Working when you want is amazing & challenging

Some of the unique challenges and perks that come with being able to work when you like

In late 2013 I started working for Buffer as one of their remote engineers. It was my first fully remote job and the first that allowed me to completely set my own hours. This is very liberating but comes with a certain set of challenges.

I had written a post to mull over a lot of things going through my mind. I’ve included the original text of that post at the end of this article.

It is now 2017 and I am working for myself. This means I have even more freedom of how I allocate my time, it also means I have 4 years more experience with this sort of thing. I wanted to update/rewrite this post to show my current thinking.

My Situation

I am the sole person involved with tosbourn ltd, I have a mixture of client based development and CTO work, long running projects with other folk, and my own projects.

This means at any given moment I need to balance my time between these three groups. All of which are important for cash-flow and my long-term plans for the company.

The Challenges

  • I am working from home – which means when stuff happens in the house I kind of have to get involved, this could be if the landlord needs some building work done or if there are deliveries to be signed for.
  • I have a lot of different types of tasks – I assume many different roles in the various projects I am in. For some I am there to churn out code, for others I am there to advise and write code, I’m a project manager sometimes and a high-level planner others. It is a lot of hats with a lot of context switching.
  • I am on other people’s schedules – I have settled into working roughly 9-5 Monday – Friday, moving those times and days around to suit me when it makes sense. For some folk this is perfect because it is also when they work, but some of the projects I work with involve people who are doing it as a side project, which means just as I am winding down for the day they are starting to get excited.
  • My mental health – I have had depression in the past and still have very low days. When you are working for yourself this can have a big impact.

How I Handle These Challenges

The working from home issue isn’t so bad, I categorise the interruptions with the same sort of distractions you get anywhere. I’ve written about being pragmatic with interruptions before, if you’re interested.

The different types of tasks I handle by ruthlessly itemising everything in a todo app and using my calendar to block off time for each project in advance. This allows me to say with some confidence when I am next free. I leave plenty of space between items for the little emergencies and unexpected things that crop up during the day/week.

I find blocking off time especially useful for my own projects. So long as I can see that I have blocked off enough billable hours for the week, other hours can be spent on projects that will eventually provide lots of value. I am writing this post during one of those pre-planned blocks of time.

I still struggle with the other people’s schedules challenge, I try and communicate as much as possible so I don’t need to be actively involved in things “after hours”, but some level of this is unavoidable. If I know about things in advance I will plan my days around it. For example if I know we need to have a call for a few hours in the evening, I might start my day 2 hours later so I don’t burn out.

The way I reason about my mental health is that people are paying me to think, and if the thing I need to use to think needs some time off that is fine. If people were paying me to walk a horse around and the horse needed to sleep then no work gets done and that is a reasonable stance. I feel the times were I have focus are productive enough to make up for the times when I don’t.

I Really Like This Work

One thing that has really helped me through all of this is that I really enjoy being my own boss and I really enjoy the work I am doing for myself and others. This means the associated challenges are fun to solve and a lot of the work I find relaxing, so don’t mind if I accidentally slip into working extra late on something.


I mentioned that I am doing 9-5 Monday-Friday, which sounds like I haven’t picked my own schedule at all. It turns out that this is largely when I am most productive so it has suited me the best. I don’t go to sleep until late (12 or 1) so I like to sleep until about 8:30, then with regular breaks I find I am finished my days work by between 4 and 6.

Original Post

So I have recently started working at Buffer and the work is 100% remote, the work also doesn’t revolve around any particular time based schedule, it is more there is a body of work that needs to be completed and some of that work will be time critical but it doesn’t require you to be at your computer say between 9-5 Monday to Friday.

This is very liberating, it means if I feel like I would be more productive working more in the evenings or maybe early mornings I could easily do this, it also opens up a lot of questions, I want to openly discuss two of them.

The main one I can think of is how long should I work for? Both in terms of how much time should be put in over a week period but also on each day what should I do?

Previous jobs have trained me that core hours are between 10 and 4, so my gut feeling is at a bare minimum I should be doing that Monday to Friday, but that doesn’t feel like enough time to get good work done, so maybe I should start working the weekends as well? But would that burn me out?

I know from previous experience that after 6 hours of straight coding/concentration I am not going to be too more productive the rest of the day, so increasing that time seems like I would just be wasting energy without too much gain for the company or myself.

6 * 5 is only 30 hours a week though, like I say this doesn’t feel like enough to accomplish the various tasks I would need to accomplish, especially when you consider that some of that time each day will be spent catching up with the team and doing all the important non-coding work that us coders need to do in order to enable us to code!

I think an extra 6 hours would work well and would make me feel like I was contributing enough bum in chair time with the tasks I am being paid to tackle, so I think I am going to experiment with doing 3 hours on Saturday and 3 hours on Sunday.

The next challenge with being able to work my own hours is that I am a world class procrastinator, I could start doing research for a very particular problem and end up jumping around various places each time getting slightly further away from the task at hand and getting too high level with the problem.

I feel that I have two choices, change my nature to make me not procrastinate anymore or realise it is who I am and plan my work around it.

I think changing my nature isn’t really going to work, especially not short term. And I don’t think that what I am doing is bad, it isn’t like I verge into looking at cat pictures, I look at very work related stuff and improve myself as a developer as a result.

So how can I plan my day to embrace the fact that I am likely to stray off point if there are no time pressures. I figure one way to do this is going to be to give myself artificial time pressures, if I know I only have two hours to complete a task, you can be sure I will not veer much further than a useful blog post or a StackOverflow question/answer.

So I am thinking maybe something along the lines of;

  • Monday - 8am - 10am, 12pm - 2pm, 4pm - 6pm
  • Tuesday - 8am - 10am, 12pm - 2pm, 4pm - 6pm
  • Wednesday - 8am - 10am, 12pm - 2pm, 4pm - 6pm
  • Thursday - 8am - 10am, 12pm - 2pm, 4pm - 6pm
  • Friday - 8am - 10am, 12pm - 2pm, 4pm - 6pm
  • Saturday - 11am - 1pm, 2pm - 3pm
  • Sunday - 11am - 1pm, 2pm - 3pm

That means that I have a lot of ‘down time’ between these short bursts of work, I plan to use this time to do various things;

  • Errands that I would normally do in the evening, freeing up my evenings a huge amount.
  • Dedicate time to going to the gym without feeling guilty I am skipping work.
  • Read the higher level stuff I would have been reading if I thought I had all day to finish a task.
  • Chill out with my fiancee when she is off work.
  • Have focused time to read, I am guilty of doing this in the evenings when I am too tired to really appreciate or take in what I am reading.
  • All the while in the back of my mind I can be churning over the next problem I will be solving in my next two hour window.

By the way - in case you are thinking, woah, what if someone at Buffer reads about the small amount of time Toby is mentioning for stuff, what would they think?

I am hoping folks at Buffer do read it as I will be sharing it with them! There are some core values that Buffer has and one of them is to work smarter, not harder - I guess what I am trying to do this with post is work out the best way for me to work smarter!

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