Self-Employed Most Businesses Are Scaling the Wrong Things. Here’s What to Actually Build Read the Article Open Share Drawer Share this: Share on Facebook (Opens in new window) Facebook Share on X (Opens in new window) X Share on LinkedIn (Opens in new window) LinkedIn Share on Pinterest (Opens in new window) Pinterest Print (Opens in new window) Print Written by Alex Leiberman Published Sep 9, 2026 4 min read Everything you say yes to is something else you’re saying no to. When business owners say they’re “scaling,” it usually looks like one of two things. They’re hiring more people to handle the chaos Or they’re launching more initiatives — new products, new channels, new bets everywhere Both feel like progress on the surface. And a lot of the time, both quietly make the business worse. Your refund is waiting Get started At Morning Brew, we learned this the hard way. For the first four years, we were relentlessly focused on one thing: a daily email newsletter. That focus built the foundation of the business. Then, we started doing too many things at once. We explored YouTube. We launched podcasts. And we ended up hiring too fast, cycling through a handful of key leaders before we found the right fit. Ambition wasn’t the problem. Unfocused ambition was. Growth is easy to fake. Real scaling is uncomfortable. It means cutting what doesn’t work before it’s obvious to everyone. It means systematizing before hiring. It means asking whether your people are doing only the work they can do. The hiring trap nobody talks about Most founders hire to fix broken processes. Sales are down, so they hire reps. Data is messy, so they hire analysts. Customer service is slow, so they hire support. It feels logical, but what actually happens? Margins shrink as revenue grows. You’re not scaling. You’re spending more to stay in place. A simple rule of thumb: If you can clearly explain how a role works step-by-step, there’s a good chance that at least part of it can be automated. There’s a whole class of routine cognitive work — data analysis, information retrieval, customer service, sales outreach, CRM updates, even standard content creation — that’s moving from “hire a person” to “build a process.” Take sales as an example. Most salespeople don’t spend the majority of their time building relationships with customers. They spend it on follow-ups, updating the CRM, researching leads and doing admin work. So the opportunity cost is huge. Every hour spent on repetitive tasks is an hour not spent building trust with clients, and that’s the part we can’t automate no matter how good the tech gets. How to actually build something scalable At Tenex, we talk about becoming a cartographer of your company. In other words, building a clear map of how work actually gets done. That starts with understanding your business’s core functions, then talking to the people closest to the work. Find the most AI-open-minded people in each function and make them your champion. Have them walk you through the process step by step so you understand how the work happens today. Then ask a simple question. What is the core process that takes the most human time or costs the most money? And don’t try to rebuild the whole thing overnight. Pick one step that’s: Repetitive Time-consuming And relatively easy to improve Make sure AI can do that step well. Retrain your team on that step, then move to the next one. A good example of this is Vercel. They had 10 inbound sales reps handling leads. One go-to-market engineer shadowed their two best reps for two weeks, mapped the full process, and rebuilt it as an end-to-end AI workflow. They ran it in parallel for a month to make sure performance held up, and then the company shifted those sales reps into higher-value work. That is what real scaling looks like. Not more headcount, but better leverage. Permission to cut So what actually gives you permission to stop doing something? Honestly, it’s almost never a clean moment. Everything you say yes to means you’re saying no to dozens of other things that could create more value for your customers and your business. The longer you keep something alive when every new data point says it’s probably not the thing, the more upside you’re giving up somewhere else. And it’s rarely black and white. One of the hardest parts of being a business owner is getting comfortable living in the gray. If it’s obvious that it’s time to cut something, you’ve probably waited too long. I actually think about this the same way I think about someone deciding to leave a job. The moment most people finally pull the trigger and quit, they’ve usually already spent months — sometimes way too many months — being unhappy, unfulfilled, and closing off other opportunities that could have been better. The decision that felt scary to make early would have saved them real time and real cost. Cutting an initiative in your business works the same way. So don’t wait for certainty. It’s never going to feel like the perfect time. Once you understand the trade-offs, you’re usually better off cutting a little too soon than a little too late. The goal of scaling is not a bigger org chart. It’s the same people doing higher-leverage work. Systems first. Headcount second. If you need clarity on what your numbers actually say while you’re rethinking how you work, TurboTax Experts for Business helps you track income, expenses, and obligations without the manual grind, so you can focus on building what scales. Previous Post The Hidden Tax on Moving Slow: Why the Cost of… Your refund is waiting Get started Written by Alex Leiberman Alex Lieberman is an entrepreneur, creator, and co-founder of Morning Brew. He now leads Tenex, an AI transformation firm helping companies build smarter, more resilient businesses, to win the next decade. More from Alex Leiberman Visit the website of Alex Leiberman. Browse Related Articles Tax Tips Nanny and Housekeeper Tax Rules Life Listen Now: So You’re Buying a Car? Self-Employed Hobby Meets Hustle: Filing Small Business Taxes Work So You’re Crossing State Lines? Taxes 101 Basics of 2010 HIRE Act Self-Employed I’m taking a business trip. What can I write off? Self-Employed Hobby Meets Hustle: How To File Self-Employment Taxes Business Taxes What I Wish Someone Had Told Me Before I Started Scaling My Business Tax Deductions and Credits Writing Off Your Summer: Preparing For Next Tax Season Home Podcast: Are Home Improvements Tax Deductible?