Notes from a Floating Life Thoughts about productivity, digital living, and leading a simpler life

Achieving Your Goals Through Personal Bootstrapping

Someone writing on a whiteboard at a startup

You might have heard the term boostrapping bandied about. Usually, it’s spoken in relation to startups. The term comes from the phase Pulling yourself up by your bootstraps, meaning doing something on your own without any outside help.

When an entrepreneur bootstraps a company, they fund it themselves. They use their own money — savings, loans from friends and family, maxed-out credit cards, or the money they earn from side gigs — to start and keep the business afloat until it starts making money.

It’s an interesting concept. And you can apply the philosophy of bootstrapping to endeavours outside of business. You can apply that philosophy to what you’re trying to do or trying to learn, too.

Here are some thoughts about how to do personal bootstrapping.

Start By Scaling Back

We all have grand plans, we all have something that we want to do as quickly and as efficiently as possible. But if you have a limited amount of time to do something, you won’t achieve your goals as quickly as you want to.

Instead, scale back your expectations. Scale back your goals. Fit what you want to do into the time you have to do it each day.

Be realistic. And expect to slip every so often.

How do you scale back? You …


Think in terms of minimum viable product. Think in terms of what need to do to get:

  • Your idea up and running.
  • A solid grounding in what you’re trying to learn.

Take language learning, for example. When most people try to learn a language they start from the beginning and make a long slog to more advanced levels. Back in the 1980s, I knew a person who taught himself financial Japanese for his work. He could comfortably read and write around finance, and even talk and give short presentations on the subject. He couldn’t, however, have a more general conversation. At least, not at first. He eventually broadened his vocabulary, but that wasn’t his focus at the time.

Take what I call an A-B-C … N-O-P … approach — get a handle on the basics, then jump ahead to more advanced knowledge or topics. Or, put together a basic product, start selling it, then add to it gradually.

Set a time frame

And make that time frame reasonable. Don’t expect to be able to learn to program a custom shopping cart for your website with PHP in six hours. On the other hand, don’t spend more than an afternoon setting up your personal or business presence on the web.

How do you know how long something will take? It’s hard to estimate something you don’t know about. The best way to come up with an estimate is to ask someone who’s done something similar. Better yet, ask several someones. Then, average out the amount of time they tell you. Add 5% to 10% to the estimate just in case — the unexpected tends to happen and it will throw a wrench into your plans.

Think About What You Need

And then get it.

That could be books, software, courses, subscriptions. Anything that will help you reach your goal.

Remember that you’ll be spending your own money on those items. You need to ask yourself a few questions:

  • Do you really need all of it?
  • Are there cheaper or free alternatives?
  • Is there any way to defray the costs (like splitting them with someone else or buying used)?

Again, think minimum viable. Then, supplement what you have when (and only when) you need to.

Do the Work

You can do all the thinking and planning and scoping you want. But until you start working, and finish what you’ve started, all that thinking and planning and scoping is worthless. Ideas are cheap. Results, no matter how small, are what count.

And don’t discount small results. Take small, steady steps towards your goal. At each milestone, show your work.

You might only have 30 minutes a day to do the work, but those 30 minutes add up. They’re not like time you supposedly saved. You’ll actually see the results of those 30 minutes, and far sooner than you expect.

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