How to Enjoy (and Succeed) Going Self-employed

(from Alan Heeks book Out of the Woods: Staying happy when you’re over 64!)

Whether you’re jumping into self-employment or being pushed by outside forces, it’s a fact that the percentage of men who are self-employed, and not on someone’s payroll, grows strongly through the 40s, 50s and 60s.  I was 42 when I left my well-salaried job, handed back the company Jaguar, and sat at home alone in my dining room with the answerphone.  I have enjoyed the freedom of being self-employed, but there are downsides, especially the risk of isolation.

I know many men who are literally one-man bands: it’s hard to sustain your morale and motivation over a long period with no colleagues and work mates, especially if your business hits problems.  Whilst the term self-employed may suggest working solo, there are ways to work with others on this basis.  For example, you could be a sub-contractor to a small team or a large organisation.  You won’t get such benefits as paid holidays or pensions, but you have the freedom to walk away when it suits you.  This kind of set up not only gives you some social contact in your work, but can also mean that you don’t have to learn skills you don’t want to, such as selling your services, or IT.  After six months of working on my own, I realised that I needed to work with people, and that the kind of training and consulting work I wanted to do needed a large team with a bigger range of skills than I could offer.  I became an Associate Consultant of a management consultancy based near me, which meant that I could work as part of their team, but was free to do my own independent work in parallel.

If you are considering going self-employed, or have already made the jump, here are some pointers to help you enjoy it:

Plan before you jump: It’s far less stressful if you can build up your contacts, skills and finances while you’re on someone’s payroll than when you’re out on your own and have to pay the bills every month.  If you know the direction you want to go, you can probably do some of this legitimately as part of your current job, or else do some in your spare time.

–Lower your breakeven: This is explored in more detail in the Money GOLDMINE article.  Do whatever you can at this stage to cut your monthly outgoings, and so reduce the minimum income you need to earn when you are self-employed.

–Look for baseload income:  This means trying to find a steady source of income, probably part-time, which hopefully covers your breakeven expenses, and means that you don’t need to worry if your self-employed freelance earnings build up slowly.  One friend of mine trained as a psychotherapist in his 40s, and when he left his paid work in market research, he got a long-term contract to work two days a week as a student counsellor with a university.  Jobs like this are out there, and you might find such part-time work on an employed basis.

–Figure out the sales and marketing: If your type of self-employed work needs a steady stream of new clients and contacts, you’ll probably find that one third of your time is taken up in prospecting – making new contacts, writing proposals, promoting yourself via social media, having exploratory meetings.  You need to understand this aspect of self-employment, and either embrace it gladly, or consider alternatives.  Becoming a sub-contractor to a bigger organisation who does all this is one good option.  Sometimes you can find individuals or agencies who do this for you, and you pay them for each new client they generate.

–Have some savings before you start: Being self-employed is pretty insecure.  You can’t control the flow of customers, let alone recessions and credit crunches.  Try to start with a financial cushion: not only for the early period, but also to help you out if you hit a lean patch later.

–Know and meet your social needs: Maybe you have a great social life quite separate from work, but for many men, work is a major source of social contacts.  Be clear what you need, and how you can meet this when you are self-employed.  There may be local networking groups you can join, or try to find congenial people who you can set up with as a partnership or small team.  Managing these working relationships can sometimes be difficult and demanding, but a team should have more capacity, more skills, and more resilience than any one-man band.

A cunning plan: Whatever your line of work, it’s going to be crucial to have a business plan.  Finance is just one vital part of this: it also needs to include sales and marketing, skills training, any certifications you need, and lots more.  Ask one or two competent friends to be a sounding board for your plan.  And if this stuff is not your forte, there are good books on these topics.  Even the banks offer some useful briefing for small business start-ups, or you could look for a helpful accountant – there are some out there!

Remember your vision:  You may know the saying, “when you are up to your neck in alligators, it’s hard to remember that you came here to drain the swamp”.  Hopefully, you have a vision which excites you about going self-employed.  Try to keep in touch with that spark of inspiration.  It may help to have a review every six or twelve months: one friend of mine doing tough, pioneering work in holistic health care had an annual half day review with me and another professional to help him review his progress towards the vision, and make sure he did not lose himself in the daily details.

Wise Advice about Self-Employment

If you try a Google search, you will get millions of listings in this area.  Here are a few which may help you get started.

PRIME Business Club is the Prince’s Initiative for Mature Enterprise, specifically aimed at helping those over fifty into self-employment.  You can access some good briefing material through the Prime Business Club, but also potentially make some networking contacts and even find a mentor to help you get started. this is a useful website for a range of situations, created by Citizen’s Advice.  If you search on self-employment, there is a useful short checklist of practical issues, with links to further information. At the time of writing, the UK Government still offers help for small businesses, including the self-employed, and you can access some of this through this website.

Going Self-Employed: How to start out in business on your own – and succeed! By Steve Gibson.  ISBN 978-0-7160-2188-9.  This is a useful, readable manual which covers most of the practicalities, including such issues as sales and marketing.




Be your own boss: Teach yourself by Matt Avery.  ISBN 978-1444111842.  This is another good, practical guide, covering some of the human issues like self-confidence as well as the logistical ones.