I was speaking at a client event last month, and someone in the audience asked me a question I wasn't ready for…

❝

"If you could go back in time and be a first-time CEO again…what would you do differently?"

I thought about it for a second, then gave some generic response about "hiring faster" and "trusting my gut." You know…the kind of answer that sounds smart but helps nobody.

It bugged me the whole way home.

So on the plane, I pulled out my notebook and actually thought about what my real answer should have been. Not a polished LinkedIn answer, but a real answer…warts and all.

Here's what I came up with.

1. I'd stop trying to be the best employee in my own company.

I spent years being the “most valuable player” on the team, and all I built was a company that couldn't function without me. (The more valuable you are to your business, the less valuable your business is.)

2. I'd build the business like I was going to sell it…even if I never planned to.

A sellable business is just a business that runs without you. That's it. You don't have to sell it, but if you can't…that's a problem.

3. I'd install an operating system before I hired an operator.

Twice I tried to hire a COO or "integrator" to fix my chaos…and all I got was an expensive executive assistant swimming in the same chaos. First you get an operating system in place, then you hire an operator to operate the operating system. No operating system, no operator.

4. I'd document the 10-20 things that actually matter.

Not 500 SOPs that nobody reads. Just the critical few. The processes that directly touch revenue, delivery, and cash. Everything else is noise.

5. I'd solve for systems first… then people.

The goal isn’t to build a company of “rockstars” and A-players, the goal is to build a company that doesn’t require them. Not only is this the best way to guarantee long-term success, it’s also how you build a company that real “rockstars” and A-players want to work for.

6. I'd build scorecards that mirror the customer journey.

Chasing vanity metrics cost me a small fortune. Impressions, followers, "engagement"…none of it told me where the real bottlenecks were in my business. The metrics that matter track the customer journey from first touch… to purchase… to fulfillment… and everything in-between. If your scorecard doesn’t expose where leads and customers are bottlenecking in your business, you’re measuring the wrong things.

7. I'd set a 3-year goal and execute in 90-day sprints.

Annual planning is just New Year's resolutions for business owners. You set a big goal in January, forget about it by March, and scramble in Q4 to “get back on track.” Three-year goals give you direction and inspiration. 90-day cycles give you focus and execution.

8. I'd stop hiring "helpers" and start hiring functional leaders who own outcomes.

Every time I hired someone to "take stuff off my plate" (but who didn’t have the skills to full own the outcome), I just created more management work for myself (while also having to still do the job half the time). Helpers make you busier. Leaders make you wealthier.

9. I'd fix my margins before I chased revenue growth.

I spent years celebrating top-line revenue while hemorrhaging cash. Turns out a $5M business at 25% margins is worth a lot more than a $10M business with 5% margins. P&Ls lie. Cash doesn't.

10. I'd stop confusing a full calendar with a productive day.

Busy isn't a strategy. Some of my worst weeks were my "busiest," and some of my most “productive” were during vacations when I never opened my laptop or checked email.

11. I'd stop swooping in to "save" things.

Every rescue teaches your team to wait for you next time. I used to wear this like a badge of honor…"Nobody can put out fires like me." All I was really doing was training everyone around me to start fires and wait for Dad to show up.

12. I'd resist the urge to start something new every time something old got hard.

The shiny new project always feels easier than fixing the broken one, but the “broken” one is where the money is…if I’d just stay long enough to fix it.

13. I'd fire problem clients (and problem customer segments) faster.

They always cost more than they pay. Every problem client I held onto too long drained my team, distorted my business model, and delayed the growth I could've had by replacing them with better-fit customers.

14. I'd have the hard conversations 6 months sooner.

Every time I avoided a tough conversation…with a partner, an employee, a client…I paid for it later with interest. Bad news only gets worse with time.

15. I'd remember that my wife and kids don't want my money…they want my calendar.

I don’t have many regrets in life, but the ones I do have are because it took me too many years to learn this last lesson. You can always make more money, but you can't make more time.

I didn't know any of this on Day 1. I learned it all the hard way.

Hopefully you don't have to.

⚡️ Action Step: Pick one lesson from this list that made you wince. The one that felt a little too personal. Write it on a sticky note and put it where you'll see it every morning this week. Not all fifteen…just the one. That's your lesson for right now.

Give it a shot and let me know how it works…

-Ryan

Ryan Deiss
Co-Founder and CEO, The Scalable Company

P.S. I'm looking for 5 business owners who want to work 1-on-1 with my team and me to install a custom "operating system" so your business can scale and so you can exit the day-to-day. Click here for the details.

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