Life is Hard. It’s Harder When You’re Stupid

Avoiding simple mistakes in business

Aaron Webber
4 min readSep 9, 2019

My wife Karrie has a wonderful friend in a neighborhood who we will call Heather. Heather has a favorite saying when she’s chatting with the ladies, “Yes, life is hard, but it’s much harder when you’re stupid.”

That’s a bit blunt, but sometimes bluntness arrests our attention such that it gets our focus more than a politically correct or nicely-worded, friendly, soft statement.

I’m going to be similarly blunt. In business and in life, just don’t be stupid. Don’t do stupid stuff. You could express that algebraically as: id2s2. In fact, I have an icon on my phone that has that equation on it as a piece of artwork to remind me that ‘I don’t do stupid stuff.”

It’s a great reminder when you’re in the heat of the moment, and you want to rush forward without thinking. It forces you to say, hang on a minute, is this something stupid, something I will regret? Something that I’ll maybe need to spend a lot of time and effort to undo?

To put some flavor around what stupid stuff I mean, let me share with you some things that are either stupid stuff, or the solution for some stupid stuff.

If you’re in management, or leadership, if you’re a founder or CEO, or someone that leads a team, are you actually using the team properly, or are you misusing, underusing, or even abusing your team? That would be stupid.

You’re hiring people for their attitudes and their skill sets and their abilities in the hopes that they will grow into being more skilled and more able. It’s all sorts of stupid if you don’t allow them to grow, don’t allow them to do what you’ve hired them to do, and don’t allow them to deliver results beyond filling a seat, or acting like your personal therapist when things go wrong or you’re having a bad day. Let your people do what you’ve hired them to do. You are paying them to do their work, your job should be to clear the decks to allow them to do that work.

Your leadership function should be to grow them beyond that which they thought they were capable of by themselves.

Next, don’t make the same mistakes that others have made. That’s stupid.

Be well-read. Look around you, learn from the success stories (and the principles that underlie those success stories), but more importantly, learn from the failures of others. What did they do wrong? What did they learn? What are they prepared to confess that they did wrong? What can you infer they did wrong? Learn from the tuition payments that others have made.

There is no monopoly on brains, as one of my old my old bosses would say, so look around you. Learn from your own experience and the experience of others. Watch what they’ve done well and what they’ve done poorly.

Three is find a mentor. It’s stupid to not.

I don’t care what role you have, find someone that can help you be better. Find someone for whom you want to be better. Find someone that can, in a kind way, speak firmly to you when you’re off track. In other words, having a person to productively check your progress, is not stupid. That is time well spent. Thinking you can do it on your own or that you know it all, is stupid.

Finally, (this happens all too often, and if you catch yourself going down this slope, stop immediately) don’t believe your own press releases. It would be stupid to do so.

No one else believes your press releases. So, why should you? We all know the function they serve, we all know that they tend to gild the lily just a little bit. Don’t start believing your own press releases. Don’t think you’re “all that.” Don’t think that you can walk on water. You can’t.

Yes, you’re good, you’re skilled, you’re hard-working, but you’re not quite as good as the press releases make you think you are. Keep yourself grounded, keep yourself focused.

Now I can go on and on and depress you with a whole list of other stupid things that you shouldn’t do. But suffice it to say taking the moment to decide whether that thing that you’re about to do falls into the stupid/less-than-stupid/non-stupid categories is a fruitful endeavor.

As Heather says, life is hard. Business is hard. Growing one and being successful in it is extremely difficult. It is significantly more difficult when you’re stupid.

So easy solution… don’t be stupid.

Aaron Webber is a serial entrepreneur and CEO of Webber Investments LLC, as well as a Managing Partner at Madison Wall Agencies.

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Aaron Webber

Chairman and CEO, Webber Investments. Partner at Idea Booth/BGO.