and she’s loosened me up a little bit which is a good thing), but the number one thing for me to having a successful working environment at home is to have a place that is solely dedicated to work.

If I use my laptop to work anywhere in the house, then each room has its own set of distractions be it my kids, my television, a magazine, some books, or whatever. To combat that, I have a room setup that is specifically my office. The door stays shut when I am on a call or focused on something (during which my wife can just text me or, you know, bust open the door if it’s an emergency).

It has everything that I need to do to get work done and nothing more. This consists of a coffee maker, my computing equipment, some workout equipment (more on this in a bit), and a couch that’s predominately dominated by my dogs.

2. Co-working Spaces

I don’t do so well in co-working spaces. Perhaps it’s because I tend to be more introverted or perhaps I simply feel more comfortable in my office, but my house is my best and favorite place to work.

Sure, there’s a lot to be said for social interaction, but when you’ve got some young kids at home along with your wife, all the while you have the ability to Skype a client or one of your teammates, the social interaction aspect isn’t quite as challenging. At the same time, I know none of that compares to real people-to-people getting work done.

The thing is, I don’t focus as well unless I’m in my home office zeroed in on what I’m doing. As such, the idea of working elsewhere doesn’t sound appealing to me at all (and I’ve tried it numerous times at numerous places and never gotten in a groove).

The point I’m trying to make here is that if co-working is optional, try to make a place at home that is yours and that is built around what makes you the most productive.

3. Working Out

The only workout that I’ve ever been consistent about is running. It’s by far my favorite form of exercise, and although I’m not able to do it as much as I used to anymore, I still try to fit some time in each day.

The thing is, it takes time to get your gear together, to change clothes, to get out the door, to get back to the house, and basically settle back in. Nothing beats running outside and if your schedule allows for it, then great; otherwise, purchase in some equipment that you can use in your office.

For example, I’ve a treadmill, a tower (used for pull ups, push ups, and all that fun stuff), and a set of dumbbells all in my office. Usually, when I have about a 30 – 60 minute break in the day in between my calendar and my TODO list, I hop on the treadmill and run for a bit. There’s a television in the office that’s connected to an Apple TV so I’ll normally stream something from Netflix while I’m running, but prior to that I just used my iPad.

This way, I save money on gym costs, I don’t have to travel, and I save time by being able to work out at home.

4. Starting Work on Time

People either get up early and start work, or they sleep in and start work later in the day (of course, the latter case, they’ve usually been working late into the night so I’m certainly not knocking any of that).

The truth is, until we had kids, I was more of a night owl, too. After that, though, everything changed. Now I tend to get up early, am usually at my desk no later than 7am, and will work until 5pm most days (sometimes later, but it really depends). There are still those nights where I have to run a second shift to compensate for what I didn’t finish earlier in the day, but I think that comes with the territory of self-employment.

Sure, you can choose not to do that and I think there’s a case that can be made as to why this isn’t something you have to do, but I’m simply sharing my personal experience. One of the key things about this is that you have your spouse, partner, or whatever bought in the idea that there will be some nights where, say, after dinner or after watching a show, you have to return to work for a bit.

Other than that, I’m pretty rigid with my time: My alarm goes off at the same time every day (and I hit snooze a few times), I get up and do the usual morning routine, sit down, and start working. The order in which I get stuff done usually depends on how I’ve structured my reminders, but there are also surprises that come up along the way. To that end, you just have to learn to roll with it rather than get sidetracked and irritated about it.

5. Structure

It’s almost counterintuitive that those of us who are self-employed, at least in this industry, crave structure though we want it on our terms versus, say, that of an employer (and that’s not to sound disrespectful). I’d bet now, more than ever, employers are more relaxed with working schedules and remote work more than at any time in history, but I digress on that.

Anyway, as far as structure is concerned, you’re self-employed so you have to be self-structured. You are the one who is responsible for ordering your life, responsibilities, tasks, and environment in such a way that it’s conducive to getting work done.

This doesn’t just mean having all of your equipment in a room or being able to turn up your music as loud as you’d like, but this also means having the discpline to turn off the things that are distracting during the day. Perhaps it’s Twitter, maybe it’s IRC, or maybe it’s even some random app or set of apps on your phone.

Whatever the case, they need to be prioritized and open only when you’re able to handle the demands that they may place on your time. Anything other than that can damage the structure that you’re after.

And That’s My Story

I have absolutely no idea if this read like something that was interesting and helpful or if it was something that sounded more like incessant ramblings about things that don’t matter, but considering that they are answers to questions that I’ve been sitting on for far too longer, I hope it’s more of the latter.

There’s no single right answer to this. The key thing to remember, though, is that you’ve got to make sure that the structure you setup for yourself is compatible with your personality and is conducive to getting work done.

If this means working at a co-working spot after hitting the gym at 11am and headed home at 7pm, then so be it. Conversely, if it means getting up before 7am, working out at a random point in the day, and wrapping it up at 5pm, then so be it.

With all of that said, I’d love to hear what the rest of you have done with your home offices, or even your co-working spaces, to make sure you’re getting as much done as possible each day. I’m always interested in hearing how others structure their stuff around work – especially those who are self-employed.


  1. David Yarde

    Great article Tom!

    Part of my daily routine includes leaving the house and coming back as if I’m going into the office, and the same in the afternoon to close out my day.

    By doing this I’ve found its easier to get work done because I’ve placed myself in work mode. A simple but effective routine.

  2. Eric Dye

    You have confirmed much of what I’ve found to be helpful. I also think personality can play a part in it, and as a rigid person myself, I’ve found that with a little time flexibility that I can get the same amount of work done with a whole lot less stress.

    Thanks for sharing, man!

  3. Grant

    I find myself craving that separate room you’ve got. I’m an introvert as well (although slowly changing) so I haven’t found co-working to be terribly effective plus I hate the travel time to the city everyday.

    At home I currently only have the one desk/computer for work/social/gaming/TV/Movies/etc and the lines blur as to what I’m supposed to be doing at a given moment in the day. Waiting till I can move out and dedicate a room just for working.

    I’ve been getting into running more and more and try for a 5-10km run/jog during the day which helps clear the mind, getting around 2 of those a week at the moment.

    • Tom

      I find myself craving that separate room you’ve got. I’m an introvert as well (although slowly changing) so I haven’t found co-working to be terribly effective plus I hate the travel time to the city everyday.

      I used to be an extrovert but really grew more introverted as I got older. Anyway, I will say that having my own office at home is nice. Works really will given the situation with the kiddos and such :).

      At home I currently only have the one desk/computer for work/social/gaming/TV/Movies/etc and the lines blur as to what I’m supposed to be doing at a given moment in the day. Waiting till I can move out and dedicate a room just for working.

      Ah, I know that feel. I actually had to reduce gaming a lot the older I’ve gotten. I have an addictive personality so as my responsibilities have increased, my gaming needed to decrease; otherwise, I’d not be doing so well managing the usual day-to-day stuff :).

      That said, I don’t mind streaming B-movies during the day (though I generally am listening to music), but I don’t want anything that I’d want to specifically dedicate all of my focus. Unless I’m on the treadmill – then I don’t mind :).

      I recently started watching Twin Peaks, but that’s probably content for an entirely different post.

  4. Tim Brand

    I get asked the question of how my wife and I do it all the time. We have five kids, all with special needs, we home schooled (until this year), work out together, share an office together and manage to run two successful businesses in the meantime.

    My answer is that we don’t do everything, we do everything we can. This post is awesome for helping those people that really want to look at the in and outs of running your business from home. Some will have it “easier” than others but easy is all in what you make it.

    Really glad you shared this topic, I’m super stoked when I get to read about other people and their at homes businesses.

  5. amy

    I have been having trouble waking up before midday. I have just started to be self employed and the lack of routine is not working. My bf works until late so our time together is usually between 12-2am. He sleeps at 3am and wakes up at midday too. Ha, I have fallen into his night owl routine and it’s hard to crack. But maybe I am being too hard on myself to fall into the same routine as everyone else. I do exercise I swim from 9-10pm, I fit everything I need to do just into a different time zone than the rest of the world.

    • Tom

      If that works for you guys, then great! If not, then it’s a slow conversion into developing new habits.

      It can be done, but it takes time. I don’t think it’ll literally happen over the course of a day or two :).

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