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What are the challenges of working for yourself?

If you have ever wondered what it would be like to ditch the PAYE (I mean how many people actually work 9-5 these days?), then here’s the skinny.

This post is about the hard parts of running your own business. Tomorrow I’ll post about the good bits (spoiler: I think it’s totally worth it).

If you are considering starting up on your own, or already work for yourself, or even if you are just curious, this post will give you some honest insights into what it’s really like. (although my experiences will not be exactly the same as others’).

Small business challenges

I never thought that running a small business would be so challenging. I started Trevnee right before the pandemic hit which definitely made it trickier, but it has still taken me by surprise.

I freelanced for a total of six years, so I thought that I knew what it would be like to have my own company. For me freelance was always straightforward. I was never short of work, and it built year on year. Below I’ll talk you through the benefits of freelancing and what’s harder about a small biz. But I’ll also explain why freelance didn’t work for me.

The ups and downs of freelancing

I freelanced twice. The first time I did it for just over a year and I was fully booked the whole time. The second time it took me three months to get established. After that I consistently overbooked (more on this later), and my contracts (and the value of my contracts) increased every year. It was more than ten years ago, and I often did the fabled £10k month. In fact, I once did a £32k month. So, if that’s a measure of success then I was a successful freelancer.

The pluses of freelance as opposed to PAYE:

I tend to think that these are pretty obvious, but I’ll give a quick rundown. Most people that go freelance know why they want to leave their regular job despite the security and continuity that offers.

freelance, small business

  • The freedom to choose who you work with and when

  • Not being tied to an office (although I had a lot of longer jobs where I would work a day or two a week on client sites)

  • Generally the pay is much better (but you have to take into account that this covers holidays, sick-pay, insurances, pensions, parental leave, administration time, credit control, job insecurity, time to prepare pitches and apply for new work etc.)

  • You usually move on before the politics of an organisation starts bugging you (not always though)

What I found with freelance in reality is that I simply transplanted my unhealthy working habits: taking on too much, never being able to fully relax, trying to please everyone all the time and worrying excessively if I couldn’t, over-delivering on promises and expectations, and having my laptop open at all times of the day – so a poor separation between work and home.

I think before I freelanced I imagined that I would travel more with my husband when he was away for work, just do contracts that I wanted and enjoyed, and would work from coffee-shops (Ah, the old totally over-rated coffee-shop work fantasy). It wasn't really like that, and you have to be very disciplined if you want to maintain balance. I also missed my old boss who was a lovely supportive person that had my back when I was stressed with clients and was a great cheerleader; and my team who were brilliant at bouncing ideas around, picking up the slack (and filling in my skills gaps), and making work fun. Freelance could be lonely despite my lovely network because the buck always stopped with me, and the everyday social support wasn’t always there.

That said there were definitely pluses to freelance as opposed to starting a small biz. And they were these:

  • quickly got established

  • enjoyed the pitching process and found a lot of success with it,

  • was part of a large professional network of other freelancers and businesses (the Not Office Christmas dinners were pretty fun)

  • socialised a lot with prospective and existing employers and fellow freelancers (that’s good networking IMO) so there were lots of fun meet ups

  • one company I worked for employed loads of contractors and they put on regular events and CPD days for us, which was great

freelance, small business, working from coffee shops

Ultimately though, the bad outweighed the good. I still didn’t have the freedom and autonomy that I really value. Working from a coffee shop is pointless if what you want is to establish the culture and values that you work within. It's just window dressing. And I was working within an industry that wasn’t right for me. So while freelance wasn’t my jam, that doesn’t mean it’s a bad option.

Freelance v small business, solopreneur

The hardest parts of running my own biz

I thought that the business skills that I have from working in a business and from freelancing would translate to running a small business. But I have found that I have had to learn a lot of new skills and to be resilient in different ways.

The biggest difference is that establishing a business takes a lot longer than establishing yourself as a freelancer.

My reason for setting myself up this way, as opposed to pitching for contracts, is so that I get to work with my ideal clients and I get to establish the culture and ground rules about how I work.

I genuinely enjoy going to work every day. And if I choose to do extra hours it’s because I want to. Yesterday, for example, was really busy and I worked from 10 until after midnight. But if I need to take a day off next week, I can make decisions like that at the last minute.

Solopreneur, small business challenges

Here’s what challenges me most in solopreneur life

I think I was quite naïve when I started. I didn’t know how difficult it would be to get eyes on my website. I hadn’t realised either how time consuming, or how frustrating social media marketing is. Not being able to meet people face to face in the real world because of the pandemic meant that my non-existent online selling skills was very problematic, since the whole business is online. I actually thought that getting clients would happen quickly (but it’s a very slow process to establish a consistent client base).

Because of this becoming profitable is also a very slow process. And from what I understand, this is the case for most people. New businesses tend to take between 1-3 years to fully establish, and if you are starting from scratch it’s closer to the three year mark.

The nice thing about that is that I love working with clients so much and at this stage can give them extra care and attention because my time isn’t overly stretched. I’ve learned that this is something I definitely want to continue in the future: so I know that I want to prioritise quality of experience and value over volume. To date most of my clients have come from networking, and from clients to whom I’ve offered free sessions becoming paying customers later on. But, this isn’t a sustainable model, so I am also continuously improving my marketing and communication skills.

Practical things to think about before starting a new biz

small business challenges, freelance

  • Do you have the money to sustain you through the lean early months?

  • Are you aware of your skills deficits and blind spots, and how will you prioritise which to invest (time, effort and money) in first?

  • Are you able to outsource any tasks that are beyond your skillset? (this will speed up the process but it’s all a time/money balancing act.)

  • Do you have the social and emotional support to help you when you are wailing and crying about whether you will ever see the results of your hard work? (just me? Haha!)

  • How well do you cope with being alone a lot of the time? (do you need colleagues/ a strong network?)

  • Do you have the shit tonne of resilience, good humour and optimism you need to keep going?

In case you are put off, tomorrow I will tell you about the fun and exciting parts of working for yourself. Please get in touch to tell me your worries about changes you are going to make to your work patterns in the future, or that you are currently in the middle of? I’d love to know. You can either e-mail or DM me on my Instagram.



I'm Jodie Lamb and I have been running Trevnee Coaching since early 2020. I've been an accredited life coach since 2008. I focus on Careers and Change. I work with people that are either thinking about changing things in their work and want a plan and support with acting on the plan; and people that are experiencing any kind of change in their lives and need help to make the most of it.

I write a weekly newsletter. I promise to only send you useful tips, strategies and occasional offers and never to spam you! I'd love it if you'd sign up.


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