Why bootstrappers should track their time

The Problem

Most people only track their time when they are billing by the hour, and most people aren’t billing by the hour. As a result, most people don’t track their time.

Now, you can try to bootstrap a new business or product without time tracking, but you’re doing yourself a great disservice if you do. The problem is that we always think we can get more done than we really have time for, and we inevitably think we’ll have more time to work on things than we really do. Add to this the fact that humans are incredibly bad about judging and estimating time, and it’s pretty much guaranteed that our after-hours projects will take longer than we thought.

One of the biggest consequences of this to someone trying to bootstrap a new company, is an overestimation of what should be included in your Minimum Viable Product. There are so many features that would “be easy to add” or take “no time at all”, and even when they are easy, or fast, most of us are lucky to even have enough time to get the truly core functionality done. Not having a good grasp of just how long things are taking to complete allows these “nice-to-haves” to sneak in when they should really be held back for a future version of the product.

With no reliable information on how long it takes you to do something you can’t create useful estimations. When you overestimate your capabilities you underestimate the value of outsourcing, and what things most need to be outsourced.

In the end, bootstrapped projects, worked on in stolen hours between “real work”, and life, move at an almost glacial pace. Time tracking is the only significant tool we have to address this, and it becomes increasingly more valuable with each successive project.

##The Techniques

Precision is not important. You’re not billing anyone for this. What is important is that you’re keeping good track of the time spent on specific types of tasks, and that you can easily go back and see how much you spent on each. The most important thing you can do is to choose a tool that makes it easy for yourself.

Paper tracking can work, but the ability to see a nice graph of the time you’ve spent working over the past week should not be underestimated either. Seeing an unbroken graph showing your constant forward progress can really help keep you moving forward, knowing that you will make it there. If you find yourself skipping more days than you really ought to, that graph will help you to quantify just how much of a slacker you’ve been, and hopefully kick your butt back into motion.

My recommendation is to go with task groupings that are relatively high level, but detailed enough to help you assess where your time is going in a useful manner. Using just “Design” and “Coding” isn’t going to cut it. On the other hand, getting too detailed is going to be annoying to set up, frustrating to choose between when entering new time, and harder to track usefully when looking back.

These are the task types I’m currently tracking for my web applications:

  • Coding
  • Web Design ( HTML / CSS work )
  • Graphics ( logo design, image creation, etc )
  • Marketing
  • Market research
  • Code Research (tool research, project specific technique research, etc.)
  • Contractor evaluation / management

Track everything.

If you have to read a book to learn something specific to your product or it’s market then track it as research. These hours add up, and we never realize just how much time they take. Worse, we don’t take it into account when we’re trying to figure out how much time the next project is going to take. Track your time on this project and you’ll have some basis for your future estimations.

When outsourcing small focused task like logo design you’ll frequently be billed for the hours worked, but there’s no point in trying to convince the contractor to learn and use your time tracking system for your short task. Instead just enter the hours they spent working on it into your system yourself. If they’ve quoted you a flat rate, then just ask them for an estimate of how long it took when everything is done, or at the end of weekly updates.

In my case the Graphics, Marketing, and some of the Market Research is outsourced, and I’ll typically just add in the amount of time it took them in single shots on the given week. It makes the graphs look funny but I don’t really care how much they worked on any given day. I just want to be able to keep track of how much time they can and do devote to the project so that I can better predict what’s going to happen the next time I hire them.


Keep an eye on your hours through the week. Working a specific number of hours each day rarely works when you’re a bootstrapper; your day job, personal responsibilities, and taking time to relax and stay sane rarely leave us with much for our side projects. So, don’t berate yourself if you only got half an hour in last Tuesday. Use it as a tool to keep yourself moving moving forwards, and head-off slacking before it becomes a problem.

As your project goes forward patterns will start to emerge. You’ll discover that some types of tasks are taking you notably longer than expected. When you see this, don’t just sit on the information. Use it to your advantage. Outsource the parts that aren’t your core competencies. It’s generally a good idea to do that anyway, but being humans filled with ego, we tend to think we can do it all. Use what your time tracking is telling you to help convince yourself to get help. Remember, every additional day you have to spend working to get your project out the door is another day it can’t be making you money.


At the end of a project make a writeup for yourself with all the important takeaways, including how much time each part of the project took. Then, figure out how much it would have cost you to outsource each ofnthe parts. Don’t calculate it at your rate, calculate it at the average rate of the freelancers you could have hired to do it for you. When outsourcing to people in foreign countries this can be significantly cheaper.

Once you’ve done that, figure out how fast your could have gotten the project done if you had of oursourced and parralellized as much of the process as possible. Some things simply have to wait for others to finish, but some tasks, like putting together your marketing strategy and copy can be worked on almost completely independently of other tasks.

##The Tools As I said above, the most important thing you can do is to choose a tool that makes it easy for yourself. Some tools have incredible lists of features; there are only two that matter.

  1. How easy is it to enter time? More critically, how easy is it to enter time when you discover you forgot to hit start ontheir handy-dandy stopwatch.
  2. How much do you like the tool?

Some tools have great functionality, and designs that are so ugly as to make you cringe every time you open it. Don’t use them. The harder, or less pleasant a tool is to use the less likely you will be to use it, especially when you don’t “need” to be using one.

My advice is this: almost all of the tools out there offer either a free plan or a 30 day trial. Pick the first one that looks interesting and isn’t too expensive for you. Use it religiously for one week. If it annoys you, or doesn’t make you happy, close your account and move on. Don’t bother re-entering the past week’s data. Repeat until you’ve found something that works for you. Do not let yourself just accept it as “good enough” and abandon the search. Humans are terrible about this. We’ll almost always stay in a slightly uncomfortable situation instead of risking a change that could make things better. If you’re not happy with your first choice, force yourself to try something else.

What I look for:

  • Good design
  • Trivially easy data entry. Everyone offers some kind of easy stopwatch tool. Few apps make it trivial to enter time without that.
  • Support for lots of projects in a plan I can afford. I am usually only working on one project at a time, but have an ongoing stream of them and don’t want to have to throw out the data I’ve collected on old projects in order to start a new one. The more historical data I have available the better I can plan my upcoming projects.
  • Good graphing tools that let me easily see the overall time spent as well as the time spent on given task types.

Things to watch out for

If you’re going to be outsourcing make sure that the tool has support for enough people at a price you can afford.

Many of the tools out there are very focused on freelancers, and small businesses that bill by the hour. They have the basic assumption that if you’re tracking your time, you must be billing for it, and if you’re billing for it then their software has become a critical piece of you making money. It’s a reasonable, and fair assumption and they should be compensated accordingly, but when you’re using their software to simply work on better managing your time, many of the features they’re offering become irrelevant, and not worth the money.

Some tools only retain your data for a limited number of years. This may or may not be an issue, but it is something you’ll want to consider. Personally I’d rather not have to worry about what to do to store all my old data on a rolling basis starting 3 years from now (or whatever their cutoff is). When I find a tool I’m happy with I want to be able to just stick with it and not have to ever deal with tracking down a new provider or archiving old data myself.

Pie charts. Seriously. The human brain is simply incapable of accurately judging the relative size of pie slices. Pie charts are only useful to show massive disparities. When evaluating the graphing tools of an app pretend their pie charts don’t even exist, because the data they provide you will not be notably useful.

Which tools to choose?

I wish I had a handful of great tools to point you to. Unfortunately I haven’t found anything that really makes me happy. I’ll let you know when I do. The best place to start though is Wikipedia, which has a great Comparison of time tracking software.

Have you found a time tracking tool that would be great for bootstrappers? Let me know.