Why Some Succeed Where Others Fail

Two tall cliffs

The Problem Is Not The Problem.

The Problem Is The Way You Think About The Problem. ~ Dan Sullivan

My “job” is solving business problems for my clients. I get the pleasure of thinking about other people’s problems.

This has carried over into Foolish Adventure where I teach people how to solve the problem of entrepreneurship — mainly from a lifestyle design perspective to give people the freedom of Time, Income & Mobility.

In a recent email, I talked about the “5/15/80 Rule.”

We’ve heard about the 80/20 Principle, but the 5/15/80 Rule is the break down of achievement — 5% are very successful, 15% are somewhat successful and 80% are not successful.

This achievement stratification occurs in every endeavor.

Business? Check. Weight loss? Check. Retirement? Check.

But why? Why don’t more people accomplish what they want in life?

Why doesn’t Tom quit his job to start the yoga studio he’s always dreamt of having?

Why doesn’t Katrina triple the revenue of her accounting practice?

She has a plan she thinks might work. She is the sole decision maker in her business — she doesn’t have to get approval from a boss.

Why do Steve and Ed pick an idea they don’t have any experience in and build a software company that reaches $2.5 million in revenue is less than 3 years?

Before I try to answer those questions let me admit that I’ve been in all three spots and I’m in the middle one now.

I wanted to start a magazine about comic books back in the early 1990s. I had an idea. I had friends that would and were helping me. I figured out how to get it printed and distributed.

What stopped me? It was going to cost $300,000 of which I had maybe $300 in my bank account. But that’s not what stopped me.

I quickly found a way to raise half of what I needed by preselling advertising. We thought we could even sell as much as $200,000 in ad space.

I just needed to find another $100,000 to make this plan a reality.

That’s when I panicked.

I didn’t have any experience in publishing. Hell, I did environmental work in the Air Force for a living. I was 22 years old. Who was I to think someone would give me $100,000 to create a magazine about comic books?

That question is why I failed.

The problem wasn’t that I needed to raise $100,000. The problem was how I thought about raising the money.

I even knew how lucky I had been the whole time. I had over 30 people who were excited enough about this magazine that they were donating their time and talent. I had veteran industry experts providing me with advice and assistance in selling the ads, setting up distribution. I had contacts in the industry that would help me sell the magazine throughout North America.

It was all happening quickly and, well, easily. So why couldn’t I believe enough in myself that I would find a way to raise the rest of the money?

What happened was as soon as the self-doubt crept in I couldn’t shake it. I was scared to admit my fears to the people who were helping me. What if they abandon me if I show them my weakness? If I ask too many questions of my mentors, will they think I’m an idiot and stop helping me?

I retreated into myself and I quit. I quit before the magazine ever had a chance to prove itself.

The market proved itself. Other magazines popped up. One did really well and sold for millions to a larger publishing company. That could have been my magazine.

But I’ve been in the 5% too.

I entered the swimming pool service industry with zero knowledge other than people swim in pools and it gets really hot in Phoenix, Arizona.

Within 2 years from my start, the company was generating $50,000 a month in revenue from a small team. In comparison, the average pool guy brings in revenue of about $50,000 a year.

In the vein of being authentic (see the most recent episode), I’m in the 20% right now.


Lack of focus. Enjoying my free time more than wanting to increase my income as I’m nearly at the marginal utility of money (a discussion for another time) in my personal life.

But these are just excuses. A rationalization of the self-doubt that I’ve struggled with all my life. Even though I don’t have any real reason to doubt myself after all the things I’ve achieved and I know I’m capable of achieving.

I let those fears manifest into taking on too many projects so I can’t do them to their fullest. A little here. A little there. And the result is being in the 20%.

I’ve known this for awhile and used my Foolish Motorcycle Adventure as a time to get clarity.

I’ve turned down 3 potential clients and referred one project to a friend this summer — a potential income of at least $75,000, so I could focus on just a couple of things.

1. Changing how I teach entrepreneurship by having just 2 programs of the same content — a live course (registration closes soon) and a self-paced course.

2. My mastermind groups. I run one mastermind group for experienced and growth-oriented founders. And I’m starting one inside Foolish Adventure for relatively new to intermediate entrepreneurs.

I used my journey as a way to illustrate that the problems we face are not the problem. How we think about those problems is the problem. The difference between being in the 80% who fail and the 15% and 5% who succeed is a matter of how you think.

Many times the problem isn’t as difficult as we make it out to be. What looks like a vast chasm to leap turns out to be just a hop away — after we leap.

Fear distorts the problem making it look insurmountable. Then our brain works overtime to give us reasons why the problem is in fact impossible to overcome.

We all have this reaction. Every human does. And when you are experiencing this reaction you need to open up. Don’t retreat back into yourself like I’m prone to do.

Surround yourself with people who will listen and encourage you. That will hold you accountable and kick you in the ass when you need it.

Find mentors who will help you overcome your self-doubts and give you a new way to think about a problem.

When you get to the edge of your problem’s cliff…

And your sweating, shaking and freaking out…


Your success will be found while in the air.

Enjoy your Foolish Adventure,


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This article was an email that I sent to FA email subscribers. It created a flood of email responses about how it was what they were going through.

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  1. You’re the man Tim… great post. I’ve been working on this very idea the last few days, that our role is to just organize the abundances around us, it’s not the world that’s lacking when things don’t get done (money, market, resources)… the world’s just fine… it’s always seems to be good ole us. ! 🙂

    1. Thanks, Dan.

      I talk about the inner game stuff everywhere except for here on FA. Not sure why I’ve held that back. But I’ve decided to start sharing some of mental aspects to succeeding at changing one’s environment.

      Let’s record an episode to talk about this stuff.

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