What Conventional Wisdom says: talk about your strengths, not your weaknesses.
But… what the path towards being a high-powered freelancer says: talk about your weaknesses (in addition to your strengths).
Let me explain.
Everyone has Achilles’ Heels, including you. I’m still assuming you, dear reader, are not AI. Maybe one day. Naturally, as you work closely with someone, your Achilles’ Heels will come out. It’s inevitable. Your Achilles’ Heels are, by definition, the source of your downfall. Although antiquity also argues that your Hubris will be your downfall—but that’s the subject for another chapter.
Bad news, you are exempt from this only if you are superhuman. And you’re not. This may not happen immediately, and it may not happen with client number 1 or number 2, but it will happen someday. Achilles’ Heels creep up on you when you least expect it.
Since your Achilles’ Heels will come out, and since it will be your downfall, a great strategy is to preempt them and deal with them immediately. One way to do so, for example, is to make a list of your weaknesses, including thinking deeply through them and then discuss this with any new client.
It sounds counter-intuitive; wouldn’t that scare a client or potential client off?
I suspect, and in my experience, it has the opposite effect. It’s not only endearing, but it’s substantially and significantly confidence-building. How so? A few reasons:
- It shows you understand yourself well.
- It shows your ability to wrestle with problems and work towards solving them.
- It shows you won’t avoid the hard or emotional issues, but you’ll confront them head-on.
Aren’t those characteristics of someone whom you’d like to hire? Yes, yes, and yes, no matter what the job is.
But on top of all those, it also shows how deeply you have your client’s best interest in mind, because when a problem does happen, he will be prepared, and any problem you are prepared for is 100x less bad than the same problem coming out of the blue. Had Hiroshima known of the impending nuclear devastation, they could have evacuated the city.
Imagine you hire someone. And on his first day, he tells you:
Listen, as we get started working together, I have to tell you about a crazy idiosyncrasy I have: I can get emotional too quickly if I feel connected to something. That’s good because it gives me the excitement and energy to work over the top. But it’s bad because sometimes I’ll get angry too easily and quickly. When that happens, my apologies in advance. I’m working on growing, I know I’m not perfect. Please bear with me when that happens.
What will you think? You’ll think this person is incredibly mature and you’ll be happy to be working with him or her! And even better, when the moment happens and he or she does get emotional you’ll be psychologically prepared, and being psychologically prepared, the negative effect will be a lot weaker.
Another way to frame this—perhaps this should be a different chapter, but these points are deeply interconnected—is that you should be the sort of person you want to hire. Look at the qualities of the employees you’ve hired or want to hire and ask yourself which qualities make you want to hire him or her again, or not. Emulate the best of what you see, improve on them. This is a classic, tried and true, but often discarded theory of self-improvement worth remembering: just relentlessly imitate and copy the best of what you see around you. And improve upon it as you do. It’s the copy-paste shortcut to actual growth. Of course, growing yourself is deeper and more important, but imitating the best around you is often an easy way to get started doing so.
And the hardest part of this, of course, is admitting to yourself what our Achilles’ Heels even are. Knowing yourself (gnothi seauton, the observation that was arguably the starting point of ancient Greek philosophical thought) is the start of wisdom, and shockingly hard.
