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As soon as you start to be intentional about shaping your 2nd Half Career, you will be faced with important choices.  These are the top 10 ‘gotchas’ that I have seen amongst professionals as they begin to move forward.

1 – Expensive Postgraduate Qualifications

The first pitfall to avoid in setting up your second half career is to assume that the best thing to do is to invest in a very expensive University accredited programme like an MBA or other Masters, a postgraduate diploma or a PhD.  If you are making a radical change from being an accountant to being a psychotherapist then, yes, you are going to invest in a massive amount of expensive education. But very often you can move to your 2nd Half Career by using transferable skills and tactical training courses and learning as you go, rather than investing in a very expensive accredited programme. It is not just the cost; it is the time commitment required.  Remember, at the end of the process, you still have to find a job.

2 – Assuming that just doing the same thing, but as a consultant, is completely straightforward.

You have decided step out from being an employee to being self-employed and believe that this is a completely forward shift. But you probably underestimate: the support system you had while in employment, the amount of effort required to go out and find work, the amount of resilience you require to persist in the bad times as well as the good times. It will not just business as usual to move from being an employee to being self-employed.

3 – Over investing in unnecessary stuff at the beginning

You are a ripe target for a whole industry of service providers looking to exploit you at start-up.  You will be tempted engage expensive accountants, website development, business cards, graphic design and business planning consultants.  You risk doing all of this stuff too early, in your 2nd Half Career. All of these things can be valuable investments.  But do them later, when you have really worked out what you are doing, and when you are starting to bring some income in.

4 – Waiting until you are completely ready before you go out and find work.

There are all of those things that you might think need to be in place before you can find work.  I would urge you to just go out and start to find work immediately and the best time to find work is shortly after you have ended your salaried position.   It is when you are freshest, the most energetic and the most enthusiastic. It is when you have the richest and most current set of relationships and your current employer could be the source of your initial contract. So, go out and start finding work straight away rather than waiting until you have everything ready.

5 – Telling yourself you need a break

Maybe, you have been made redundant or you have resigned from a demanding role.   You ‘need’ or ‘deserve’ a break of all your hard work.  Perhaps you want to take a year off to work out what you really need to do.   You may have the financial resources to have no income for a year, to spend more money than you normal for a year.  You may also have enough money in the bank at the end of that year to invest in getting started in your 2nd Half Career.  You are exceptionally lucky.  Most of us do not have that luxury.   I would strongly encourage you to move from your current employment to getting started in your new career immediately if you know what you want to do. Even if you do not know what to do, get started in something.  Once you get started in something you’ll start to understand what you do want to do. You are used to working, carry on working!  Work your way into a new future.

6 – Underestimate the amount of networking needed

You are very likely to underestimate the amount of networking you need to do.  You may be unskilled in networking, have prejudices against networking and inexperienced in using networks as a powerful support system.  Again, and again I find myself recommending that you should go out and talk to people and ask for their advice. You are not necessarily asking for their work or for their contacts but most people are flattered to be asked for their advice.  Even people that are not very strong connections of yours, where you don’t feel that you have long standing friendships are often open to being asked for advice.  Just saying ‘can we have a coffee?” is not necessarily the most powerful way of having an interaction.  If you are purposeful and intentional, they will know why you are meeting and what it’s for. You will have a much more powerful conversation. So, I would be saying “I’m setting out on my 2nd Half Career and I’d really like to have some advice. Can we meet up and have a conversation and so I can get some advice?”  It could just be half an hour over coffee, or it could be over lunch, or a drink after work or at a seminar: but asking for advice is often a very easy way of renewing and developing your network.

7 – Being overly optimistic about how quickly it will all develop

Yes, you may get your first contract or your first assignment very, very quickly and that is fantastic. You may even have one in the bag before you leave your employment.  But building up regular work will take time and you have to be ready to face rejection again and again. You really have to be prepared to have lots of people say ‘no’ so that a few people can say ‘yes’.  If you talk to sales people and you have an honest off the record conversation with them, they will be clear that most of their conversations are with people who say ‘no’ and that is part of the process. You need to accept that every person who says ‘no’ is taking you one step closer to the person who will say ‘yes’.

8 – Undervaluing what you have to offer

This is not just about pricing. This is really about explaining to other people the benefits, the value, of what you are going to bring.  You need to turn that value into something that is meaningful for them.   In a business context that is all about how they can make money (more income), save money (reduce cost) or better manage risk.  You need to restate your activity to explain the impact.  This is your value proposition.  It is not what you do that matters, you may do great things.  It is the impact that you have on their business that counts.  You are an expert on what you do.  They do not necessarily care about how you do it.  They are more interested in what effect, what benefit, it will have for them.   So again and again you risk undervaluing, failing to demonstrate the value of what you do whatever your professional background.  Reframe what you do to say where it makes a difference, how it makes an impact, to the people you are serving.

9 – Not properly looking at how much you have to charge to make a decent income

Your numbers may be different but don’t fall into this trap: “In my current employment I am getting £120,000 a year, so £10,000 a month and then there is some tax taken out of that and so on.   I get 6 weeks holiday and work 46 weeks a year.  I take £120,000 divide by 46 weeks and 5 days per week: and I should charge about £500 per day.”  But you have forgotten all the other elements involved in work.  You may have some sick days. Hopefully not very many, but you need to factor them in. Now just 45 weeks of work. You need to spend time attracting and finding clients.  You will need to spend time learning new stuff.  You need time to operate your business (doing the accounts, billing clients, building a website, etc).  A more realistic approach is to plan on twelve fee earning days per month and four days building and developing your business.  This will help to make it sustainable. Now allow one day a week when you can do some thinking, go to a conference or course, and keep up to date with what is going on in your specialism. If you are earning £1,000 a day, twelve days a month, ten months a year then that is £120,000.   If you are earning £500 a day then your income is just £60,000. You need to wake up to the difference; setting your rate target to meet your income needs.

10 – Failing to account for lost benefits of employment

As well as recognising the day rate you need, you also need to take account of the fact that when you were an employee you were getting pension contributions from your employer, national insurance contributions from your employer, paid holiday, maybe medical insurance, access to a company car, free training and conference attendance, sick pay, maternity pay and redundancy pay. The employer paid expenses and allowances.  You may also have benefited from access to IT systems and on-line resources.  In your new world this all needs to be costed in.


Being intentional to build the right 2nd Half Career, particularly if you are going to move away from full-time salaried employment, can bring you a whole new lease of life.

Avoiding these common pitfalls, will smooth the path and increase your chances of finding the freedom and joy of a workstyle that serves you for decades to come.


Charles McLachlan is the founder of FuturePerfect and on a mission to transform the future of work and business. The Portfolio Executive programme is a new initiative to help executives build a sustainable and impactful second-half-career. Creating an alternative future takes imagination, design, organisation and many other thinking skills. Charles is happy to lend them to you.