4 min read
07 Aug


“Should I stay, or should I go?” 

Remember the words to that Clash classic: 

"If I go, there will be trouble             

And if I stay it will be double" 

The most important thing to remember is that the only way to eliminate job problems is not to have one. Which is, for most of us, unrealistic. 

Leaving employment to go it alone means that you will exchange one group of challenges for different ones. But if you accept this, it may be your best move ever. 

This is not meant to be a how-to guide. Here are my top picks for proper books that are written by other people who are doing it very successfully: 

What I’ve done here is write a few thoughts based on my experiences. For context I worked for eighteen years in corporate marketing analytics roles. As a business owner I still operate in the same area. 

That made sense for me because I love the nuts and bolts of what I was trained academically and professionally to do. I can command decent fees and so work fewer hours enabling me to add voluntary roles to my career. 

Of course, the beauty of starting a business is that you do not have to stay in the same field you were employed in. Some start off selling what they know, retrain, and gradually pivot their business towards more of what they really want to do. 

I have written under several headings where I think that the employed and freelance experiences are probably the most different: 


This is not something that employees need to consider that carefully to begin with. I only really became properly aware of exactly how the teams I worked for generated revenue and profit when I had director roles and responsibility for part of the P&L.

If you run a business, you need to think about whether you will sell products or services. Will you sell lower value stuff to many, or higher value to a few? How much do you need to sell to cover business costs, pay the bills, boost your pension?

Products probably take more time to research, develop and launch but are more scalable freeing up your time when the money starts coming in. It is not a route that I have taken yet because my job satisfaction comes from doing hands-on analysis.

I sell high value services to a handful of clients a year. I prefer working with just one or two clients at a time, although sometimes that is difficult to achieve in practice. Where data is concerned delays in delivery often mess up careful scheduling!

The biggest difference to employment, even though I produce similar work from a technical perspective, is that I am in full control of who I work with and how. I decline prospects that are not a good fit and have terminated a client contract too.     


You really do need to be comfortable in thinking about and talking about money as a business owner. If you do not adopt the right mindset then your business venture could easily become nothing more than an expensive hobby. 

A risk when offering services is to give away consultancy for free to clinch a sale. But every hour that you spend courting, convincing, chatting with a prospect before you engage is a cost to your business that you need to recover to operate profitably. 

A fee is not a salary. It must be high enough to: pay your business expenses (insurance, software, professional services), cover periods when you are not working (holidays, sickness, childcare), pay you enough to cover your personal expenses. 

In my experience you may also need to be prepared to negotiate on fees (or scope) and follow up on late payments. Thankfully, I have never been involved in legal action over payment or contractual disputes, but it does happen. 


Unless you are employed in a marketing role this is not an area you will know much about when you set up a business. I am a marketing effectiveness analyst and yet I was clueless about how to get going when I first started. 

With or without a marketing budget you will need to spend some time thinking about how you will bring in new customers and wave to existing ones. I worked my corporate network to begin with, but people move on so this will not work forever. 

If you are also ambivalent about selling you need a strategy that attracts the right potential clients to get in touch. Be clear about what you are selling and who to. Be present where they are and let what it will be like to work with you shine through. 

Consistency works best for me. If I lose inspiration for what to write about, I draw on something that has happened outside of my business. More personal material can get surprisingly high traction if it is clearly authentic and showcases your personality. 

I am an analyst by trade so naturally review how effectiveness my marketing is, test alternatives and tweak accordingly. Just remember to stick at one strategy for long enough before changing it up. Unpaid strategies are a long game. 

Mental health

This one varies enormously between individuals. For me, my mental health radically improved when I left employment. I became less happy as I had more senior corporate roles because I was removed from the hands-on work that I love to do. 

I also made the transition later in my career when I had a comfortable financial cushion to fall back on relatively low regular outgoings. The lumpy income takes a bit of getting used to – not for the faint-hearted or undisciplined. 

I am an introvert and adapted well to the relative isolation of working for long periods alone. There are plenty of supportive communities both online and offline who can replace colleagues until you build a team of your own if that is a goal. 

Natural tendencies do not change much though. Running a business can be all-consuming so take care if you are prone to overwork. I do sometimes need reminding of the bigger picture and that I have earned enough for the year. 

Making it

I found that most if the companies I worked for when employed all had similar and a narrow definition of success. More revenue was good. Famous clients were good. There was an expectation of progression from doer to manager to leader. 

I was not happy as a leader despite the handsome compensation. Now I have created a business where I can do more of the analysis that I love. I work with different types of clients now too, so I am learning more new things. 

It was not possible for me to commit to significant voluntary work while I was employed but I can now run my client work around these other commitments. I am now on the road towards becoming a trustee which is another life ambition. 

It is getting quite difficult to keep my business as small and simple as I want it to be. But I know that I could easily end up hiring a team and getting back into a similar situation that I was in before I quit employment. 

The thing is, it is literally my business and nobody else’s. I set the goals which can be as conservative or stretchy as I like. And be flexed to accommodate changes elsewhere in my life at a speed that is difficult to achieve employment. 

Wrapping it up

If you leave employment and start a business understanding that you are letting yourself in for a different set of challenges rather than solving all your employment problems, you will do fine. If you are not sure, start it as a side hustle until you are. 

There are some aspects to business that I think are different from employment: model, money, marketing, mental health and making it. If you would like a chat, get in touch. I would like to pay forward the help others gave me when I started out. 

Please ask before reproducing my material partially or wholly for commercial use.
© Jo Gordon Consulting Ltd 2021

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