Once upon a time, I was a great fan of the design show Project Runway. Judge Tim Gunn was known for his mantra, “Make it work!” No matter how dire the status of the designer’s project, Tim would remind them that naked models were not allowed on the runway.

As entrepreneurs, we figure stuff out. We operate on shoestring budgets. We make a lot of tradeoffs. We see a challenge and believe in ourselves to figure it out. We have can-do attitudes and optimism. We’ll work around the clock to make sure we do not send naked models down the runway. 

We know the conditions will never be ideal. But I often wonder, are we too good at making it work? 

The internal conversations sound like this:

Should I take this deal? Yeah, I can make that margin work. I can take on the extra five hours of work. I can skip my workouts and work on Saturday mornings. 

Should I hire or fire this person? I can try harder, work around their weaknesses, take a pay cut, bring in a coach. 

Should I cut my pay? I can tighten my belt, reduce my retirement savings, skip the health insurance. 

I can try harder. I can endure more. I can live with less. 

Despite the stories you see celebrated in the press and movies, you are not destined to push things as far as they could possibly go in order to succeed. When, as an entrepreneur, should you let something go? 

Watch and listen for these signals:

• It violates your core principles or pillars. 

• You’ve exceeded the self-imposed time box.

• Your gut and/or brain are screaming no. 

• It’s out of scope and you’re quiet overdelivering. 

• You feel physically or mentally unwell.

• You don’t want to. 

• You cannot meet your basic needs. 

You are allowed to say no. That’s not a fit for us. We’re not taking new clients at that level. I don’t work on Fridays. 

You can have entrepreneurship and boundaries. It feels weird, it’s not super common, but it is absolutely okay. 

What boundaries are non-negotiable for you in your business? How do you maintain them? Hit reply, I’d love to hear from you.

Media Kit 

Chicago Booth Review Podcast: Do you feel treated fairly? If not, have you used that to justify bad behavior? Research by Lucia Annuzio from focus groups in 28 countries shows that feeling unfairly treated can lead to resentment and even sabotage. This podcast explains why people feel justified in stealing money, shipping defective products, lying to customers, faking results, and other outcomes you probably want to avoid in your company. 

Time Magazine: I hate checks. I don’t use them and I work hard to design financial operating systems that eliminate them. The US banking system finally has my back. A new structure for instant payments is rolling out across banks and credit unions that will finally eliminate the need for personal checks. Your bank might use these “rails” to facilitate Zelle, or as its own service. Great article for understanding the evolving options for moving money. 

WSJ: If you have a business partner, or a family business, you may be advised to get a type of life insurance called key person or buy/sell. This is a common succession planning strategy for small businesses, because life insurance proceeds are not taxable. Or rather, they were not. In a 9-0 decision, the Supreme Court sided with the IRS to eliminate buy/sell tax savings. If you are using life insurance in buyout or succession planning, talk to your financial or tax advisor. Here’s a version from Forbes not behind a paywall. 

The Information: is it better to start a consumer or business-to-business company? It’s generally been understood that the potential for enterprise or B2B companies is better than those focused on consumers. But VC firm Forerunner Ventures recently published an analysis of 7,800 start-ups that showed consumer investments outperform B2B  in terms of growth and exit potential. Something to think about in your 2025 planning.