I am an idiot #4 🙆‍♂️

Last year I met a really interesting guy. He was late 50’s, retired, uber successful in real estate investing, had travelled the world, and now spends his time volunteering. Super smart, super nice, it was like meeting a human superhero.

We spoke for about 45 minutes and I loved every second.

Just as I was leaving, he handed me his email address. He said if I wanted to get together again for coffee or something, I should shoot him an email.

This guy had a boatload of wisdom to share with me. He even offered to introduce me to some of his real estate contacts for mentorship and possible partnerships! I was so lucky!

I promised myself that as soon as I got home I would email him and set another time to meet.


When I got home, some doubt crept in… What if he just gave me his email to be nice? What if he really doesn’t want to meet with me?

A few days went by, I didn’t reach out.

What if his real estate friends are too big for me? What if I end up wasting his time?

A few weeks went by, I didn’t reach out.

What if he doesn’t remember me? What if he’s angry that I didn’t email right away?

It’s been over a year, I never emailed him. And now I’m too embarrassed.


The reason I share these “I am an idiot” stories is to a) make you feel less dumb if you do something similar and b) share lessons I learn to help make us not repeat the same mistakes.

If an impressive stranger offers to give you free advice, or goes out of their way to offer help… TAKE IT. Don’t be an idiot like I was.

Happy Thursday friends! Make it a great day,
– Joel


**Update…  I posted this at 5.45am and by 7am my inbox was full of encouraging responses and urges to email this guy – even though it’s been over a year. So I just sent him an email, and it literally took less than a few minutes. Thank you all. Here are some notes I received from you guys:

  • It’s never too late to try and correct mistakes
  • I’m only a real idiot if I let this sit longer
  • Don’t let “I am an idiot #5” be that you still haven’t sent the email
  • There is no downside to putting yourself out there
  • Never let embarrassment hold you back
  • “wer nicht wagt, der nicht gewinnt”, which roughly translates to “he who doesn’t take the risk will not win”. Take the risk!
  • What have you got to lose? What’s the worse that could happen?
  • Send him this post! He’ll appreciate the honesty and demonstrate your self education
  • You’ll always regret *not* emailing him. So do it.

Thanks for all the encouragement guys. Love you all.

– Joel

4 thoughts on “I am an idiot #4 🙆‍♂️

  • I wouldn’t be too hard on yourself. We’ve all done this. I took a quick look at my LinkedIn account and I have hundreds of connections there. If I just scroll down through them I see many where I have no recollection of how we met or why we’re connected.

    In the situation you describe above, one technique I’ve used is to simply write a quick thank you note via email. That way you keep the communication alive without asking for anything and without commiting anything. But keeps the door open for future discussions. Also, you can find that email later in your sent mail and reach back out to the person. Then, even if they don’t remember you, they can see the email history and know that they had a previous connection to you, despite not remembering it.

    • Thanks JR. I should know better. I was in sales for over a decade and following up is usually a habit for me. That’s why I remember this missed opportunity so clearly and feel so bad about it. I have the same LinkedIn problem as you – hundreds of names and connections with zero interaction.

  • Well, I appreciate your lesson!

    I have been trying to lean into my failures too. I notice that I have a bad habit of ruminating on failures so now I take the time to admit that they happen everyday and to specify the failure. For example yesterday I failed at practicing French and the piano but I remind myself that yes, I failed at that today but I am still happy and healthy.

    This allows me to not fixate on the failure but move forward in a positive way. Well, that is what I hope I am doing! 😅

    • Great mindset. Fixating on the failure is what lead to my embarrassment. Instead, I should have thought of the failure as a 1 time thing. Then, figure out a way to course correct. Good stuff! Thanks for reading and keep specifying the failures!

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