The biggest mistake I ever made

Updated to Business on December 18, 2022.

It’s hard to write an article about avoiding mistakes in business when you’ve made thousands of them. It’s like sitting down to write “Everything I know about love” when everyday you are painfully reminded you really don’t know much.

All my businesses have been pretty different. But, when I think back to scrounging up money to pay for another flight into the frozen barrens of Antarctica, suffering through an all-nighter dry walling someone’s basement (a short-lived renovation company I would rather forget about), or presenting to the three people that showed up for my first seminar, there was one reoccurring mistake.

I didn’t get enough advice.

Michael Gerber does a brilliant job describing the challenges of growing an entrepreneurial business in his best-seller The E-Myth Revisited.

And one universal challenge (Gerber doesn’t put it this way, but I know he would agree) is that entrepreneurs have a big ego.

Listen to interviews of successful entrepreneurs, or read their autobiographies, and one pattern emerges. They have a big ego. Of course, everyone has an ego – you can’t function without believing in yourself. But we entrepreneurs have it in spades.

And what goes along with ego is saying ‘no-go’ to advice. We don’t admit we need advice and, even if we did, we don’t seek it enough.


It could be a simple question, like: should I add a widget on the side of my web page. Or a higher stakes one, like: what should I charge? Or should I create an app for my business?

Why would we not ask for advice? After all, there is always someone who has done exactly what you want to do and has insights you can learn from. But something happens when you contemplate asking others. Maybe you wonder if you even know anyone that can help, or maybe you worry that if you do find someone, they might refuse your request.

Either way, advice is like gold. It might take some work to get it, but once you do, it’s invaluable.


If you follow the theory of six degrees of separation then you understand that the person you need to ask is within reach. This theory states that everyone you want to connect with is just six steps away, by introduction, from someone you already know. Here are two recent examples:

Last week I needed an employment contract for my employee, Sarah. Two emails later I had two versions to work from. In fact, I actually found Sarah by asking friends.

Guy KawasakiI wanted to interview Guy Kawasaki for my podcast. I asked Jaime Tardy how to reach him and two emails later he was booked (BTW you can enjoy that interview here).  


Of course, you will feel a little hesitation before you ask someone for help. That’s human. That is just your six-ounce buddy the Amygdala watching out for you. My advice is: listen, say “Thank You”, and do it anyways.

When I wanted to create a mastermind group I just bit the bullet, phoned three people and asked. Of course, I felt a little hesitation before each call (I’d be worried if I didn’t), but you learn a lot by pushing through and making the call.

When I wanted to launch my year-long coaching program I just picked up the phone and started dialing. I started with people I knew and asked three simple questions: what content would serve you the most? Who do you know that would benefit from this? And are you interested in joining? Within three weeks the program was full.

What about for you?

What are you working on right now that could do with a little outside perspective (or maybe even a little dose of “What the hell were you thinking!??”)


  • If you have a book draft, call six people (Yes call – don’t email) and ask if they will read and review it.
  • If you need help with marketing get on a forum, LinkedIn or Facebook group and start asking for advice.
  • If you have a list, you can send a simple survey (Survey Monkey lets you ask up to 10 questions of 100 people for free).
  • If you have people in your community you want advice from, call or email and ask if they would meet for 30 minutes to share their journey. The approach that usually works for me is a request something like:

Dear Hugh,

I was just talking with  ########### and they spoke highly of the work you are doing. I’m new to the business and have lots of ideas. And I know I could learn a lot from you and your successes.

Can I buy you coffee either this Tuesday at 1:30 or Wednesday at 10:30 (I promise to keep the meeting to 30 minutes)?

Thanks and please let me know if either of those times work for you.

You will be surprised by how many people are willing to help. All you have to do is ask.