Why Permanent Jobs Are Overrated

Many people can’t understand why I chose not to have a permanent job.

When I started working fixed term contracts, I was surrounded by Australians contracting on working holiday visas. It didn’t feel like a crazy thing to do.

When I resigned from my permanent job, my friends and family where shocked. Years later, some of them still can’t understand it.

“When are you going to settle down?”, “When are you going to buy a property?”, “When are you going to get a career?”. “Why would you want to work somewhere for a few months and risk being unemployed at the end of it?”

Here are the reasons why, and why I recommend contracting.

1. You have more control over your career

Getting off the gravy train I had to make my own way. It was up to me to find work that I found interesting, that I wanted to do. Staying in one role at one company is rarely going to take you in that direction. Sure, you can change jobs after a few years, but do you really want to spend the time in between doing work you don’t enjoy?

Shortly after I was given my first permanent contract, the work I was asked to do changed dramatically because of the downturn in the economy.  I was asked to change departments.  I didn’t mind, but it wasn’t what I wanted to do. It wasn’t what I had signed up for.  I could either stay on the road that my career was unexpectedly taking, or I could leave.

Since leaving, I’ve had some great roles, and learnt a lot more than I would have done if I would have stayed where I was.

Of course, I’m still tied to doing whatever work I’m given. But if that work doesn’t sit well with me, at least I’m free to leave within a few weeks if I want to.  (This did happen. I was asked to do some legal work connected with the creation of missiles and tanks. I hated the fact that I was working on something that could destroy human lives, and was glad that the end of my contract was in site.)

2. It forces you to produce better work

A lot of permanent employees I’ve met coast.  They’ve fallen into a rut, they’re unhappy in their jobs, they stress out and shy away from doing anything different or challenging, and generally spend their time trying to do as little as possible. I hated working in those environments. You’re the average of the five people you spend the most time with. Spending all day with people like that can destroy you.

As a contractor, you’re under pressure to perform. You need good references to get your next job, or to get your contract extended.  Your skills need to be sharp, and given the breadth of knowledge you need in order to find more jobs, you can’t get complacent.  I liked the challenge. It forces you to prioritise learning in a way that is not expected of you in many permanent positions.

It’s when you’re pushing yourself, that you’re growing. If you’re in the same position for a long time, it’s easy to get comfortable. You do the same work day in and day out.

The worst that could happen wasn’t crashing and burning, it was accepting terminal boredom as a tolerable status quo. Remember – boredom is the enemy, not some abstract “failure”” – Tim Ferriss

In reality, opportunities for permanent employees to challenge their skills with new or interesting work are few and far between. In-house, the best work is often farmed out to private practice lawyers. If the work stays in-house, those assignments are hotly contested, and usually given to those who have been there the longest.  To grow, you have two choices – stay in one role long enough to hopefully be given those assignments, or challenge yourself by moving elsewhere and learning a different role.

Too many people choose to stay in the same role for years purely because it’s the easy option. I have friends who hate their jobs but don’t want to move as they want to spend the majority of their time in the office planning their wedding or buying a new house.  They don’t feel that they could take advantage of a new employer in the same way that they can with their current employer so they choose to stay where they are.

3. You get more variety 

For many people, twenty years of experience, is really one year of experience repeated twenty times” – Andy Hargadon

Working in a variety of roles gave a much wider experience than I would ever have got, had I stayed in one role.  Secondments are becoming more frequent, but are not always possible and are rarely in your control.

Having a breadth of experience will help you see things that others don’t.  Unless you’ve been exposed to issues on other deals or matters connected, that are not directly related to the work you’re doing, it will be impossible for you to connect the dots. I’ve worked on deals where there have been Bribery Act and money laundering implications which were all missed. Not because the lawyer wasn’t good at her job, her narrow experience just meant that she had no exposure to those issues.

In a world where the market is constantly changing, we need to be able to adapt.  I’m in a better position now that I have a broader experience than if I had stayed in one role for 10 years.

4. You meet more people

“Opportunities do not float like clouds in the sky, they are attached to people” – The Start Up of You

Working for different companies and people will give you a far wider network than your average permanent employee.

Every job you will ever be given, will be given to you by a person. It’s people that decide who will get the job, when jobs will be advertised, what resources will be allocated to fill a role, and who will get to know about it.

My network has been a key factor in increasing my chances of getting work. Industries are incestuous. People move around and people talk. If you have an old colleague that can vouch for you at an organisation you want to join, that’s valuable.

Being able to get on with people is one of the most important skills in business. I’ve worked with enough muppets and unpleasant people in my time to know how important this is. I’m not the best lawyer in the world but have a decent reputation for getting on with people. It’s one of the reasons I’m hired.

By moving around, you increase your chances of being able to work with great people. People who impress you, and who you can learn from. If you’re not working with those people, move. Don’t get stuck working in a dead beat team for years, your skills and motivation will quickly deteriorate.

You’re the average of the five people you hang around most. Your environment will shape your income, your skills, your outlook, everything. Working with people who are sloppy at their jobs won’t do you any favours.  As a contractor, whenever I’ve found myself in that situation, I’ve tried to get out of it ASAP, even if that’s meant potentially leaving a contract early, (which I’ve been fortunate to avoid – it doesn’t help your reputation as a contractor if you break your commitments).

5. It makes you different

In a world where millions of people could do the same job as I do for much cheaper, being different pays.

I’m not for everyone. Some employers look at me and don’t understand why I haven’t had a permanent position for so long. They prefer people who have worked in one narrow field for years at a time.

In the eyes of others, my experience stands out.

6. It’s not as risky as it’s made out to be

Nowadays, jobs are rarely for life. All companies are under pressure to reduce their bottom line and every few years redundancies are used to get rid of the dead wood and boost the profit margin.

Staying in one position for a long time can be riskier than contracting.  Laid off permanent employees are often more at risk than unemployed contractors. Permanent employees rarely have a good network of people they can turn to for help.  They’re not used to looking for new opportunities, interviewing or marketing themselves. They’ve become complacent, with worn out soft skills and a narrow knowledge base which will make it difficult for them to pivot to something slightly different if they have to. They also find the redundancy process and exit traumatic.

Risk is a part of life. Pursuing any opportunity is a risk. It might work out, it might not.  Risk is not the same as uncertainty. There is always going to be a lot of unknowns no matter what we do. It’s easy to overestimate the risks involved, (my grandmother for example, was convinced that we are all going to die of ebola. Yet statistically, we are far more likely to die of a myriad other causes) and scare yourself into doing nothing.

Career wise, every move is a risk. You might join a new company and hate it, the work might be too difficult, and the people may be terrible.

If you can tolerate the worse case scenario however, then pursuing an opportunity and taking a risk often makes sense.  When considering job changes, death, homelessness or permanent unemployment are rarely real possibilities.  The worst case scenarios are probably going to be disliking your new work/colleagues/commute, or find yourself being made redundant soon after you’ve joined.

You cannot predict the future, disasters are rare, but do happen. Resilience is the key. By taking small risks regularly now, we will be in a better position to weather the bigger ones, the Black Swans of life.

“Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty…The resilient resists shocks and stays the same; the antifragile gets better.” ― Nassim Nicholas Taleb, Antifragile: Things that Gain from Disorder

7. It allows you to experiment

Contracting allows you to work for different companies, different industries. You get to experience different ways of working. Some will be better than what you’re used to, some will be worse. Both are valuable.

If you are considering a permanent role with a company, a temporary stint to begin with is the best way to find out if you’re a good fit for the company, and vice versa.

Sure, you can leave a permanent position if you find that you don’t like it after you’ve joined, but notice periods are often long, and the stigma attached with leaving a permanent position after less than a few years will not make it easier for you to get another job.


There are downsides of course, and as I’ve got older they’ve begun to bother me a lot more.

1. Lack of meaning and fulfilment

I found contracting interesting and useful for when my main goal was to save and have the flexibility to travel. Since I’ve hung up my rucksack, contracting is pretty unfulfilling. Assignments are relatively short and you can rarely have a real impact or pursue meaningful work. You know that you won’t necessarily be working there in 10 years time and won’t have the opportunity to work on bigger, longer term, projects.

You don’t have the same sense of growth and progress that you get in many permanent roles.  If you want to “progress” your career in the conventional sense – managing a team, getting those job titles with big salaries, then contracting is probably not the way to go.

2. Financial instability

In some industries, like IT or medicine, contractors earn a lot more than they would do if they did the same job as a permanent employee.  In other industries, like law, you usually get a similar salary to what you would get if you were on a permanent contract, often minus the benefits.

It’s much harder to get a mortgage as a contractor.  You often have to show that your current contract has been extended at least once, and submit bank account statements showing a steady stream of income for the last few years. You need to save for periods when you might be unemployed, and you rarely get the same set of benefits as a permanent employee – maternity cover, pension, sick pay, healthcare, company discounts etc.

In an economic down turn, contractors are usually the first to go. You are at risk of being out of work and need to be able to deal with that.

3. Unwanted quiet periods

For me, travel was hugely important and I took extended break between contracts.   If you’re in a relationship however, it can be difficult for your partner to have the same amount of time off, or be off at the same time.  Even if you’re both contracting, the chances of you both getting a contract that starts and ends at the same time are slim.  Roles rarely come up when you want them to, which means you risk unemployment for a while at least.

4. Competition for the best assignments

Interesting work is often reserved for permanent employees.

It can be hard to get work too. There’s often a stigma attached to being a contractor. Old school workers don’t understand why anyone would choose a different path to themselves. They assume that contractors are only on the market as they’re too useless to get a permanent job. They’re skeptical, and don’t see the value in working for shorter periods for different companies.

I’ve also met plenty of low quality contractors who give contractors a bad name.  These are the people who have usually been laid off and ideally want a permanent position but settle on a temporary role to tie them over.


For me, playing the time game, fighting for promotions and pay rises in law firms or in-house, might make sense if you managed to get on the property ladder in the nineties or early noughties when property was affordable. You might be able to make enough as a partner or a senior in-house professional to live in a family home in London, and send your kids to a school where they won’t be stabbed. Now, things are different. Mortgages, rent, student debt, transport costs, and school fees are the highest they’ve ever been. You’re going to need a lot more than the average lawyer salary to keep your family afloat.

I’m not sure how I’m going to deal with these issues in my own life yet. In the meantime I’m doing my best to be in a good position to work and make the most of my life at the same time. For me, the best way of doing that for a long time was contracting. Now my priorities have changed, it’s no longer my first choice in life.

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