Why Seeking Success Might Be the Worst Mistake of All – Midsummer Special (FSFS222)

A long time ago, I thought of trying my hand at running a marathon. I’ve never run a marathon before, and heck, I was never even a runner. But I thought it was something challenging I could do, so I gave myself nine months to train for it. 

I don’t know a lot about running marathons—I didn’t even do my research. I jumped in. And looking back it now, that probably wasn’t the best approach to go about it.

I think a lot of people going into business do the same thing. Fueled by passion and excitement, you go for the jump. And suddenly, you find yourself doing it and thinking you’re not practicing smart, and you’re not doing all the things you should have been doing.

Nonetheless, I started running. When you train for a marathon, you run. So, I ran. A lot.

I got into the grind, and I realized that taking on a marathon is like taking on a second, part-time job. It’s not like training for a hundred-meter sprint, you’re covering a lot of ground. Not everyone is Eliud Kipchoge, so training takes a long time. Running 20 miles an hour and doing 5-minute miles take up time.

Where do you fit that into your life? It’s not something you stumble into—you have to be strategic and plan that into your life.

You might not have run a marathon in your life, but I can guarantee you’re running in one marathon right now. The marathon of life.

One story that has always resonated with me is approaching life as a race like a marathon. Sometimes we’re just running without knowing where we’re headed, or why we even started running until one day, we stop and look around us, we think, “how did I get here?”

That’s how life is for a lot of people. We start something and put ourselves into it, but one day, something snaps, and we think, “what am I doing? Is this even what I wanted to do?”

Where are you in the marathon of life? Where are you going? Why did you start running?


Success? Fulfillment? 

Today is another show about context—one thing I think is so missing in the business world.

Why do you do what you do? There are all these things that should shape your decision-making process.

Sometimes the cruel irony of entrepreneurship is we fall back into the cycle we had when we had that corporate job: we go to work everyday just to get the work done and we do it again the next day. We just go through the motions.

As business owners, how often do we just go through the motions? I know I do it a lot. But then what happens is that the freedom we sought with entrepreneurship disappears and we start living the same life we did as employees, except we’re our own bosses holding ourselves to the same standards as our old bosses held us before.

I think a lot of Western culture pushes people toward success. On the surface, it sounds great. The goal of success is getting from A to Z. For a lot of people in the West, it starts at a young age. From grade school until you graduate college, it’s go to school, get good grades. After that, you get a job, work your way to the top, retire, and that’s it. You succeeded.

But what about that time in between?

I’m going to argue in this episode that success isn’t really what we’re after. It’s fulfillment that we should be after. If success is getting from A to Z, fulfillment is what happens on the way to Z and beyond. It’s running your race with your head up, looking at everything around you, and talking to the people next to you instead of keeping your head down and running as fast as you can because someone said you have to get to the finish line before someone else.

Be conscious that the sands of time are flowing through your fingers faster than you could ever imagine. Don’t waste your time looking down and look up at the fulfillment you should be taking in every day before it all ends.

We can go at any time, the people in our life can go any time. Don’t get so fixated on success that you miss time with the people you love and care about. Think about the fulfillment of the journey.

We think about success in a traditional business context—increasing shareholder value, growth ever quarter, promotions, pay raises, awards, prestige. Say your business is financially viable, sustainable, and you’ve saved enough for a rainy day and even a bit more to pass on to your kids. After that, where do you want to go?

Do you want to make your business bigger and better because that’s what someone else is doing? For bragging rights? Instagram success?


“What do you want?”


When you’re running a lifestyle business and you’re seeking fulfillment over success, work stops becoming work.

Instead of formal business success where you seek retirement, I think of my business as a living retirement. I used to work in a stock brokerage where success was measured by how well portfolios were doing, how well the market was doing, what the bonuses looked like. And it all felt shallow. It felt hollow and sad. It’s a narrow vision of life and success.

What initially looks like a success escalator is actually a success treadmill because you’re just running on it, doing the same thing. Take beating your best sales week for example. After you beat it, you have to beat it again. And do it again. And again. And again. It’s to infinity and beyond. Where does it end?

So, we can be content being further down the ladder. Or realize that while we’re trying to go up the ladder, we realize that that’s not what life is all about. We’re going to enjoy the view along the way.

When we think about success, it’s a point out there that many people aim to be in, and that’s great. But we should remember to enjoy the journey along the way.

I agree with Alan Watts when he said that success is not a point in front of you, it’s everything all around you. It’s something you’ve always had inside you but sometimes fail to realize that this is what success is.

If you’re doing something you love in a place you love, that is success. You can smile about it and be thankful that you’re in this place.

If we shift ourselves from achieving perceived success, life now becomes about family, friends, personal achievement, and living who you are.

Wake up and don’t let life pass you by because it can all end in the blink of an eye. 



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