Catch-22s and Bootstrapping Your Life

Catch-22s are problems which have circular or paradoxical solutions. Named after Joseph Heller’s famous book by the same name, about a soldier who can avoid dangerous combat if he is insane (but applying for the provision is proof of sanity).

Many situations in life are close to Catch-22s, problems by which the method of solution which have the solution itself as a prerequisite. Building a successful business is considerably easier with access to capital and connections. Capital and connections are much easier to obtain if you’ve run a successful business.

Men who have had difficulty with women often lament that women claim to love genuine confidence, which comes from past experiences of success, which would seem to rely on having the confidence in the first place.

Of course, none of these are perfect Catch-22s. For every successful entrepreneur or relationship, there had to be a first success. A success that defied the circular logic that supports further successes. Overcoming these initial successes is hard, and worth studying since it may turn out to be more important than later, and grander successes, that we typically pay attention to.

Pulling Yourself Up By Your Bootstraps

Bootstrapping is another idiom that points to a seemingly circular situation. The concept, which means to achieve something using minimal resources, comes from an early 19th century American phrase to, “pull oneself over a fence by one’s bootstraps.”

Bootstrapping, that impossible of solutions, is the cure for that seemingly impossible of problems—the Catch-22s we all face in life.

The philosophy of bootstrapping is popular in entrepreneurship circles. The idea of building a company with initially limited resources is a powerful one. While many businesses required enormous investment to make viable—many haven’t. I spent about a hundred dollars to get this website started. Every month since, the business has paid for itself.

Bootstrapping isn’t a preference, it’s often a necessity. I don’t frown on entrepreneurs who invest large amounts of money in a project before it returns profit. Sometimes that is a smarter strategy than being stingy. But I started my first attempt at entrepreneurship in a small-town, with no connections at fifteen. I had to save for college and all I had was the part-time income of working as a lifeguard.

Bootstrapping applies to life, not just business. It’s the skills necessary to build something with zero resources or, seemingly, any of the prerequisites for success. Habits, discipline, social skills, confidence and competence are all, to a certain extent, driven by these exponential forces which make it easier to continue than to start.

Studying Small Beginnings

Often the advice that matters at one stage becomes irrelevant at another. As a blogger now, I don’t chase for links. I know that enough people read my blog that, if my content is good, it will spread. Spamming my articles to other blogs isn’t a good use of my time, and may even be a detrimental force since it doesn’t allow people to discover it organically.

But when I started I had zero traffic. If I didn’t tell people about what I was writing, nobody would read it. My early method was to track down blogs that frequently linked to articles similar to mine—and give them a friendly heads-up whenever I wrote an article.

The concept of marginal benefit comes into play. The marginal benefit of telling someone about your article when you have zero traffic can be quite high. Now I’ve found that same marginal benefit is often low, or sometimes even negative. It makes far more sense to build strong relationships with other bloggers before finding ways to share traffic. That has a high marginal benefit, but such opportunities are often unavailable to new bloggers.

Because the marginal costs and benefits are very different in an early phase than in a mature phase of growth, it doesn’t make sense to copy the methods of someone far along in their development. Study small beginnings, not only grandiose middles.

Bootstrapping Life

Career and entrepreneurial activities have an obvious bootstrapping component. This is often why they experience exponential growth over some range of their progress—the effects create the causes resulting in a compounding effect.

Other areas of life have less pronounced Catch-22s as well. Consider self-discipline. Self-discipline is trained through exercising self-discipline. The positive reinforcement of succeeding at discipline-requiring tasks strengthens that resource. However, it’s much easier to succeed at them when you already possess discipline in the first place.

I found something similar in my early attempts at habit formation. I was so used to being lazy and giving up at everything, that it was hard to even get the early successes I needed to reinforce those behaviors. I failed a lot at simple challenges because my self-discipline muscles were weak.

Is it Bootstrapping or Immutable Character?

I used to look at the feats of the people I admired and feel inadequate. How could they start companies, have adventures and succeed across so many areas of life when I failed at so many. They persevered through difficulty, and I gave up.

I wish someone had told me that those character traits are often bootstrapped as well. Discipline, courage, charisma and all the ingredients of success are manufactured. Even if you don’t feel you possess them now, you can generate the experiences you need to have them in the future.

Scientists who measure personality traits notice consistency over time. While I don’t doubt that our genes play significant roles in our development, part of me wonders whether those traits are truly unchangeable or whether their apparent persistence is due to the Catch-22 required. Divergence from a different starting point is not because change is impossible, but because it requires bootstrapping. Bootstrapping is arduous, so when examining populations we see most people flowing down the stream they were cast into, not swimming into a new one.

Swimming upstream is hard. But, if you work at it, eventually that upstream swim becomes downstream and what was improbable becomes inevitable.

  • Shrutarshi Basu

    It’s interesting that you talk about self-discipline and habit formation as examples of bootstrapping — those are two areas I’m struggling with in daily life. As someone trying to bootstrap my self-discipline, do you have suggestions for how one could go about getting started?

  • Umar

    Training your willpower/self-discipline is simple.
    Just do it stage by stage.
    Try quitting television, alcohol, partying, masturbation, porn, music, wasting time etc.

  • maga

    i once came across the quote “we are what we repeatedly do” [by Aristotle?]. when i think about it, it becomes probably the best advice on breaking habits and patterns in life i’ve ever found. instead of trying to change yourself, which at least for me is a difficult concept, just do what you think you would be doing if you were already some kind of a better version of yourself.
    i also agree one can work on the personality traits. i don’t think anyone was born truly outgoing, tactfull negociator with professional knowledge. we all grow up and acquire new skills. the growing up never stops in my opinion so it seems irrational to me when a 20-something person says they are too shy/uncharismatic/untalented/lacking to do something, as it they were already “done” changing and evolving.
    thank you scott for an inspiring post. it was good to remind myself to stop whining and step beyond my comfort zone.

  • Martin

    Hi. This article catch my attention. Too bad, my first language is not english, and I struggle to understand the main concept behind “bootstrap”, as because I’m an IT guy, the only concept or meaning I ever understand in english about bootstrap is OS bootstrap in computer, which starts at the beginning phase in the computer booting. So what? Do you mean that I have to bootstrap is that I have to force myself to start something even with a very limited resource? To “just walk with faith” and learn all the things I still don’t know of along the way? A little clarification of what exactly you meant with bootstrap or what to do in bootstrap phase will be very appreciated, as I really see many of the catch-22 instance in my life. Thanks. 🙂

  • Glauber

    Umar, I don’t think self-discipline is not doing anything you like. One should allow himself to relax when it’s the suitable time.

  • Daniel DiPiazza

    I like the idea that traits previously assumed to be “hard-wired” are often curated. How do you gain more charisma? Act more charismatic — and intentionally create a positive feedback system of increasing returns.

    Definitely valuable advice. Thanks for this, Scott!


  • bunyonb

    I don’t think I am ready for this……..honestly…I have to do things at my own pace to prevent myself from going crazy..

  • ferg

    Hi Martin
    May I refer you to the section on Bootstrapping in this article from where the concept might be offered some understanding for you , me both

    Pulling Yourself Up By Your Bootstraps
    Bootstrapping is another idiom that points to a seemingly circular situation. The concept, which means to achieve something using minimal resources, comes from an early 19th century American phrase to, “pull oneself over a fence by one’s bootstraps.”
    Bootstrapping, that impossible of solutions, is the cure for that seemingly impossible of problems—the Catch-22s we all face in life.

    I seem to remember my Dad explaining this one to me when he was busily working at instilling within me character, He described it as a time when one may be down to the extreme (A Soldier on the battle field, having to get up and carry on fighting for life despite the most grave of circumstances)

    Hope this helps

  • Keri Peardon

    I like the idea that discipline is a “muscle” that gets stronger as it’s exercised. Of course, the exercise is hard, but at least it’s not an impossible task–it’s not something you are either born with or without.

    I also like to hear that you were once a slacker, too, Scott. It makes me hopeful that I might one day whip myself into shape, too.

  • Keri Peardon


    Bootstraps are, literally, tabs or loops inside a tall boot (like a riding boot) which give you something to hold onto while you are pulling the boot on.

    Have you ever seen a cartoon where Bugs Bunny picks himself up by his own ears and just hovers in the air?

    To pick yourself up by the bootstraps means to lift yourself up off the ground like Bugs Bunny picking himself up by the ears.

    Of course that’s physically impossible, but that’s the point: the metaphor means to do something that’s seemingly impossible with no outside assistance.

    For instance, Andrew Carnegie was born to a weaver in a lower-middle class household in Scotland. He came to the United States while he was a teenager, and began working. He was very intelligent and took calculated risks with his jobs and attracted the attention of bosses who appreciated his initiative and promoted him. Eventually, he became one of the wealthiest and most influential men in the world.

    We would say that he pulled himself up by the bootstraps because being born where and when he was, in the social class that he was, it should have been almost impossible for him to rise as far as he did. But through his tenacity, intelligence, and hard work, he made the impossible possible.

  • Matvei

    Great post. It’s always comforting to know successful people were not born this way.

  • Eric-Wubbo

    Scott, nice blog! Made me make notes for later use, which few posts do.
    For me the core would simply be that bootstrapping involves first doing small/easy stuff, to get experience, and celebrate the victories. For example, if you’d want to bootstrap confidence with women, you would not start to chat-up a 20-year-old supermodel but try your luck with a less attractive woman instead at first. Besides, bootstrapping is not only about confidence, you also need time to build genuine skills.

    I would however _never_ try to bootstrap self-discipline. In the case of scientists, my ‘speciality’, mediocre scientists tried to rely on self-discipline, great scientists did not. This is because if you’re not motivated to do something, you should not try to override such data that your brain is giving you [hey- this activity does not seem worthwhile] by ‘self-discipline’. After all, the activity may indeed not be worthwhile, for example. You should find out if your project is really motivating you, and either switch or change projects or seek ways to increase motivation (seek social support, celebrate small successes, set small challenges/contests for yourself). If you want to enhance self-discipline, I think you should first analyze the problem you’re struggling with instead.

  • Juan

    The points presented on this post are simple yet awesome. I especially appreciate the connections Scott makes between the concepts of Catch-22, Bootstrapping, success in one’s life and business. It was a very eye-opening article and my biggest takeaway is to just do it, no matter how hard it seems or how much work it takes.
    Thanks also to Keri Peardon for her comment. Her explanation of Bootstrapping by comparing it to one of Bugs Bunny’s acts is ingenious. Also I had never heard of Andrew Carnegie origins so that was also a gem.

  • Keri Peardon


    If you’re interested in Andrew Carnegie, you can find his autobiography online for free. (I can’t remember if I got it from Google Ebooks or Project Gutenberg.)

  • Baggio Wong

    @maga Love what you said…this is a very useful technique – there’s an element of positive reinforcement on this…really powerful, will remember when trying to apply change in the future!


  • Pradnya

    All I could think about was Bootstraps’ bootstraps…but in a positive image…literally pulling oneself up by one’s bootstraps. Hearing that is inspiring…and inspired me to write my first comment…something I’ve been refraining from due to fear of getting started…and backlash

  • Tony Pierre

    There is often little or no alternative to bootstrapping for many would-be entrepreneurs. Some folks stumble their way through bootstrapping, catch-22s self-discipline and hard work with the ultimate goal of success as their primary motivator.

  • Sammy

    Quite enlightening post. while we understand the psychology behind change and improvement of habit, its very important to consider the fact that there is a creator who specializes in changing life.
    Obviously, habits like that of smoking,poor sexual related habits, etc. defy applied psychology (even bootstrapping efforts fail). miracles are part of nature if you believe in God. some of these need the experience called miracle. so do sincerely call on God and he will do it.
    As Christians around the world celebrate his death and resurrection I wish you readers and writer- Scott, greater victory in life, in Jesus name. Amen.

  • Ethelred

    @ Keri

    Thanks for the explanation of “bootstraps” Keri 🙂
    I now have a very clear image of what it means (English isn’t my mother tongue).

    Comparing discipline with a muscle that you train is a good idea as well.
    I’d say that it takes will and courage to stick to discipline, and I believe those can be trained and improved too.
    Practice, practice, practice.

    The good news is that once you’ve harvested the first results, as hard as it may be at the start, it is so gratifying that you can hardly give up!

  • Andrea

    Love what you had to say on marginal beinifit! I had one of my project managers send you an email. Hope we can connect! Great post!

  • Angela Wuerz

    I really liked your blog – I’ve just finished a meditation challenge for 21 days, changing habits takes a lot of energy at first. It becomes easier over time until you don’t even think about it anymore. You just do it!
    Just like your comparison about the swimming upstream!

  • KC St.

    Umar said, “Training your willpower/self-discipline is simple.” Obviously Umar has a VERY different brain than I have. In my experience there is nothing HARDER to do that be self-disciplined. I have found impossible to perfectly keep a 30 day challenge. Typically these kinds of things are so discourage that I don’t even try them anymore.

    I am interested in many of the suggestion on this blog, but have found that they are not written for my type of brain. I think you have to have a brain that naturally likes routines and is very driven and goal oriented and practically OCD. I’m more on the ADD end of the spectrum. It just doesn’t happen for me.