28. Stop Planning, Start Experimenting: A Better Way to Build Your Business

You want to start or grow your business the “right” way, so naturally you look for a solid plan to get started. More data and more certainty should mean less risk, right?

The problem is that we often cling to plans and data to create an illusion of control, even though business (much like life), is wildly unpredictable. The result is analysis paralysis, delayed momentum, and a business built around theory instead of real results.

In this post, I want to flip that thinking on its head. I will share why the most successful businesses are not built from perfect plans, but from experimentation, and how taking action, running small tests, and letting the market guide you can actually reduce risk rather than increase it.

Why planning feels so comforting when starting a business

At the start of every year, I tend to notice the same pattern. January rolls around, inboxes wake back up, and I start having a lot of conversations with people who are thinking about starting or growing a business and want support to do it well.

In many of these conversations, I hear the same request phrased in slightly different ways. People want two things from me. They want a solid plan, and they want data, analysis, and evidence that will help them feel confident they are making the right decisions.

On the surface, this makes perfect sense. Starting a business is scary, especially if you are walking away from employment where someone else is responsible for making sure you get paid on time. When you run your own business, that responsibility sits squarely with you, and it is only natural to want to de-risk the process as much as possible.

The challenge is that planning and data can easily become a substitute for action rather than a support for it.

Why plans rarely create certainty in the real world

I often use a simple analogy to explain this. Think about hiring a plumber. You do not choose a plumber based on a detailed plan of how they intend to fix your pipes. You hire them because they can stop the leak. The definition of success is clear, and the expert adapts as they go based on what they find once they start working.

Business works much the same way, so why do we expect it to be far more predictable?

When clients tell me they want a detailed plan before they begin, I usually explain that I do not create traditional business plans. In my experience, plans are useful for business school assignments, loan applications, and case competitions, but they are not especially useful for building a real business in the real world.

Even investors rarely rely on business plans. They look at pitch decks, real traction, customer validation, and financials that reflect what is actually happening rather than what someone hopes might happen.

Great plans do not predict who your actual customers will be, how they will behave, or what they will value most once you start offering your service.

The problem with building from theory instead of feedback

The traditional model of building a business goes something like this:

You come up with an idea, you build the product or service, you market it, and then you hope customers show up.

This approach is also why so many startups fail. It is built around the founder’s vision rather than the customer’s reality.

What changed everything for me was discovering the Lean Startup model, which flips this process on its head. Instead of building in isolation, you validate your assumptions early and often by engaging with real people in the real market.

The process looks more like this:

• Start with an idea and test it with potential customers
  
  
• Use their feedback to build a simple version of your offer
  
  
• Put that offer back into the market and gather more feedback
  
  
• Adjust, refine, and iterate as you go
  
  

This approach is far less theoretical and far more experiential, and it gives you real data that actually matters because it is grounded in behavior rather than assumptions.

Why experimentation actually reduces risk

One of the biggest misconceptions I see is the idea that experimentation is risky and planning is safe, when in reality the opposite is often true.

When you run small experiments, you limit downside while increasing learning. You are not betting everything on one big idea or one perfect model. You are testing assumptions one at a time and letting the market respond.

This also applies to how you experience running your business. Experimentation allows you to discover not only what your customers want, but what you want as a founder.

You get to ask yourself questions like:

• Do I enjoy delivering this service in this way
  
  
• Does this business model fit the life I want to build
  
  
• Is this profitable in a way that feels sustainable
  
  
• Does this work energize me or drain me
  
  

Those answers rarely come from a spreadsheet. They come from doing the work.

A personal lesson from my own life

I often think about this in the context of giving birth. Like many first-time mothers, I created a very detailed birth plan, believing that planning would help me avoid disappointment and reduce risk.

What I eventually learned is that there are many versions of a successful birth. The real definition of success was a healthy baby and a healthy mother, not whether everything unfolded exactly as planned.

What mattered most was having a team around me who could adapt in real time as circumstances changed.

Business is no different. There is no perfect plan that can account for every variable, and trying to control every outcome often creates more stress, not less.

Data still matters, just not in the way you think

To be clear, this is not an argument against data. I am incredibly data-driven in my work with clients. We look at patient volume, collections, financials, and performance metrics because those numbers provide real feedback.

The difference is that this data comes from action, not speculation.

Data inside a business plan is usually based on averages, projections, and assumptions from the outside world. Data from running experiments reflects what is actually happening in your business, with your customers, in your market.

The real way to de-risk your business

If there is one takeaway I want you to walk away with, it is this:

The best way to reduce risk and increase your chances of success is not to plan harder, but to act sooner.

Take one assumption, test it, gather feedback, adjust, repeat.

Momentum, community, and learning how to think like a CEO all increase your odds far more than waiting for certainty that never truly arrives.

Starting and building a business is a creative act. There is no single recipe, no universal blueprint, and no perfect plan that guarantees success. There is only the willingness to begin, to experiment, and to learn as you go.

Listen to the full episode to hear more about this approach to building a business through experimentation instead of perfect planning. And if any of this resonates with you or sparks questions about your own journey, I'd love to hear from you at [email protected].