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Navigating the highs and lows of self-employment

Navigating the highs and lows of self-employment
Opinion

More people are choosing to become their own boss. From finances to the variety of roles on offer, here are some lessons I’ve learned on my own journey.


With redundancies across media land continuing to be a feature this year, more and more people are joining the ranks of self-employment.

It’s a big brave step with many rewards, but equal amounts of challenge. I’m still only two and a half years in and have lots to learn, but here are some of the things I have picked up along the way.

Accept the pitfalls

Self-employment is the ultimate in flexibility and autonomy — you are your own boss and can decide when and how you work. This spans everything from working hours to the types of clients and briefs you take on.

I have turned down work that doesn’t match my aspirations and values — it is scary, but ultimately it helps you save space for work that is more rewarding.

For me, self-employment has delivered the ultimate empowerment, allowing me to define my own destiny. There have been times when I have worked flat out and stretched myself, and times when I’ve decided to take a break and focus on things outside work.

These benefits come with a side order of financial uncertainty — this is the biggest challenge and the main reason why people go back to salaried work. It is famine and feast, and you need to be prepared for this. It’s a mindset change in terms of acceptance of risk and the sooner you can squirrel away a buffer, the better.

Another common stumbling block is not being prepared for the stretch. You will be your own marketing, finance, admin, new business, IT and HR department. There is a ton of work you need to do that you can’t invoice. Being ambidextrous and prepared to learn or pay for support is essential. You also need to set project or day rates that allow you to account for these tasks.

There are lots of ways to do it

Most people enter self-employment with a vision that they might freelance for a while or an ambition that they want to build their own business.

The truth is the range of options is much more diverse. There is project work, retained work, temporary cover and maternity roles, non-executive director opportunities, fractional roles; you can be a sole trader or set up your own company.

Some people go in alone; others partner up; some do both. Some find their own clients; others use third parties and platforms like YunoJuno, Liberty Hive and TheZoo.London.

My advice: don’t give up too quickly and get tempted back to a full-time job. First ensure you have fully explored a range of these options.

Don’t hurry to define your offer

It’s tempting when you launch to invest a lot of time defining your offer. I’ve seen some people do this successfully, but others take their time to find the work and evolve to fit market needs.

Start by catching up with your network and reminding everyone what you are good at. You’ll be surprised how quickly this can create momentum and your offer naturally evolves from this.

I think it’s actually more important to do work on your personal brand than your company brand. This will ensure you do the work you love and guarantee job satisfaction.

Let go of old ways of working

After working nine to five for years, it’s easy to fall back into the same habits. Take time to think about the type of working day/week you want to have. How much time do you want to be at your desk versus out and about? What times of day do you want to work? How much holiday do you want to take?

There is much more scope to give yourself a sabbatical or work from abroad, and self-employment is a great model for early birds, as well as parents doing the juggle.

Get clued up on finances

It’s a bit scary being in charge of your own accounts, but a good accountant will help you out with the essentials. Talk to other freelancers and check out these brilliant guides from Matthew Knight, who is an amazing self-employment advocate.

I also recommend taking a good look at your household finances and asking yourself how much you really need to earn — set a baseline for the standard of living you want. Remember, you may be able to save money on commuting and, depending on your circumstances, you could end up paying less tax.

It’s not just about the content — it’s the connections

Sitting at home with the pressure to generate leads and in a climate that defaults to social media, you can end up spending a lot of time posting content. While keeping up your presence is key, it’s also important to make connections and build relationships.

Most of my new business has come from face-to-face meetings — just because that’s what I enjoy the most. Remember: you get to decide. Furthermore, social media can be as much about a dialogue as it is a broadcast channel for B2B marketing.

Keep your pipeline in mind

It doesn’t matter whether you chose to market yourself face to face or on social media; it’s essential that you always keep your pipeline in mind.

Even when you’re fully booked up for the next few months, speculative coffees or social presence will ensure that the opportunities keep coming. It often takes a while for a new client to convert, so you need to think long term.

Collaborate rather than compete

In the current market, you’ll find yourself meeting lots of other people starting their own journey into self-employment. But rather than worrying about the competition, think about how you might be able to collaborate.

There is enough work out there for us all to win.


Anna Sampson is a consultant

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Matthew Knight, Chief Freelance Officer, Freelancing Support, on 23 Aug 2024
“Thanks for sharing the link to our resources Anna, and your super helpful tips on approaching self-employment. It can be a challenging experience, but with a good support network, and knowing where to turn for support - it is also hugely rewarding. Next step - working with clients who hire freelancers to find more respectful and supportive ways to work with external collaborators!”

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