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.
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.