Try failing more

I remember back when I started my business, I had a lot of wacky ideas.

I printed flyers and slipped them under the door of the downtown businesses. I set up a system to help non-profits collect donations specifically earmarked to fund a website. I posted my services for sale on Facebook Marketplace.

All of those (and plenty more) failed to deliver any kind of result.

But a few ended up being a home run; offering a retainer for web work (before I knew what a care plan was), volunteering at a non-profit (where I made relationships with the board members who were the “connectors” that happily opened doors for me), and offering low-cost printing services (that got my foot in the door at a ton of local businesses).

I had no idea what I what was going to work — but I was out there doing it anyway.

Eventually the business stabilized, I built up a steady (enough) pipeline, and I stopped trying new things.

Of course, there’s value in focusing on “what already works”. It’s steady, predictable, and responsible. But it can also be a trap.

The world around us never stops changing. It’s always experimenting with new ideas. In the last 18-24 months, our world is changing faster than we’ve ever experienced.

Those things that “already work” — our status quo we’ve become so comfortable with — won’t work forever. Nothing does. Which means the only way to keep up is to keep running experiments, knowing full well most of them won’t pan out.

Failing sucks. And the more successful you become, the more uncomfortable it feels. Now that we’ve got something to protect, it’s natural that we try and avoid it.

But I didn’t figure out retainers, find connectors, or come up with a good foot-in-the-door offer because I was smart enough to predict what would work. I found them because I ran all the experiments — including the losers. Every flop taught me something I needed to learn in the way that only experience can deliver.

Standing still is way more dangerous than trying and failing… At least when you fail there’s something to learn. Standing still won’t teach you anything.

I’m not suggesting you go out there and do dumb stuff just to fall on your ass. But failures are the only honest evidence you have that you’re still moving forward and you haven’t slipped into maintenance mode while the world around you whizzes by.

When was the last time you ignored that little voice in the back of your head saying “but what if it doesn’t work”? When was the last time you went for it and ended up with a few bumps and bruises?

If it’s been a while, that may be a sign you’re living a little too comfortably.

So pick the thing you’ve been putting off… One offer, one email, or one service pitch. A small enough test that being wrong costs you nothing more than an afternoon.

Do it not with the intention to fail, but with the confidence that either way, you’ll come out the other side knowing something you don’t know right now.