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Should you make your first hire? My experience almost 1 year in

By May 19, 2022No Comments4 min read

Before welcoming the first full-time hire to the team in June 2021, I spoke to a lot of people asking for their general advice around the subject.

Some said:
“It was the best thing I’ve ever done. I can’t imagine not having a team.”
“It’s a no-brainer”

Others said:
“It turned into a nightmare situation for me involving legal cases.”
“We had scaled up to 15 employees, then had to let them all go after the crash. It was such a harrowing experience that I will never hire again.”

From these conversations, it was hard to draw a clear conclusion about what the best move was for As always, the right path is incredibly nuanced and varies from situation to situation.

Deciding to Proceed

After having all of these conversations, I decided to proceed for a few key reasons:

1) there was excitement in the thought of growing a team

2) a great relationship had formed between the hiree who had freelanced with me for almost a year until that point (Kier)

3) the company was growing and needed to be invested in to maintain high standards of service and high quality of output

How has it changed things?

Becoming an Organisation

When transitioning from solopreneur to an organisation, there are a lot of new questions to consider. To name but a few:
– what specific processes does your company follow? You can no longer just wing it alone
– how do you want your company culture to be? There will always be a company culture at play whether you define it or not
– should you be a remote company or not?

My approach has been to address these things as they arise so as not to get too overwhelmed initially. Envisioning how this organisation will evolve over time is now a really fun part of the journey.

Long-Term Commitment

Previously, I liked the noncommittal nature of being a solopreneur. If you became fed up with your business, you could wind down relatively easily and move on to pastures new.

Before deciding to build an organisation, you have to commit to a mindset change.

This mindset change involves going from a short-term, noncommittal mindset to a long-term, very committed mindset. The more committed and long-term focused you are, the more those around you in the organisation will be too (I hope!).

It’s only in the last year of growing an organisation that I have become excited about the thoughts of growing this business for decades to come.

In the words of Warren Buffett “In a crazy way I look at Berkshire as a painting, and it’s unlimited in size.”

Increased Aspirations

As the organisation grows, your aspirations for the future grow too.

Naturally you envision more people in the organisation. But you also begin to dream about how high-quality and transformational your service could be.


Committing to growing an organisation can be daunting.

Going from 1 person to 2 people is also probably the largest % increase in team size your organisation will ever undergo in a single move (100% increase).

My only advice would be to ensure that:
– your first hire is going to be value add to the organisation
– you’re ready to commit long-term to growing the organisation
– you’re doing this because you want to, not just so you can tell others that you’ve made a hire

And most of all, good luck!

Thank you for reading,