Q49: How Do I Decide Whether and When to Expand?

“I am freelance and have been for 20 years but I wonder if you have any advice about knowing when to stick with freelance or move to expand, possibly using associates. I really like the freedom of being freelance but I sometimes wonder if I am leveraging my skill set enough.”

This is a fascinating conundrum.

I’ve been freelance, self-employed, a business owner, a director of a limited company, and a partner in a business. I think I have tried on every variety of working for myself that exists. Mostly, they aren’t better, they are just different.

No, I lie. Today the one I like best is just being me.

However, let’s take yours at face value, starting with the point you make at the end.

You wonder if you are leveraging your skill set enough. OK, only you can decide this, always remembering that there’s no requirement to do everything of which we are capable.

For instance, people say I would have made a great mother. I’m not so sure myself. But either way, I didn’t go that route.

I was an excellent county-level swimmer. I might have trained for something superhuman like say crossing the English Channel to France. But I did not.

Did I have the capacity for either of those in me? Probably. Do I care that I haven’t done either of them and explored my possibilities to the max? No.

So that’s what I mean by only you can decide. There’s no requirement to do that. And it will be different and bring new challenges, which you might like more or even less.

You say you like the freedom of being freelance. Quite. I do too. It is strangely addictive knowing that you don’t have to take any or all the work that comes to you, knowing that it is always your choice is very liberating. But what about if you had other mouths to feed in your biz, as it were? Would it feel so good or would there be compromises involved?

The reasons for expanding, possibly using associates, would be to make more money for less personal effort in delivery. But you might need to work just as hard in other directions. Finding work to feed those associates, as inferred above. So is that work you would relish for a change? Building your brand, taking on and managing projects, taking on and managing and training associates?

Managing. Managing. Managing. I’ve done that and I didn’t like it as much.

Could you experiment and see? I don’t think there’s a knowing in advance, except in your gut. My knowing came from doing and I didn’t like it as much as being on my own and when I work with clients who have staff and associates, there’s a lot of frustration which goes along with that.

That in itself is not a reason not to experiment.

How about a pros and cons list, for starters? You are quite process-orientated, I know that about you. Draw up reasons for doing it and against doing it and measure them.

I think probably the main reason for doing it would be because your desire for change and challenge outweighs how much you enjoy your freedom. I think you must be experiencing a sense of that otherwise I don’t think the question would have occurred to you to ask at all. Am I right?


  • What are the joys of working in the way you currently do?
  • And the restrictions?
  • On a scale of 1-10, how ready are you for a change or a challenge?

Your Biz Your Way

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