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Earlier in my career I was an IT contractor, working as a software developer, introduced by agencies.  Projects typically ran from three to six and sometimes as long as nine months.  I understand the opportunity that being a contractor can be for people.  It can appear to be more rewarding than permanent salaried employment.  However, I believe there are 10 reasons why, in the longer term, being a contractor won’t Make your Future Work.

1.  The challenge of continuing to build relevant skills in your marketplace

This is particularly intense for people in the IT area where successive waves of technology can very quickly make those premium skills that you honed earlier in your career, irrelevant.  But I think it applies in many other cases, whether it’s marketing, sales, finance, operations, HR or project management.  The whole subject area continues to evolve.  What’s fashionable and important is constantly changing.  As you get older, it becomes harder and harder to continually update your skills while maintaining contracting activity.

2.  It’s very difficult as a contractor to evolve your career

As a contractor you are hired as specialist who gets things done. You often won’t be given the kinds of opportunities you need to manage and lead.  You are limited to delivering your specialist skills.  Again, referring to my experiences in the IT area, you can start perhaps, to have a team leader role, but project manager roles are more difficult to take on.  If you are pigeonholed as a software developer this undermines your ability to increase your rates.  As you get older and older you are likely to become irrelevant.

3.  HMRC rules have changed

The whole set of rules around being self-employed or trading through a limited company have changed.  The traditional model for an independent contractor, was to work through an introducing agency, who then sold your time by the day.  Then you are paid for every hour that you’re contracted to work.  However, the increasing implementation of IR35 in all larger employers, means that the time for money contract is likely to be seen by HMRC and by employers, as a hidden employment relationship.  

You can get around some of these challenges by writing statements of work and taking financial responsibility.  However, this becomes increasingly difficult because employers just don’t want to take the risks and agencies don’t want to take risks.  You end up working as an employee of an umbrella company and more of your gross value is taken out through taxes and charges by the brokers in the system.  In the past, it was very attractive when you could take dividends out of a company and charge a good premium on your salaried rate.  Now it almost becomes a loss making proposition compared to a salaried employee who is getting pension, holiday pay and sickness bundled into their annual salary.

4.  You become subject to ageism

Over time, you become subject to the same ageism that is pervasive in so many areas of employment.  Although surveys have demonstrated that employers see older workers as more productive and more reliable.  This hasn’t changed the attitude of recruitment managers or the agencies that serve them.  Again and again, I talk to contractors who’ve got stuck in a loop where they are seen as overqualified, which is often code for you’re just too old.

5. You thought being a contractor was working for yourself but it feels like being employed

In a sense, as a contractor, you are working for yourself because you are freelancer  But actually, you have very little control over how you do your job and how you build your future.  It’s all mediated through an agency and your contract client.  To truly work for yourself, you need to be able to pick your hours, choose your clients, define your proposition and not rely upon expensive intermediaries who ultimately control your every move.

6. There isn’t the option for working part time

It’s very difficult to move from a full-time contracting relationship to a part time contracting relationship so you can build other opportunities into your life.  Occasionally, I’ve seen contractors who can negotiate a three or four day a week relationship, but most roles are seen as full time.  As you move to the 2nd half of your career you may want the time to pursue a side hustle or to have more flexibility in your workstyle because you’re supporting elderly relatives or challenging teenagers.  Full-time only can become a real barrier to Making your Future Work.

7.  Remote working may not be viable long term

As you get older, you may be less inclined to buy into the 3,4,5 workstyle that so many of the contractors that I’ve met must commit to.  I have had spells when I spent three nights away from home, four days on the client site and the fifth day working at home.  It makes it impossible to participate in a normal family night or a conventional social life or build commitment to regular community activities [choir, sports club etc].  

Although during COVID remote working became the norm, I fully anticipate the demand to be onsite and be present in person will increase.  As you get older you potentially have to look further afield for the assignments that are available then 3,4,5 or even 5,5,5 (having to travel to the client on Sunday to be ready for Monday morning) working becomes inevitable. 

8.  It’s very difficult to do anything else

It’s very difficult to start a business while you’re an independent contractor.  In fact, any substantial transition is hard.  This is because as a contractor you often build the contracting workstyle into your whole financial planning.  This means that you’ve built financial commitments that rely upon being able to work 240 days a year at the rates you’ve been able to command.  When you’re not working as a contractor you’re not earning.

Taking a sabbatical is a very expensive experience.  Even reducing the number of working days can become very expensive.  As people get older, the gaps between assignments can get longer.  The pressures on working harder while you’ve got an assignment increase and your capacity to develop any other alternatives like a business become vanishingly small.

I’m reminded of a good friend who I knew for many years, who I would meet every two or three years.  He wanted to talk to me about starting a business.  But as a highly paid contractor, he recognised that the commitment made to school fees, university fees, mortgage, etc.  meant he had to carry on working at the same rate.  So now, in his early to mid 50s, he is in a place where contracting is the only thing he knows and the only thing he can do.  Whereas I made the decision much, much earlier in my career to break out of the contracting treadmill.

9.  You’re not enjoying the corporate environment

To a certain extent, as a contractor you are shielded from the internal politics.  You are one step removed from the day-to-day political wrangling.  Everybody knows you’re not going to be there indefinitely.  

People want you to succeed but, inevitably, you’re coming in from outside and you will challenge the status quo.  That will mean that you are subjected to corporate politics.  Many people I talk to have got to the point where they don’t really care about the corporate politics anymore.  They’re tired of fighting them.  

10. You want to believe you are making a real difference

Time and again, as you get older your life develops, you are keen to move from whatever success you have achieved earlier in your working life, to care more about the difference you can make.  This shift of focus from success to significance is very difficult to achieve within a contractor workstyle.  As a contractor you are just a ‘gun for hire’ and will usually have very little involvement that will enable you to influence the organisations that are you clients.  Typically your relationship will be short-term and tactical.  


In summary, I see lots of individuals who step out of full-time salaried employment and see the contractor work style as a viable alternative.

It can certainly be attractive in the short term, promising more flexibility more variety and more opportunity.  But in the longer term I would suggest that it’s a fix that fails.

There is another way… check out to find out more.


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.