Productivity Challenges of a Flexible Lifestyle

I was invited to speak at a webinar by the Estonian e-Residency team. I spoke about productivity challenges specific to those with a flexible lifestyle — like the digital nomads that utilize e-Residency to form their companies. Though in 2020, the advice is also relevant to those with (what are normally) traditional jobs.

Below is a written version of that talk. I’ve skipped the self-introduction and background story on starting my company. However, if that interests you, you can read that here.

Productivity = Organization + Psychology

There are so many different systems and tools. But it’s important not to try to force yourself into a system, rather to find one that matches your lifestyle. You may or may not have the problem that any particular system or “tip” is trying to fix.

When you have a lot of autonomy and few boundaries in your life, you face different productivity challenges than the “typical” person in a traditional job. So I’ll go over what I think are the biggest ones. Hopefully listening to me articulate these challenges will in itself give you some awareness that helps you avoid pitfalls.

I’ll also go over a solution for each problem I cover. Not just apps and tips, but a way to approach that challenge so you’re not just depending on will power.

But speaking of apps! This is where I plug my software, if what you hear today resonates, then try Simply Goals & Tasks. I designed it for myself. And assuming you are (or aspire to) be a business owner as well, then I would say it deserves to be on your list of things to try. But it’s a really personal thing, I’m not going to talk about tools too much.

Problem: Organization

Keep things together that should be together.
Keep things apart that should be apart.

If you’re actually losing track of what you need to do, or you have a work space full of things that distract you, then organization is your problem.

And there is actually a golden standard here: “Getting Things Done” by David Allen.

It’s a book. Or according to their website, it’s a “Movement”, ha! I’ll point you all to the wikipedia page where there is a 2-page summary. Here you’ll get the idea and can follow up on the parts that interest you most.

Moving on…

You probably know what you need to do to be more organized or improve your business, but you struggle to actually do it. So I’ll move on to, what I think are, the more interesting and more psychology focused productivity challenges

Problem: Not enough hours in the day

When I was getting ready to quit, I kept fantasizing about how I was going to have so much time for cooking and exercising and all my other hobbies. It somehow never occurred to me that you don’t actually get any more time when you work for yourself.

True: you save time on commuting. You have less overhead. But now you have to also run a business besides doing whatever it is you do to provide value to those who pay you. And probably learn a lot, too, when you’re getting started.

So, you’re still working full-time. Where would any extra time come from? Basically, there isn’t any. Unless you are going to work part-time. Which I don’t recommend at the start, it would be too easy to accidentally work 0 hours. Start full-time and when you’re established, cut your hours.

Solution: Decide how you want to spend your time

This is pretty easy. We can do an exercise. I have a link. Here, I made a spreadsheet.

You’re going to decide how you want to spend the 24hrs you get each day (168 each week). The same as you would dollars in a budget. Doing this on paper (or a spreadsheet) you are almost certainly going to have some epiphanies in the process.

For example, I kept beating myself up for not spending more time on my photography. I did this exercise, and I realized I was actually spending more time than I ideally wanted to spend on that particular hobby.

Knowing this meant (1) I could stop feeling bad about a failure that wasn’t actually a failure. (2) Also, I started spending less time on that and had more time for my real top priority: my work.

So let’s look at that spreadsheet together. You’ll need to make your own copy.

Exercise 1: (First tab in the spreadsheet)

1) List out all the things you want to spend time on, as well as things you need to spend time on like sleeping and eating. I’ve filled in some examples for inspiration, you should change those.

2) Then how much time you want to spend on each one. You change the black weekly number. The grey numbers are being auto calculated from the weekly number to make the hours easier to understand.

Don’t forget down time. No one can be “on” all the time. You need some blank “nothing” time. When you’re deciding how much “nothing” time to include, consider if socializing, social media, or other sudo-productive activities will be included here or if you’ll count those separately.

Does it add up to less than 168?

Almost certainly not. I would actually save this initial version as a memento of how you’ve been beating yourself up for failing to accomplish literally impossible goals.

3) Now go back and take time away from things. Get down to under 168.

And this is your Ideal week. Lots of times (most the time) it won’t be perfect like that. But now you at least know what a perfect week looks like. And, more importantly, you have probably adjusted your expectations for your goals, like how I did with photography.

Exercise 2: What does an ideal day look like where you’re on track to meet those weekly goals?

The point of this exercise is just to have in your mind what an ideal day looks like so you can try to make your days match that template as often as possible. Also, you might catch something you forgot to include in your weekly “budget”. If you used up all 168 but didn’t remember showering, well you gotta go back and make some more cuts.

This is exercise in on the same spreadsheet link, it’s just a tab on the bottom. Or you can write it out free hand: write what time you wake up, getting ready, all the way to going to sleep. I redo this exercise all the time just in my journal. Especially this year with things changing so much; I’m continually redefining what a perfect day even means.

Problem: Flexible Time feels like more time than structured time does.

Have you noticed how if you have 8hrs strictly booked, it feels like you don’t have a minute to spare, but if you have a more nebulous 8-hrs of work to do, it feels like you do have extra time?

I’ve come up with two reasons I think this is:

  1. first is that we overestimate our abilities (this is the next section) and
  2. the second is that it becomes too much for our minds to keep track of.

Rather than a day, let’s expand the example to a week.

I especially felt this when I was freelancing. Each week I would have (easily!) a week’s worth of things that really should be done by Friday. However none of it absolutely needed to be done today. In that situation it felt impossible to motivate myself to buckle down to work.

Now. It sounds like I’m advocating for structure. The opposite is actually true.

I personally don’t want to give up my flexibility, that’s the whole point of this lifestyle!

So much productivity advice is about forcing the rigidness of a traditional job and lifestyle into a life with total autonomy — but why do that! Just get a traditional job at that point. We chose this life because we want it.

Solution: Flexible Scheduling

(This is going to get a little technical)

Keep things flexible long-term, but schedule to-the-hour in the short-term.

Keeping things flexible in the long term matches reality. When you schedule a task (not to be confused with an appointment) for an exact date and time more than a week away, be honest, you’re going to end up rescheduling that. It’s really just serving as a reminder.

But all that rescheduling has negative consequences:

  1. It’s lost time on overhead.
  2. It’s demoralizing because it can feel like a failure when you end up (justifiably) doing something else more urgent and important during that time you arbitrarily picked a week earlier.
  3. And finally, all that random scheduling means that you don’t have a true agenda you can look at and know when you are busy and when you are free.

These are big problems and it’s why I don’t recommend using a Calendar for your tasks.

If something has to be done just “next week”, don’t arbitrarily pick a specific day until you are planning next week and at that point the day you pick isn’t arbitrary anymore. When you schedule something for a specific day, there has to be a reason that day is the best for that task. Even if that reason is as simple as, “I’m already book solid the other days”.

Then follow through. You only reschedule if something actually changes, never because you just don’t feel like it.

Tooling to do this:

This is the way tasks should be scheduled. It’s the way paper planners work (and a paper planner is a great option) but if you want something digital, you oddly don’t have a ton of options.

  • There’s Simply Goals & Tasks. As far as I know, is only to do list app that can schedule tasks at different levels of granularity like month, week, day, and time.
  • Make your own kanban (aka trello) board. I recommend xenkit over trello.
  • A word document or spreadsheet that you make yourself.

Bonus: if you figure this one out, tracking your tasks and scheduling them in a way to maximize flexibility as well as accountability: you will be so organized! I mean, like, finishing you Christmas shopping in November level organized. This one is a really big win.

Problem: You don’t even know if you are over booked or have time to relax

This one overlaps with the last point and has the same solution: you need an agenda you can trust as accurate. That’s not full of arbitrarily scheduled tasks that don’t actually need to be (and probably won’t be) done the time they’re written.

How to know if you have this problem? If you don’t know the answer off the top of your head to the following questions, then you have this problem:

  • Do you know how many hours of work you’re already committed to this week?
  • Do you know if you can get it done easily or if you’ll need to work late a few days?
  • If a good opportunity fell in your lap right now, could you accept?

It’s really hard to know those answers when you’re tracking all 168 hours of the week mentally. With a traditional job, work is work, and you’re just mentally tracking weekends and 2hrs each weekday evening.

If you can’t answer those questions then you will always either:

  1. Put off too much until the last minute, then either fail or kill yourself to finish or
  2. On the flip side, you will always be working. Even when you have time to relax you won’t enjoy it because you don’t realize. You might be professionally successful that way, but that’s no way to live.

Figure this out and you’ll be more motivated on Mondays or in the mornings when it feels like you still have so much more time, but actually have just the right amount of time. Mastering this will also help if you’re having trouble disconnecting and relaxing.

Problem: Unrealistic expectations for your future self

We all have this mental version of ourselves at our most energetic and productive. And we think we’ll be able to call on that version of ourselves “later” even when faced with the evidence of not being able to call on that self right now.


Step 1: Accept it. If you’re an adult, that means you (presumably) have less energy than you did 5yrs ago. Sorry.

For me, I really can’t count on my best self, because I have 2 small kids, and I’m always tired. So I now start things insanely early to compensate.

Step 2: Be nicer to your future self. This is a cool trick. Think of future-you as a different person and treat them with the kindness that you would treat a friend. I’ve been practicing this one and it brings an odd joy when I make a little sacrifice to make future-me’s life easier.

Last one…

Problem: Knowing yourself and your moods

Knowing yourself is the biggest thing you can do to improve your productivity. But unfortunately it’s the shortest part of my talk because, obviously, it’s so different for every person.


All I can really do is rattle off some tips:

  • Pay attention to yourself, your feelings, your moods, your energy level.
  • When you are down: What caused that? What’s making it better or worse? When you get out of that funk, how did you pull yourself back up?
  • On the flip side, When you’re on a roll, take a moment to look around at what’s working so well so you can keep those things in place.
  • What tasks do you always put off? Could you permanently delegate them, or invent a solution to force yourself to get it over with quickly? Because you waste time and hurt your morale when you keep procrastinating.
  • Making regular time for meditation or stream-of-consciousness journaling where you work out your thoughts on the things above.

Personal example: if I’m burning out, I now know to stay away from TV because it pulls me down further. Instead, I read YA fantasy that’s just as much a break and escape, but it doesn’t have that same effect as TV.

It takes time to learn your own patterns, but it’s worth the effort. This self awareness will improve your productivity as well as any type of self improvement.


We talked about:

  • Organization
  • Not enough hours in the day. Solution: making a conscious decisions on how you want to “spend” the hours you have.
  • Flexible time feeling like more time than it is. Solution: don’t arbitrarily schedule tasks, get a system where you can keep things general in the long-term and get specific in the short-term.
  • You don’t even know if you are over booked or have time to relax. Solution: Same as the previous: get an agenda you can trust as accurate.
  • Too high expectations for your future self. Solution: accept reality, plan ahead, and be nice to future you.
  • Knowing yourself and your moods. Solution: self reflection.

Categories: ideastalk