How To Organize Yourself as a Solo Founder

The solo founder is not a role for the faint of heart. In the dark days of an early-stage startup, despite the sun being out, the sky looks dark and pale and gloomy. The best-case scenario is that you have a support system cheering you on. However, the person doing the heavy-lifting is still you.

There are so many things to go wrong, so many challenges to take on and keep track of. Without a system, failure may come sooner than expected¹. There are plethora of “productivity” systems out there. Everything from “Eat the Frog” to “Manager’s Schedule, Maker’s Schedule” and anything in-between. In my experience, only one system stands above the rest; in the mountain range of productivity systems, the mountain of GTD is the highest peak.

GTD or Getting Things Done² is a system with a few key principles discovered by David Allen in his twenty-year plus consulting career. These principles are devoid of tools, so rest assured, you can use whatever tools you like³. The principles are the following:

1. Your mind is a great place for having ideas and a terrible place for keeping them.
2. A good system with complete trust is better than a perfect system with no trust.
3. Deciding what to work on at any given moment comes down to energy and feeling.
4. From chaos comes staleness, and staleness causes irrelevance.

I would add that only the first principle of the four is mentioned verbatim by David Allen. The rest are distilled by yours truly, after reading Getting Things Done and watching several of David’s talks.

Is the mind really a terrible place for keeping ideas?

There is a Chinese proverb: “The faintest ink is better than the best memory.” How often have you gone to the grocery store intending to buy toothpaste and returned with everything but toothpaste? And how often have you made a grocery list and felt a) that you accomplished something and b) that you got everything? In my case, always. This principle of capturing your thoughts extends to everything. With the GTD methodology, this is the first step; getting everything out of your mind and putting it somewhere. Imagine if you had a giant to-do list of everything you ever had to do. What would that look like?

Try it out now. Take a piece of paper or fire up your favourite editor and create a list of everything on your mind: The things you have to buy to the things you have to do at work. If you are out of ideas five minutes after creating this list, look around your house, and more things to capture will pop up⁴.

Typically, when people create a list, they feel relieved and sometimes overwhelmed. That’s ok. If the unknown is uncertain and scary, what you have in front of you is known and less scary because it’s easier to do something about (more on doing later).

As a solo founder, I had many things I needed to keep track of and remember. I also had other responsibilities outside of my startup. For instance, I had to get an oil change and this was work too.

The more often you do this, the sooner you realize the strength of the principle. By simply capturing your ideas, you are more in control than ever before. Picture yourself in a situation where something is happening, and the phrase “Oh sure, I’ll look into that” or “That reminds me, I should do that” comes up. Whip out your trusty notebook and write it down.

A Good System

Imagine every time you went to turn on your car; it only started sometimes. Would you trust your car when you had to travel? Probably not. Any good system needs to be one that you can rely on and trust. If the system you are working with is out-of-date or doesn’t have the functions you need, you won’t use it anymore⁵.

This is why a single source of truth is important. It may be tedious to start however, it pays enormous dividends in the future. The primary benefit is the confidence you feel when what you see in your single list is mostly all there is. Have you only managed to capture 80% of everything you must do? It’s still better than having it spread out on multiple lists that you must reference.

Now, maybe you hesitate when you realize your list has over two hundred items. Worry not. This is where projects and the two-minute rule come into play. These will be key components of your system. If there is something on your list you can complete in less than two minutes, then do it now. If it has more than one step, then it’s a project.

As you categorize your list, it will become smaller and more manageable. Remember our second principle; a good system with perfect trust is better than a perfect system with no trust. In other words, spend less time making things look nice and spend more time building a habit to use for your single source of truth.

To build a reliable system, it must be an up-to-date system. One of the reasons GTD fails for many people is the fourth principle. Our daily lives are chaotic, and there are 101 things to remember and do. Your source of truth will need to change to reflect that so it doesn’t go stale. When looking at your list, if you notice some things are very old and some new things are not added, your list has gone stale. It’s time to do a review.

How to make sure your system doesn’t go stale

The review process in your system ensures your source truth remains exactly that, truth. During your review, take time to remove things that are not relevant such as small TODOs or projects you’re not interested in anymore⁶.

This is also the perfect time to check your archives to see if there are projects you want to resurrect. Many times during my startup, I had to archive a project due to a lack of time or resources. However, as I did my weekly review, I checked my archives and re-evaluated these projects. Was there a project for which I had resources now? Was there a project which aligned with my goals? This was a tremendously valuable exercise, allowing me to freely archive projects with confidence, knowing I would be able to revisit them when the time was right.

By doing this review now and again⁷, your system stays up-to-date, and this builds trust. The single biggest block to adopting any system for the long term is reliability. Will the system work day in and day out? The amount of time you spend making sure your system is reliable will pay massive dividends. At first, it might seem like a chore, and the first couple of times you do your review, it will be fairly boring — I’ll admit that. However, once you do it 3, 4, 5 times, you won’t be able to live without it.

What should I be working on?

David Allen recommends that you go with your gut⁸. For whatever reason, given a list of things that need working on, you will have a pretty decent idea of what you should be doing. Of course, this is not always the case, and for that, he recommends:

1. Context
2. Time available
3. Energy available
4. Priority

These four criteria are practical and easy to remember. There isn’t some weird formula that you must apply or create to figure out what you need to do at the moment. Let’s say you are on a crowded train with twenty minutes to your next stop, and you only have your phone. What do you do?

Pull out your almighty list and determine what is appropriate for that context, given that you have twenty minutes. Maybe this is the best time to respond to a couple of emails or text a friend or watch a YouTube video. Sometimes we feel guilty about what we are doing. There’s a voice saying, “You could be doing something more productive.” By using the energy and feeling criteria, you don’t have to feel guilty. There will be times you just don’t have the energy to work on anything of substance. That’s ok. Once you recognize you don’t have the energy or the context isn’t right, you can find something for your present energy level that lets you still make progress.

What tool should I use?

This is the least important question, but most often it’s the first one we focus on. Tools come and go (who remembers Lotus Notes?), but principles stay. Instead of recommending a specific tool, here are some criteria to look for when selecting a tool.

1. Does the tool work on mobile?
2. Can you create a detailed view and a big-picture view of your projects?
3. Are you able to move items from one view to another?
4. For example, are you able to archive a project easily?
5. Are you able to add tags and filter them?

Pick your favourite tool and determine if it can do the above. Or, with adjustments, can it be made to do those things. My tool of choice is Emacs with org-mode.

Emacs is an editor which allows itself to be modified. In the same way that a blacksmith makes her tools, Emacs lets the user create tools to use within Emacs if they choose. Org-mode is an “application” inside of Emacs⁹ which lets you store lists (among other things) and operate on them with shortcuts.

There are plenty of guides for using GTD with other tools like Todoist, OneNote, Outlook and more. Irrespective of which tool you choose, make sure it’s one you are comfortable with and can see yourself using in all kinds of scenarios. Furthermore, remember the principles are far more important than the tool. If you find a tool that satisfies 80% of your requirements, then use it. Less time spent fiddling with your chosen tool gives you more time to spend capturing, clarifying and determining your next steps.

You don’t have to be a start-up founder to reap the benefits of GTD. Once you have mastered the basic concepts and chosen your favorite tool, you will see for yourself how effectively the system can work. And the brilliance of GTD is that it becomes more beneficial as you become more proficient in its use.

Footnotes

[1]: This is not to imply all solo founders fail, simply that the odds are stacked against them.

[2]: This is an accurate name but a terrible one. It reeks of productivity gurus with vision statements and pie-in-the-sky thinking when it is the exact opposite.

[3]: A better tool won’t make you more productive; any more than a better paintbrush will make you a better painter.

[4]: If you notice a leaky faucet while walking around the house, put that on your list too.

[5]: Most people’s solution to this is to have many lists. The inevitable happens when one list with something important on it is misplaced. You then lose trust in all of your lists.

[6]: If you are worried that you might want to reactivate a project in the future, do not worry. Just archive that project. In other words, put it on a list called “someday/maybe” and refer back to it from time to time to see if anything is interesting in there for you to reactivate. This is similar to having two trash cans. The first is soft trash, which you can go through in case you throw out something important. The second is the shredder. Once something goes in there, that’s it.

[7]: For me, this happens about every seven days. For some, it might be shorter, and for others, it might be longer.

[8]: David Allen, Getting Things Done, 205

[9]: Those familiar with org-mode and Emacs will cringe at this description but bear with me. For the reader completely unfamiliar with either, it’s pointless to describe major/minor modes and Lisp. The motivated reader should read about Lisp (the language which allows you to modify Emacs) and major/minor modes to fully grasp the power of Emacs

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