Hard-Earned Advice I Don't Want To Forget

If you’re looking for fantastic life advice, a good friend just posted 35 lessons from 35 years of life (Sahil Bloom). You should read it. It’s fantastic.

I shared it and a few people asked “what would you add?” Being a bit older and more experienced than him (by 20 years!), there are a few additional lessons I’ve learned over the years.

Reading them one more time before I hit the publish button, I realized the additions are a good reminder for me as I head back into the Builder’s seat for the third act in my career.

1. Grit = Vision + Control

Most definitions of grit fall flat. Courage. Conscientiousness. Perseverance. Resilience. Passion. These words sound right but they don’t help you understand whether you actually have it.

My definition is cleaner: Grit is Vision plus Control. Vision is a future state you desperately want to become real. Control is an unwavering belief that your actions will affect whether it materializes.

World-class athletes have grit because they want to win championships and believe that practice, diet, and discipline will get them there. The vision is clear. The belief in their own agency is absolute. That’s grit. Everything else is just vocabulary.

2. Get Your Wiring Right

The most successful people I’ve met have their ears wired to their brains, not to their mouths.

Ear-to-mouth people struggle to learn and grow because their energy gets wasted hearing themselves talk instead of letting themselves think. They’re already formulating their response before the other person finishes a sentence. You’ve been in rooms with these people. You might be one of them. I’ve certainly been guilty of it (a lot).

Learning happens ear-to-brain. Then you prove you know something when it moves brain-to-writing or brain-to-conversation, but only after you’ve developed a sharp perspective. Not before.

3. You Have Hours, Not Days

When you piss someone off, you only have a few hours to make things right. Not days. Hours.

Co-workers can’t be expected to see eye-to-eye all the time. But there’s a moment when disagreements stop being about sharing opinions and start being about “I’m right and you’re wrong.” Aware people can tell when a conversation takes that turn and someone leaves a room upset.

You don’t have much time to address the situation before that person locks in a view that you’re a jerk. If you admit the conversation went sideways, apologize, and offer to reboot with an open mind, you can reverse what could become a poisonous relationship. Wait too long and it’s permanent.

I learned this one the hard way. Early in my career I had sharp elbows and it cost me. Now I appreciate how powerful this concept is and try to help others learn it earlier than I did. It might be one of the most important EQ skills you can build.

4. My Dad’s Voice in My Head

When I was growing up, my dad constantly told me: “You can’t complain about the results you didn’t get from the work you didn’t put in.”

I heard this so many times it’s burned into my brain. I hear it all the time. For 32 years nobody has been able to outwork me. I don’t complain. I do the work. At 55, heading into Act 3 of my career, I just have to remind myself that there’s still no substitute for putting in the hours.

5. Report to the Truth

In the immortal words of Jack Black: “This is not the greatest song in the world.”

Admitting that something isn’t working is one of the hardest skills to develop. We get attached to ideas. We confuse persistence with stubbornness. We hold onto things longer than we should because walking away feels like failure.

As I head back into building again, I need to surround myself with people who report to the truth, not to me. Every Founder should fear blind followers, especially Founders who people look to for guidance given their experience. I don’t want agreement. I want the truth. That’s the only way to know when something isn’t working fast enough to do something about it.

6. Help Others First

This is counterintuitive for alpha-type personalities, but I’ve learned that helping others succeed is the best way to get big things done. You only have one voice, and using it to convince others that your projects are at the top of the priority list will often backfire.

When you help others by prioritizing their needs over your own, you build an army of supporters. And an army is louder and has more power than any individual. Don’t worry. You’ll find ways to get your own work done even after putting others first.

7. The “Why Now?” Is Everything

If you’re trying to accomplish something big, make sure you have a phenomenal answer for the question: “Why now?” And to be clear, “me” isn’t a good answer.

No matter how good an idea is, poor timing has the gravitational pull of a black hole. It’s inescapable. I’ve seen brilliant Founders with novel ideas get crushed because the market wasn’t ready, the technology wasn’t there, or the regulatory environment was hostile. Timing isn’t an equal variable among many. It’s the main variable that dominates all others.

8. Actions Live Forever

Doing the right thing daily compounds over time.

For Founders, this compounding has a profound impact on your team, your customers, and your stakeholders. Culture isn’t what you say. It’s the accumulation of what you do.

For investors, today’s deals are won or lost based on the totality of how you’ve behaved in the past. Your reputation arrives before you do. I lived this for 18 years and know it to be true.

As I start Act 3 of my career, I’m hoping that 32 years of treating people well, acting with positive intent, and helping others selflessly in the startup ecosystem will somehow help when I need it most. I’m setting out to build something very difficult and very big. It’s something that could become my generational legacy. Since every action echoes forward, I’m hoping my past actions make the path forward a little easier.

Onwards and upwards,

Fintechjunkie