Why Running a Business Is So Hard (and Why It's Not Just You)

October 23, 2026•7 min read

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You look at other businesses online and around town, and they seem to have it all figured out. They have packed events, glowing posts, and growing teams. Then you go back to your own business, where payroll is tight, a key employee just quit, and you're up at 3 a.m. wondering what you're doing wrong.

Here's the truth: you're probably not doing anything wrong. Running a business is hard, even for the founders we admire most. In this post, I'll share the hard stories behind some of the world's best-known businesses and show how Focus, Flow, and Flourish help you stay in the game long enough to build a business that lasts.

In this episode

  • Why comparing your business to others' highlight reels makes you think you're doing it wrong

  • How a clear focus kept James Dyson and Cathy Hughes going through years of failure and rejection

  • Why grit alone isn't enough, and the systems that keep you moving when willpower runs out

  • The cash flow stress that nearly broke well-known founders, and how to avoid it

  • How to design a business that serves your life instead of costing you the games and birthdays

Resources mentioned

  • How I Built This with Guy Raz, 10-year anniversary episode (co-hosted with Ring founder Jamie Siminoff)

  • Grit by Angela Duckworth

  • Profit First by Mike Michalowicz

  • The free Two-Week Vacation Test: masteringbusinessflow.com/assessment

The Instagram Effect

We all know the Instagram effect. We see everyone's best moments, but not the scars and mess behind them.

We do the same thing with our businesses. We live with the day-to-day struggle of our own, then compare it to other businesses that look like they're flourishing. So we decide we must be doing something wrong.

Running a Business Is Hard for Everyone

On How I Built This's 10-year anniversary episode, host Guy Raz and Ring founder Jamie Siminoff looked back on interviews with more than 600 founders. One theme stood out to me: it was hard for all of them. There's no such thing as an overnight success.

  • Ring: Jamie Siminoff once built a trade show booth out of cardboard and tape in his basement. Friends who stopped by thought he was doing great. Inside, he felt like a total loser, and he said he wished someone had told him it was going to be okay.

  • Airbnb: The founders called 2008 the worst year of their lives. They had 20 introductions to investors and got zero investments.

  • Banana Republic: After working around the clock for three days on an early catalog, the founders woke to a honking horn and found they were driving the wrong way on the Golden Gate Bridge.

So here's the reframe. You're not different, and you're not doing it wrong. You're just not successful yet. The real question is what it will take to get there.

Focus: A Clear Direction Keeps You Going

Focus is a clear direction about what you want. It's one of the main things that keeps people in the game, because it gives you motivation when things get tough.

James Dyson didn't start Dyson until his 40s. He then spent five years building thousands of prototypes in his backyard shed. He could have quit at any point, but he believed in the bagless vacuum he wanted to build. No single failed prototype meant his brand had failed.

Cathy Hughes needed a million dollars to buy a radio station, and she had no collateral. She went to 32 banks, and every one said no. She went to one more, and that bank said yes. She didn't know it would, but she didn't let all those no's knock her off course. Today her company is Urban One.

Both of them knew what they wanted, and that gave them the determination to keep going.

Flow: Why Grit Alone Isn't Enough

Here's a word of warning: focus alone isn't always enough.

Angela Duckworth wrote the book Grit, which presents grit as a key ingredient to success. In the years since, she's found that grit alone isn't enough. You also need a system or environment that helps you stick with your goals, because it will get hard.

A simple example: if you don't want to eat sweets, don't keep them in the house. That's a system doing the work your willpower would otherwise have to do.

That's the Flow part of my framework, and each letter stands for a type of system.

F is for Filter

A filter helps you get clear on what you should and shouldn't be doing. The founder of Kinko's saw a copy shop with a long line out the door. That line was proof of demand, and it was a great filter.

If things aren't working in your business, you may not have used the right filter. You may have started doing things just because they sounded like a good idea. Before you invest, ask: is there a market for this? Will people really pay for it?

L is for Love

Love is about getting the right people in place to solve the problem. Danny Meyer, who started Union Square Cafe and Shake Shack, was once complaining about all the problems his business faced. Someone told him this, and it's advice I come back to often:

"The people who do best in business aren't the ones with the least problems. They're the ones who solve problems better and have more fun doing it with better people."

You're the visionary with the ideas, but the people you bring in carry out the work. Put the right people in the right seats, surround yourself with people who want to solve problems, and your business will move forward.

O is for Operations

If you don't build to scale, you'll never be able to grow. Instagram ran everything on a single computer at launch, and it crashed when people flooded in to sign up. It turned out well for them because of the publicity, but they couldn't have grown on one computer.

Without systems, growth stays limited, depends on you, and feels chaotic. It's better to grow at a pace your systems can support. You can build systems as you go, but know your capacity, and don't overinvest before you've proven demand.

W is for Well-being

Well-being means having the cash to run your business, and cash came up as one of the biggest stressors in these stories. Serena & Lily called their growth a "cash incinerator." Gary Hirshberg, the founder of Stonyfield Yogurt, never knew whether he could make payroll, and he'd call his mother-in-law after his wife went to sleep to ask for another loan.

That stress doesn't have to be there. Plan your expenses around the cash you already have instead of putting the cart before the horse. Profit First is a great system for this. A truly healthy business is a profitable one where the owner takes home real money.

Flourish: Your Business Should Serve You

Flourish is why we do all of this. Paul Orfalea of Kinko's said the business itself should be an instrument to make you happy: you own it, it doesn't own you.

Too many owners I talk to feel stressed, miserable, and trapped by their business. But there's a satisfaction in building something, watching it take off, and seeing your effort rewarded that nothing else can bring. Hamdi Ulukaya, the founder of Chobani, went through five or six very hard years before sales finally picked up. He described it as being in the middle of a soccer game he loved, and said he felt alive for the first time.

As Guy Raz says, entrepreneurship is a mindset about how you approach your work. For me, it's a chance to keep learning and stretching into my full potential.

Then there's the other side. Jensen Huang built Nvidia into one of the most valuable companies in history. When asked if he'd do it again, knowing the pain, the layoffs, and the missed games and birthdays, he said no.

I don't want you to have that regret. Don't sacrifice everything for your business. Build it to serve you, and let your Flow systems help you get there.

Your Next Step This Week

Write down one hard thing you've been gritting your way through. Then work through it in three steps:

  1. Focus: Remind yourself why you're doing it.

  2. Flow: Set up one system that makes it easier, so you're not relying on willpower alone.

  3. Flourish: Define what success looks like for you. How should your business support your life?

If you left for two weeks tomorrow, what would break? If you're not sure, or you're afraid you already know, take the free Two-Week Vacation Test. In a few minutes, it shows which parts of your business still depend on you and where your growth is leaking, so you know what to fix first.

Business doesn't have to be this hard. Until next time, may you find your flow.

Cordes Lindow
Cordes Lindow helps trade and service founders build the systems, culture, and metrics needed to pass The Two-Week Vacation Test, unlock real exit value, and scale past the owner bottleneck.
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A note on how this was written: This article was created with AI from the transcript of this week's episode of Mastering Business Flow. The transcript is not AI-generated. It's me, talking through my own ideas, experiences and thoughts on each topic. AI helped turn my spoken words into a more organized, readable article, keeping as much of my original language as possible.

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