Why working in your business, and not just on it, matters at every stage
Judgement depends on proximity to the work
We’re often told to work on our businesses, not in them. This advice is usually framed as a mark of maturity or scale. But at every stage - including at the top - staying close to the work plays a critical role in judgement, strategy, and risk awareness.
The problem isn’t the advice itself. It’s how easily it’s applied without enough regard for the realities of a small, founder-led business.
Early on, progress depends on fast, unfiltered feedback between decisions and what actually happens. Sustainable progress depends on understanding that reality - not the simplified version popular advice often implies.
Small businesses are far more hands-on than people expect
Running a small business involves far more hands-on involvement than most people expect, and pretending otherwise often leads to bad decisions.
This isn’t a moral claim about effort or ambition. It’s a practical one.
In the early stages especially, there often isn’t enough structure, margin, or clarity to outsource intelligently. You’re still learning what the work actually is, what matters, what’s fragile, and where effort turns into outcomes.
Working in the business is how that understanding forms.
It’s what allows founders to design systems, plan roles, and set priorities based on how the work actually behaves, not how they assume it should.
The biggest cost of stepping away too early: weaker judgement
Underestimating how hands-on a small business will be tends to increase costs, reduce resilience, and weaken decision-making, because the necessary understanding hasn’t had time to form yet.
The most serious cost is weakened judgement.
When founders rely too heavily on second-hand input, they also rely on other people to notice, interpret, and prioritise things that were never really their responsibility in the first place.
This isn’t about staff or contractors doing a bad job. Roles are partial by design. Most people are accountable for a slice of the system, not the whole of it.
Only the founder is responsible for how everything fits together.
When that responsibility is paired with distance from the work, blind spots form early and go unnoticed. Things get missed not because anyone failed, but because no single role is designed to hold the full picture.
Over time, decision-making degrades. Not dramatically - quietly. Judgement stops updating. Leaders become dependent on explanation rather than recognition.
The downstream effects are practical, not abstract
Once judgement weakens, other problems tend to follow.
Costs rise earlier than expected, because work is outsourced before it’s properly understood, roles are mis-scoped, and money is spent on activity rather than outcomes.
Resilience drops, because when something breaks or changes, the founder can’t step in, re-scope quickly, or make informed trade-offs under pressure.
Feedback to staff becomes less specific, because there’s no longer a shared understanding of what the work really involves. Trust can erode on both sides.
And flexibility disappears. When founders don’t know the work well enough to move between roles, even temporarily, the business becomes rigid long before it’s ready to be.
Working in doesn’t mean doing everything forever
This isn’t about avoiding delegation, expertise, or systems.
Hiring people who are better than you at specific roles is almost always a good thing. So is stepping back once things stabilise.
But there’s a difference between delegating execution and outsourcing understanding.
Working in the business, at the right moments, is how founders learn what good looks like, what’s genuinely hard, and what actually matters. That learning doesn’t disappear when you step back. It’s what makes stepping back possible.
The question isn’t whether you’re working in or on the business.
It’s whether you understand it well enough to make good decisions.
Yes, the risks and costs of misunderstanding the work are real - and they’re often invisible until it’s too late.
Originally published at lyndseyburton.com
This piece is part of a notebook on telecoms markets, regulation, complex systems and organisational behaviour.