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Making Mistakes vs. Repeating Them

David Sherry
5 min read

I’ve failed more than I’ve succeeded.

I’ve hit more dead ends than open doors.

In high school, I was a leader on many sports teams. I also missed shots when it was critical in the game to make them.

In college, I tried to start a Startup Magazine and… quit because it wasn’t going anywhere.

I tried to start a bike lock company, and quit because it wasn’t going anywhere.

I pitched a campus-related startup idea to investors and got totally rejected.

I pitched brands to be their photographer and was rejected.

I got involved with a Skin Care company and quit because I wasn’t sure what my role was.

I’ve had all types of plans that didn’t work.

I just tested out a membership site and then stopped it because it wasn’t right, and needed to improve. I actually got some of the most generous feedback in my life from a member who cared, who said: “I honestly don’t know where this is going.” Ouch, but thank you so much, truly.

Each test exposes weak points. Each failure surfaces new understanding.

I don’t think you can get away with not failing much of what you try. But I also don’t know if I really consider it a failure. Failure is sort of a harsh word to use. They’re more like roadblocks or mistakes that lead to learning. These mistakes are critical aspects of what happens moving forward, so… it’s all a forward progress and an upward trajectory.

On the path to mastery and learning a skill, there is practically an unfathomable amount of depth to understand. Think of learning like a blue hole. Before you start, you only see the surface. You think – “oh, that’s the area that I need to cover? That’s not so bad, I can at least see how I could swim to all of the edges. ”

But then you realize the water is 1,000 feet deep. You need a flashlight to see and can only learn a few feet at a time. It takes a long time to explore that, and even after you keep diving and diving you’re still discovering new areas.

The really tough times are the times that you feel like you are repeating the same mistake twice.

This happens because you’re not understanding something, and thus the problem surfaces again. You’re stuck repeating the same patterns, and the same line of thinking when the truth is you’re living in a distorted reality. It could be childhood or adult related trauma that’s making you overly cautious, muddying your thinking. Or maybe the reverse is true – you’re not thinking ahead and throwing caution to the wind.

Regardless, there’s no point in being too hard on yourself. Life is complex. I don’t think we can truly comprehend the number of events that have to coincide simultaneously for something to work out. Your internal world, the external world, the actions you take, the culture, the packaging, momentum… it all needs to be this huge synchronicity.

But the good news is there is a way to position yourself for these synchronicities…

It’s simply to keep pushing forward, to keep taking action, and to keep taking your best shot at creating them. Skills help you pattern match. Mental toughness and resilience from previous mistakes give you the guts to keep going. Small moments from conversations or something you did offhand bubble up as important pieces of the puzzle, Slumdog Millionaire style.

I’ll add a caveat here, though. If you keep pushing forward without taking a pause to look at the patterns that are causing recurring mistakes, recurring fights, recurring pain, we’re missing the fastest way to grow.

We need to hit pause and understand. While the majority of our efforts should be spent with grit – doubling down to force something that isn’t working is a clear sign that you are missing some understanding that would help you move forward.

Everyone has areas of their life that seem to be stuck in a holding pattern. Some are killing it with their career but can’t figure out their relationships, others are in great relationships but have a hard time with their career. Or maybe working out and eating healthy is a daily struggle, while you don’t even think about nailing the presentation in front of a crowd.

When you hit pause, you give yourself the ability to isolate this area and understand what you’re missing. You get to be humbled. If you don't’ pause, you don’t get to admit, out loud, that you're stuck or that what you've been doing in the past simply isn’t working.

We fear admitting this to ourselves… why? I’m not sure – our egos want to cover up the pain by racing forward or numbing with alcohol or cheap entertainment. Which is funny, because doing that simply kicks the can of pain down the road. You will meet it again.

But stopping, seeing clearly for the first time and saying out loud “hey, maybe I’m struggling in this area and rather than continuing to struggle, wouldn’t it be easier to admit it to myself and actually discover a way to drop this pattern?”

That’s the way to turn over some stones in your life, and upon seeing what’s underneath them, you can let them go or at least toss them aside to rarely pick them up again.

Which is amazing – can you imagine how much time and energy you’d have back if you weren’t bumping into this rough area on repeat every so often? Can you imagine letting that go… just dropping it because you understand now?

There’s another bit of relief that comes with this, which is psychologically dropping the nagging questions in the back of your mind, which continually pose a threat to how you feel as a person.

That voice is so tiring, and so tireless because it hasn’t been addressed.

If you feel you have something like that you’d like to address – I’m hosting a series of 1-1 discussions, a 12 Week Program of reading, exercises and actions that help you raise the bar and deepen your understanding in a non-judgemental way. The purpose is to help you show up as fully as possible.

I’ve worked with business owners and creators from all over. I find that people with a lot of drive tend to feel this most often. It’s not uncommon that those who are the most successful struggle most here. Because the shinier the success in one area, the easier to cover up the block they have in another. It’s also not uncommon for people to reach out and say that they’d been waiting to have this conversation, they just didn’t know it existed or that there was a place to have it. So if that sounds like you hit reply and we’ll book a call to discuss what this looks like. I believe I have a keen eye for clarity, support, and reflection that leads people to find a lot of growth.

If it’s just a mistake or a roadblock on your path – you can keep moving forward, no matter how big or small, understanding that it’s simply further understanding and depth that you’re arriving at and will be useful later when things do work.

And if you’re running into the same snag, the same areas – instead of racing forward again and powering through, what if you did the opposite? What if you hit pause?

As always, let me know if I can help,

xx David