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Why The Most Expensive Mistakes Don’t Feel Like Mistakes

“It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”

Mark Twain (attributed)

Years ago, a friend of mine opened a flower shop. Early in the retail space selection process, she learned that the landlord of a suitable space was a heavy marijuana user. He also lived above the shop and was going to handle any necessary remodeling.

Both her business-savvy boyfriend and I immediately flagged this as an obvious problem, but she shut us down. The landlord’s pot use simply was not going to affect her business goal.

She was wrong.

During the remodel, which needed to meet a strict timeline, the landlord routinely missed deadlines and failed to follow through on crucial construction commitments. This made her miss an existential opening date and she ended up closing the shop within a few weeks of opening.

I felt very disappointed for my friend, but I also remember thinking:  Is this what happens when you’re usually the smartest person in the room?

My friend is very smart, but, like all of us, she also has blind spots. One of them, quite common among entrepreneurs, is optimism’s charming but reckless younger sister: overconfidence. In a one-two punch, it makes people overestimate their own competence and underestimate everyone else’s.

a pile of garbage sitting on top of a table

So why should you bother listening dissenters when you’ve found the perfect retail space?

Unlike mistakes which most of us can recognize, blind spots make us totally unaware of certain aspects of ourselves and by extension others. In that sense they can be lethal in depth and impact on our lives.

For example, I have wasted money in various ways related to my ignorance about business, learned from them and moved on to make completely different mistakes. So far so good. But about ten years ago I repeatedly made the exact same investing mistake and lost a ton of money.

After the shock and sting wore off, I went on a mission to figure out what drove me to do what I did. It was grueling and took a minute (ok 2 years) but I finally figured out that I had a major blind spot related to some childish need for an oracle in my life. In other words, a need for magic when it came to money.

I’m still embarrassed just thinking about it, but I also have created several fail-safes around my blind spot because I just know that I cannot trust myself around this kind of thing.

The point being that we make mistakes because we don’t have all the information about the situation yet, but blind spots are all about the missing information about ourselves. And, we all fool ourselves into believing that we see ourselves fully and clearly, but we don’t.

On the surface, one could argue that the lesson for my friend was to keep away from drug users in relation to business and that’s probably not wrong.

But the bigger lesson was that she cannot always trust her instincts and that because of that she should listen to friends who disagree, or at the very least, hear them out.

I witnessed this blind spot play itself out in my friend’s professional life repeatedly. And every time, no opinion but her own mattered when she was about to dive into the next venture that inevitably failed. The dots never connected.

So don’t worry about making mistakes because you will make them and that’s okay, but do worry about your blind spots when it comes to your business and even your life.

Because when it comes to everything involved in starting and then scaling a business, self awareness is an asset and a strategy.

Which is why I have created an exercise that you can do in a few minutes here and there over the course of your week and you can repeat time and time again.

  1. For a few minutes, casually ponder your weaknesses. Maybe it’s something your first girlfriend complained about or your mom has been bugging you about since you were five. Or something you just see in yourself.
  2. Reflect on how these have played out in your life, professionally or personally.
  3. Ponder how they might have affected the people in your life.
  4. Then ask a loved one, someone who you trust wants nothing but the best for you, if they think you have blind spots and what they are. Promise them that you won’t talk back. How have they affected the relationship?
  5. Listen. Compare it to your own list.

I wonder how often we miss an opportunity to learn something about ourselves because we don’t ask the people around us what they really think. We don’t give them permission or we get defensive when they try.

Change that, today. Try it, then write to tell me what you learned.

And if you’re wondering what happened to my friend, we lost touch ages ago, but the last thing I heard is that she is now a motivational speaker.

About the Author

Nadja Geipert, MA, LMFT

As a therapist, coach, and angel investor based in Roseville, California, Nadja works with ambitious people who are quietly struggling. Her clients include entrepreneurs, founders, creatives, and high-achievers who carry a lot but often feel isolated, burned out, or stuck. Her approach is honest, intuitive, and deeply grounded in connection.

Nadja holds a Master’s in Psychology from the California Graduate Institute and is a licensed Marriage and Family Therapist with advanced training in addiction, relationships, and trauma recovery.

With a background as a medical and science writer and an angel investor in over 20 startups, she understands the high-pressure worlds her clients live in from the inside out.

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About Nadja Geipert

As a therapist, coach, and angel investor based in Roseville, CA, Nadja specializes in helping high-achievers, founders, and creatives navigate burnout, perfectionism, and self-doubt. Drawing from both clinical training and real-world experience, she helps clients create meaningful change through insight, honesty, and deep connection.

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