Find Someone Who Knows Their Sh*t, Then Shut Up and Listen


It’s odd when you think about it: We were smart enough to know we needed someone with more experience in this area than we had, but at the same time we were dumb enough to throw almost all of his advice out the window.


Quick Note: Things are going well on this New York business trips in terms of me keeping up with the posts. The bad news is that I don’t have my art software and/or tools with me, so you get no fancy images at the top of the post today. I’ll add them retroactively when I get home this weekend.


We are very fortunate in that my wife and I have an Uncle who has been a Financial Advisor for the better part of 50 years. About two years before we hit our financial crisis, we reached out to him and asked for help in getting things in order. I think we had realized that we had kept the debt monster in the closet for far too long, and it was about to kick down the door and eat us in our sleep.

Our Uncle is a fantastic human, and so not only did he agree to sit down with us, but he agreed to provide long-term guidance free of charge.

Think about that for a moment: A person who is financially sound –wealthy in fact– with a healthy list of very successful clients, was 100% willing to provide guidance to us at absolutely no charge, and do so with no set end date. We could use him until we felt secure.

Pretty baller.

So we met with him and he started to advise us on a financial strategy. Up until that point, our investing knowledge consisted solely of blindly throwing money into a 401k each month and not much else. He started teaching us about diversification, opening up a Roth IRA, building a stock portfolio, and more. He also told us that we were making some silly mistakes with our money, such as throwing all of our cash into a vacation, versus saving part of it, even if it meant putting the vacation off a few months longer.

This man told us how to kill the monster in the closet.

We then promptly went out, ignored all of his advice, smothered ourselves in BBQ sauce, and laid down in front of the closet door and patiently waited.
Looking back on it now, we were oddly arrogant about our approach to his advice. We didn’t mean to be, but in a subconscious cocky manner we squished his advice with our own dumb thoughts:

“Oh I’m sure we don’t need to be that concerned about our lack of savings. We’re still young!”

“What does he mean our cash flow is low? We are paying our bills.”

“Why diversify when the 401k is making us money?”

“Hey look! The monster ate my arm!”

For nearly 18 months, we did nothing that he told us to. We didn’t do it 100% on purpose, but we kind of tossed out every item of advice he had given us.

Can you guess what happened? I bet you can!

We bought a new house with a new mortgage payment, we bought a gigantic new truck for my wife with a gigantic new payment, we went to Disneyland, we had a GREAT time!

We also totally stopped meeting with our Uncle, the Financial Advisor. Now we were covered in BBQ sauce at the closet door, actively yelling “HEY STUPID MONSTER. WHY DON’T YOU QUIT BEING SO STUPID AND COME OUT HERE AND EAT US!”

I’ll stop with the Monster analogy now. You get it.

And then just like that, before I even had all of the Disneyland churros knocked out of my beard, we were talking about contingency plans to keep from losing our home.

If we had just listened to that awesome Uncle with the free advice, things would have been totally different. We wouldn’t have that new truck, and we probably wouldn’t have that new house, but we also wouldn’t have the horrific situation we got ourselves into.

It’s odd when you think about it: We were smart enough to know we needed someone with more experience in this area than we had, but at the same time we were dumb enough to throw almost all of his advice out the window.

We let our ego get in the way.

We decided that ultimately we still knew better. We were adults who had gotten ourselves this far in life, and damnit, we could figure this out on our own! So we went on not just making the same mistakes, but even upping our game to even bigger and dumber mistakes than we ever had before.

So my advice is this:

  1. Whether in business, in athletics, in finances, or just in life in general, go out and find yourself a Mentor. Find an area of your life that you really want to improve in, such as understanding financial planning.
  2. Once you’ve identified your “area,” it’s time to find your mentor. Take your time, talk to lots of people if you don’t have a good top-of-mind option, and pick someone who you truly trust and admire.
  3. From there comes the convincing part of getting them to agree to help you, but I’ll leave that up to you and your charming personality to pull off.
  4. And then comes the most important step of all: Once you have identified the area, researched your Mentor, and convinced that person to partake, ABOVE ALL ELSE listen to the advice of that person.

The real kicker of all of this? I can almost guarantee that the mentor you select has (or had) a mentor of their own. They didn’t know everything about everything from day one, they fully understood that fact, and they found guidance in others who they believed in.

Check your ego, and take the advice you are given. If we could just rewind those 2 years, we absolutely would, and we would have listened to and applied all of the advice we were handed for free.

I’ve learned from my mistakes. I meet with that Uncle on a regular basis, and have at least one recurring call with him every single month to make sure I am making the right choices and putting my finances back together properly.

I guess now I just need to find a Mentor with experience in building time machines.


2 thoughts on “Find Someone Who Knows Their Sh*t, Then Shut Up and Listen

  1. Think about the cumulative knowledge in a Mentor’s portfolio: he learned from his, who in turn learned from his, etc. Obviously, not everything is absorbed from Senpai to Kohai, but there’s way more than one person’s experiences there to learn from.

    Liked by 1 person

  2. Wow, I am really moved by this article. A lot of people do not realize that free advise is actually valuable. You could have not have said it any better. Will definitely share the insight I have learnt from here with my friends. Do give us a progress update for motivation.


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