This newsletter is about a trap I see all the time in high performers trying to build a side business: over-preparing, overthinking, and overanalysing before they take any real action. What looks productive on the surface is often the very thing keeping them stuck. And in the early stages of building a side business, that habit can cost far more than people realise.
When I first started my online fitness coaching business in 2020, I spent an entire weekend building a website and a library of workout programs.
At the time, it felt exciting, even productive. It gave me that satisfying sense that I was finally doing something real.
And in my mind, I had a perfectly reasonable explanation for it: if I wanted to look legitimate and professional, surely I needed a proper website and a bank of workout videos ready to go.
A month later, the website still looked good. The workout programs were sitting there. But I had no clients.
The problem was not that the website was bad, or that the workout library was poorly done. The problem was that neither of those things addressed what my clients actually needed.
What they needed was help with mindset, with consistency, with habit formation. They did not need another set of exercises to start; they needed support to stop falling into the cycle of stopping and restarting.
What I had built was a very polished answer to the wrong problem.
And I had built it in complete isolation.
This Is Not a Story About Being Unprepared
What makes this pattern so interesting is that it usually does not come from a lack of discipline or seriousness. In fact, I often see the opposite.
It is often the high performers who fall into this trap. Women with successful corporate careers. Women who are capable, conscientious, and used to producing a high standard of work. Women who know how to think things through and get things done properly.
Those are also the women most likely to spend three months researching their niche before speaking to a single potential client. Most likely to rewrite their offer several times before testing it once. Most likely to feel, quite sincerely, that they are making progress when in reality they are still preparing.
Corporate Conditioning Has a Hidden Side Effect
In the corporate world, thoroughness is rewarded for good reason. You do not go into a board presentation with a half-formed idea. You do not propose a strategy you have not pressure-tested. You do not move until you have enough information to defend your position.
This is part of what makes someone effective in a corporate environment. It protects you, your team, and the organisation from making costly mistakes.
The problem is that this same instinct can become unhelpful in the early stages of building a business.
Because business does not always give you clarity first and action second. More often, it works the other way around. You take action, you get feedback, and that feedback gives you the information you need to refine the next step.
That is a very different loop from the one most corporate women have been trained in.
Why Over-Planning Feels Productive (But Delays Proof)
After working with and talking to many senior corporate women, and hearing how they describe their side business journey to me, I hear the same pattern in different forms.
They have spent weeks, sometimes months, researching. Listening to podcasts. Reading books on positioning. Studying other coaches’ websites. Taking notes. Filling out workbooks.
And when I ask how many people they have spoken to about their idea, the answer is usually: none.
Research feels like progress because, in many ways, it does resemble progress. It takes effort. It produces something tangible. You have notes, frameworks, refined thinking, and clearer language. It feels as though you are building something of value.
And to a point, you are.
But what you are building at that stage is still a theory about what people need. Until that theory is tested against real conversations and real buying behaviour, it is still only that: a theory.
I built workout programmes for people who needed help with their mindset and consistency. My theory was logical. My execution was thorough. My research was complete. And I was solving a problem that did not rank highly enough for anyone to actually pay me to fix it. What my fitness clients needed was not a better workout plan. They needed help changing the habits and behaviours that were keeping them stuck.
The Difference Between Treating Your Business as an Experiment and a Permanent Decision
One of the most useful shifts I made in my own thinking was to stop treating every early business decision as if it needed to define the next five years of my business.
At the beginning, you are not making a permanent decision. You are running an experiment to see whether an idea has traction. That experiment might last 90 days. It might last 12 months. But it is still an experiment.
That distinction matters more than it seems.
Because when something feels permanent, we instinctively prepare for permanence. We want certainty before we move. We want every angle covered. We want to know that we are not making the wrong call.
But when you see it as an experiment, the pressure eases. The goal becomes learning, not perfection, and permission to act becomes much easier to grant yourself.
What Testing Actually Looks Like
For a corporate woman building a coaching or consulting offer alongside her career, testing does not require a website, a logo, a business name, brand colours, or a fully mapped client journey.
What it does require is a clear way of explaining who you help, what problem you believe you can help solve, and what kind of transformation or outcome someone might reasonably expect from working with you.
And all of that requires having real conversations with real people who might actually pay you.
Those conversations matter because they tell you things that desk research cannot. What someone is genuinely struggling with, what they have already tried, what frustrates them, what solving the problem would actually mean in their life – that kind of information sharpens your thinking far more quickly than another week of solitary analysis ever will.
Once you collect enough data, you then analyse it, assess the gap, and decide how to pivot. That is how you move a side business forward.
There is one more part of this that I do not think gets talked about enough: this stage should not drag on indefinitely.
I have seen people spend far too long here, going back and forth between niches, changing the ideal client, tweaking the messaging, having more conversations, then circling back to change everything again. At some point, that stops being useful research and starts becoming another form of delay.
This is why I think it helps to put a timeframe around it. Give yourself no more than two weeks. Speak to five to ten people. Gather what you need, look at the patterns, and then move on.
Final Thoughts
High performers do not usually stall because they are incapable of building a business. More often, they stall because they have been trained to reduce risk before they act, and they have not yet adjusted to the reality that in early-stage business, action is often what reduces risk.
Looking back, I should have spent that weekend talking to people instead.
Not building a website. Not creating programs. Just asking better questions and listening.
I would have gotten to the real problem much faster.
So maybe that’s the question to sit with this week: where are you still building before you’ve really listened?
And if part of the reason you stay in preparation mode is because time already feels tight, you may find this helpful too: You Don’t Have a Time Problem. You Have a Structure Problem.