Who develops you when you’re the boss? Why learning matters for startup founders

Going it alone takes courage. Whether you’re leaving a secure job, launching a business or taking on your consultancy role, there comes a point when you have to back yourself before you feel entirely ready.

I know that feeling. I’ve spent more than 20 years working as an employee within HR and people development roles within organisations, helping leaders navigate change and grow into their roles. But, when I set up my own leadership development and coaching business, Optability, in 2023 I experienced a few identity stumbling blocks.

On paper, I was a business owner. In my head, it took longer to feel like one.

That gap between the role you’ve stepped into and how you see yourself is something I call The Identity Gap™. And it’s particularly relevant to start up founders, who often have to become a different kind of leader as their business grows.

When you’re employed, there are often structures around your development. You might have an annual appraisal, a training budget, a manager who encourages you to take a course or a clear progression route to follow. When you go it alone, those structures tend to disappear.

Nobody necessarily asks what you’ve learned this year, what skills you need to develop or where you want to be in five years. You’re responsible for finding the work, looking after clients, managing the money and keeping the business moving.

And. truthfully, professional development and continued development, can quickly slip down the list of ‘to-do’s’ – because, there are invoices to send, proposals to write and a dozen other things that feel more urgent.

But, just because nobody is arranging your continuing professional development (CPD) doesn’t mean your learning has to stop.

In fact, building a business makes learning even more important. Your business will change, your responsibilities will grow, and the person you need to be to lead it will change too.

The challenge is that development isn’t always about acquiring another qualification or adding a certificate to your LinkedIn profile. Sometimes, it starts with looking at yourself.

The business can grow faster than your self-image

Early in my career, I was promoted to lead a team of people who had previously been my peers and friends. I knew the job and understood the team, but suddenly I was responsible for having different conversations, making decisions and holding people accountable.

I was trying to be one of the team and the boss at the same time. The job had changed, but how I saw myself hadn’t caught up.

I experienced something similar when I became self-employed. Making the decision to set up a business didn’t automatically give me the confidence or identity of a business owner.

I see this pattern in founders, too.

You might launch your business because you’re brilliant at what you do. But being a talented designer, consultant, accountant or specialist doesn’t automatically prepare you to sell your services, make difficult decisions, delegate to employees or lead a growing team.

As the business develops, you have to develop with it.

If you still see yourself as the person who has to do everything, delegating can feel uncomfortable. If you believe you need to keep everyone happy, setting boundaries with clients might feel impossible. And if you don’t quite see yourself as someone who belongs in the room, you might hold back from opportunities you’re perfectly capable of taking.

These aren’t necessarily skills problems. Sometimes, they’re about the beliefs and habits that shape how we behave.

Feel the fear and do it anyway

I’m a firm believer that you don’t have to wait until you feel confident to take the next step.

We can spend a long time preparing to become the person we want to be. We can buy the books, book the course, research every possible outcome and tell ourselves we’ll start when we feel ready.

But readiness doesn’t always arrive first. Sometimes, you have to do the thing while you’re still nervous. Put yourself forward for the opportunity. Have the conversation you’ve been avoiding. Charge what your work is worth. Ask for help. Admit you don’t know something.

Each time you do, you give yourself evidence that you can handle more than you thought.

This doesn’t mean ignoring genuine risks or throwing yourself into every opportunity. It means recognising the difference between a sensible reason to wait and the discomfort of doing something unfamiliar.

As founders, we’re often so focused on building the business that we forget we’re building ourselves alongside it.

Make your development part of the job

So, how do you keep developing when nobody else is responsible for making it happen?

First, be honest about where you are now. What comes naturally to you, and what are you avoiding? What does your business need from you at this stage, rather than the stage you were at when you launched?

Second, make time to learn. That might mean formal CPD, coaching, mentoring, reading, networking and conversations with other founders or getting feedback from someone who sees your blind spots. Not every lesson needs a price tag or a certificate, but it does need your attention.

So, your next stage starts with you

Finally, put what you learn into practice. Information alone doesn’t change how we lead. We have to do something differently, reflect on what happens and keep going.

My work through Optability is rooted in behavioural psychology and explores three stages: Stepping In, understanding where you are now; Stepping Out, questioning the beliefs and habits that might be holding you back; and Stepping Up, developing a way of leading that feels both effective and authentic.

You don’t have to become somebody else. You need to grow into the person your next chapter requires and that means dedicating time in your calendar for you.

Your business will change as it grows. You might move from working alone to employing a team, from delivering every piece of work yourself to leading others, or from being the expert in your field to making decisions about the future of the company.

Each stage brings new challenges, and there isn’t a course that can prepare you for every one of them.

What matters is staying curious about yourself as well as your industry.

Feel the fear, take the next step and keep learning along the way.

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