October 9, 2026Why ‘Better Problems’ Are Better Than Perfect Plans

Every business has problems. That sounds obvious, yet most of us act as if the right plan could make problems disappear.

When I sat down with Jason Feifer, the editor-in-chief of Entrepreneur magazine, he handed me a simple idea that changed how I think about problems at work. Stop asking whether a plan is perfect. Ask whether your new problems are better than your old ones.

I’ve been thinking about that shift ever since our conversation. Jason has spent decades in national media, with editing roles at Men’s Health, Fast Company, Maxim, and Boston Magazine, and with writing for The Washington Post, Slate, and New York Magazine. Today he leads Entrepreneur magazine, hosts the podcast Help Wanted, and writes the newsletter One Thing Better. He has watched companies grow, stall, and adapt. And what he keeps seeing is that real progress rarely looks clean. It looks like a fresh set of problems.

We discuss here why that idea matters. It is not about staying positive for its own sake. It is about how we judge decisions, how we talk about trouble, and how we know whether a team is actually moving. The way we think about problems shapes almost every choice we make, and most of us have never examined it.

🎥 Watch and listen to the full interview with Jason Feifer here

The Test That Never Tells You Anything

Most teams judge a new idea by looking for what could go wrong with it. It feels responsible. It feels like good leadership. But Jason points out a flaw in that habit. If you ask whether something is perfect, you will get the same answer every time. As he says:

“If you ask if something is perfect, the answer will be the same every single time. The answer is no, it is not.”

What struck me most is how quietly this trap works. A test that always returns the same result is not a test. It is a ritual. Teams run it, feel careful, and stay exactly where they are. Nobody is lying and nobody is being lazy. They are applying a standard that no idea on earth can meet. I’ve seen this in meetings where a good proposal dies because someone found a flaw. The flaw was real, and everyone nodded. But the flaw was also beside the point, because every option has flaws, including the option of doing nothing.

The real work of leadership is not finding the flaw. It is comparing flaws. That is where the idea of better problems begins, and it is why I believe the way we frame problems matters more than the plan itself. A plan is only as good as the question we ask about it.

Perfection also has a cost that rarely shows up on a spreadsheet. While a team waits for a plan with no holes, the market moves, customers change, and competitors try things. Waiting is a decision. It carries problems of its own, only they are quieter ones, and quiet problems are the easiest to ignore.

Old Problems Stop Feeling Like Problems

Here is the part of Jason’s thinking that I keep returning to. Staying put has problems too. They are just old and familiar, so they stop feeling like problems. A slow approval process, a clunky tool, a customer complaint everyone has learned to live with. After enough time, these things stop registering as trouble. They become the weather.

I think this is one of the most underrated ideas in business. We judge new ideas against an imaginary baseline where everything is fine. But the baseline is never fine. It only feels fine because we’ve adapted to it. The new idea gets all the scrutiny, while the old way gets a free pass. That is not a fair fight. When I read a proposal now, I try to write down the problems of the current way first, as honestly as I can. It changes the room. Suddenly the old problems have names and costs, and the new idea has some company.

This is also a communication issue, and it connects to how leaders talk about change. If people only hear about the risks of the new plan, they will protect what they know. If they hear both sets of problems, they can make a real choice. Honest framing builds trust, and it gives a team permission to say that the old way hurts. If you want to go deeper on this side of the story, the communication topic page is a good place to start.

I’d add one more thought. Familiar trouble is expensive because nobody budgets for it. A new problem arrives with a clear price tag and a deadline. An old problem bleeds time and energy in small amounts for years. When we compare the two, we tend to compare a vivid cost with an invisible one, and the vivid one always loses.

Trading Problems Instead of Avoiding Them

Jason’s question is simple. Is my new problem better than my old problem? It sounds small, but it swaps a goal that can’t be met for one that can. You can’t avoid problems. You can only choose which ones to carry. If a new approach trades a problem you’ve lived with for one that is easier to deal with, that counts as progress, even if it’s messy.

I like how honest this is. It does not promise a clean outcome. It promises a better trade. Picture a restaurant that moves from a cramped kitchen to a larger one. It will have new problems: higher rent, more staff to manage, more to lose if it fails. Nobody should pretend those are small. But they are the problems of a business that has outgrown its first kitchen, and most owners would take them gladly. The old problems were a ceiling. The new problems are a floor to build on.

That example is mine, not Jason’s, but I think it shows the logic. The point is not to be happy about trouble. The point is to ask what kind of trouble you want. Some problems drain you and teach you nothing. Others stretch you and point somewhere. Over time, the quality of your problems says a lot about where you are headed.

There is a quiet kind of relief in this view. When you stop expecting a decision to be free of cost, you stop being surprised by the cost. You can plan for it, talk about it, and even make peace with it. A team that has agreed in advance on the trade it is making is much harder to rattle when the bill arrives.

What New Problems Tell You About Growth

One of the most useful shifts in this conversation is how Jason reads trouble. New problems at each stage of growth usually mean the old ones got solved. A company that has never hit a new kind of problem probably hasn’t moved. I wrote that down twice while we talked, because it turns a common source of stress into a piece of evidence.

Think about what that does for morale. Most teams treat a fresh crisis as proof that something is broken. They get defensive and look for someone to blame.

But if new problems are a sign of motion, the same crisis can be read in a different way. It might mean the last stage worked. The inbox is overflowing because readership grew. The hiring crunch exists because demand rose. The problems are a receipt for progress, and a receipt is something you can be glad to hold. Jason says it on stage this way:

“To create problems is to be fixing things, is to be moving things forward, is to be leaving the old problems because we’ve solved those and we’ve gotten ourselves into an entirely new batch of problems.”

I find that line worth reading twice. It treats problems as a byproduct of fixing things. You can’t have the second without the first.

This is also where I’d connect the idea to business growth. Growth is not a straight line of wins. It is a chain of problems, each one a little more interesting than the last. If your problems have not changed in two years, that is worth noticing. It may be a sign of stability, but more often it is a sign of a stall. The healthiest companies I know are not the ones with no trouble. They are the ones whose trouble keeps changing shape.

How This Plays Out Inside a Media Business

Jason shared how this mindset works inside Entrepreneur magazine, where he faces new challenges every day. I’ll stay with the principle rather than the details, because the principle travels well. Media is a hard place to practice this idea because the ground keeps shifting. Audiences move between platforms, formats change, and a strategy that worked last year can feel stale by spring. A leader in media cannot wait for a perfect plan, because the plan would be out of date before anyone approved it.

That is the setting where better-than-before thinking earns its keep. A team that runs a magazine, a podcast, a newsletter, and a community is always trading something. Time for reach. Depth for speed. Focus for experiments. Each trade leaves a gap somewhere else. Jason has a view of this from many angles: print, digital, a podcast downloaded a million times a month, and a newsletter read by 80,000 people. When you have worked across that many formats, you stop expecting any one of them to be finished. You learn to ask what the next version solves.

What I find most interesting is the emotional side. Running a brand that people watch closely invites a fear of being wrong in public. The question of better problems gives a leader a way to act without claiming certainty. You can say, we are not sure this is right, but we believe its problems are better than the ones we have now. That sentence is honest, and it keeps people moving. It also makes it easier to change course later, because nobody promised that the plan was flawless.

Innovation Needs a Lower Bar for Starting

People often talk about innovation as if it were a talent. I’ve come to see it more as a standard of proof. If an idea has to be perfect before it is allowed to begin, almost nothing new will ever begin. Innovation starts when a team agrees that a better set of trade-offs is enough to justify a try.

This does not mean being careless. Jason’s question is a real filter. It asks you to describe the old situation and the new one with equal honesty, then compare them. Many ideas fail that test, and they should. Some trade a problem you can live with for one that could sink you. The value of the question is that it makes the comparison visible. A bad idea has a harder time hiding when you have to name what it costs.

I’ve also noticed that small tests make this easier. A pilot, a trial month, a limited launch. These lower the price of being wrong, which lowers the pressure for a perfect plan. You are not betting the company on the idea. You are checking whether its problems turn out to be the ones you predicted. And when they aren’t, you’ve learned something real, which is often worth more than the result you hoped for.

Leaders Set the Standard for Trouble

In the end, this is a business leadership idea. The way a leader reacts to trouble sets the rules for everyone else. If a leader treats every setback as a failure, people learn to hide setbacks. If a leader treats a setback as a sign that the team has moved, people bring it up early. Early is when problems are cheap to fix.

I’ve seen both kinds of rooms. In one, people soften the bad news, and the leader finds out late. In the other, people say, here is our new problem, and here is what we left behind to get it. The second room is calmer, and it is also faster. It is not that the people there have fewer difficulties. They simply share a language for talking about them, and that language removes a lot of fear.

That language matters for business results too. Teams that expect new problems spend less energy on surprise and more on response. They also tend to keep their ambition. A team that fears problems shrinks its goals until nothing can go wrong. A team that expects them can aim higher, because it already knows what to do when the next batch arrives.

Questions Worth Asking Before Your Next Decision

I want to make this practical, because an idea like this only matters if it changes what we do on Monday. Start with the decision you have been putting off. Write down the problems of staying where you are, in plain words and with real costs. Then write down what you expect on the other side. Put the two lists next to each other and read them as if they belonged to someone else.

Then ask the plain question. Is the new problem better than the old one? Better can mean cheaper, smaller, easier to fix, or more useful to learn from. It can also mean it points toward something you want. Be honest about the answer. Sometimes the old problem really is the better one, and staying is the right call. The goal is not to push change for its own sake. The goal is to choose with open eyes.

After that, look at the problems you’ve already left behind. This step gets skipped, and I think it is the most motivating one. Most people carry a long list of current frustrations and no record of the ones they’ve outgrown. Write that second list. If you started a company, think of the trouble you had before your first customer. If you grew a team, think of what it was like when it was only you. That record is evidence of progress, and every entrepreneur I know tends to forget it.

Jason’s idea leaves me with one last question. If you traded your biggest current problem for the one waiting on the other side of the decision you’ve been putting off, would you come out ahead? If the answer is yes, the plan does not need to be perfect. It needs to be better.

Choosing the Problems You Want to Have

When I look back at the conversation, the thing that stays with me is how freeing it is to stop chasing perfect. Perfect was never on offer. What is on offer is a choice between sets of problems, and the people who keep moving forward are the ones who learn to choose well.

The lesson is not that problems are good. It is that they are information. The old ones tell you what you’ve outgrown. The new ones tell you where you are heading. A leader who can read problems this way becomes calmer, clearer, and braver, and so does the team around that leader.

So the next time a plan fails the test of perfection, let it fail. Ask the better question instead. If you want to bring this thinking to your own team, you can learn more about Jason Feifer and his work. And then pick the problems worth having.

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