You Need a Bit of Pessimism

You know, sometimes it might make sense to see the glass as half-empty.

I don’t recall exactly who said it — feel free to chime in via the comment section below — but some success expert pointed out that the moment you give yourself a plan B, you’re giving yourself an easy way out. The moment you give yourself a plan B, you’ve almost already given up on plan A. Maybe there’s some truth to that. But, there is also something to be said about risk management, even if you dare to dream.

Know When to Hold ’em

Most of us want to be optimistic. After all, why would we start something if we thought we were going to fail at it? No one starts a blog or a YouTube channel expecting to fall flat on their face. And, absolutely, there is a lot to be said about the power of perseverance and your willingness to stick with it through the hard times.

There is no such thing as an overnight success. And, you just might trudge through weeks, months or even years of creating content before you hit anything that resembles a “big break.” To that end, many people will tell you that just have to stick with it, and that fortune not only favors the bold, but also the persistent. There’s some truth to that. At the same time, you also have to recognize when it’s time to move on to something else if your original thing isn’t working out.

Do you remember the Pareto principle? While part of that philosophy says you should focus your efforts on what is delivering the greatest results, the flip side is that you need to abandon the aspects that aren’t pulling their weight.

On Eggs and Baskets

Speaking of the Pareto principle, it also ties into a “common” nugget of wisdom: don’t put all your eggs in one basket. As online entrepreneurs, we have this habit of dipping our toes into many waters, often at the same time. In addition to this blogging and freelance writing thing, I also dabble in photography and videography. I’ve published books and I have an active YouTube channel. Some people look into podcasting or online courses or selling merch or affiliate marketing or any number of other possibilities.

That’s a big part of the freedom that comes from leading such a professional life. At the same time, we also have to recognize that we can’t spread ourselves too thin. When you invest yourself in too many projects at the same time, none of them are really getting the care and attention that they need. It is far better for you to invest 80% of your time in one basket with the greatest chance of success than it is for you to invest 10% of your time in each of eight different projects.

In this way, a healthy dose of pessimism can actually serve you remarkably well. You only have so many eggs, so you have to choose how many baskets you want to balance. The pessimist in you will see that some projects have a high chance at failure, so they’ll need to be cast aside. You need to learn to let go, so that you can really dig deep into something that might work.

The Contingency Plan

Sure, some people will indeed assert that having a contingency plan is the first step toward inevitable failure. I disagree. Rather, it would be foolish to hurl yourself headlong into a grand scheme without a safety net. You can start blogging part-time while holding on to a day job, building up an emergency fund and growing that online business until you get to the point where you can reasonably and justifiably take that leap of faith.

And then, if everything happens to go sideways, you’ll sure be glad that you have a contingency plan in place. And you can thank that little bit of pessimism for keeping a roof over your head and food on the table.