5 Tips for Transitioning from Full-Time Employee to Freelancer (or Consultant, Entrepreneur…)

I never thought I’d start my own business, or even work freelance; it wasn’t really on my radar as a possibility. After school you went to university, after university you got a job – a full-time job, with an employer and a monthly salary. When I first quit my job three years ago without a concrete plan as to what I would do next, I slipped quickly back into the idea of getting another position, going to interviews for some really interesting roles in different industries. At one point, however, I just said: that’s it, I’m giving it a go, I’m setting up my own company.

Starting up on your own comes with a whole host of challenges, which are completely unfamiliar after many years in full-time employment. Some of these are linked to the running of the business itself: even if you’re a staff of one, you need to manage your cash flow much more carefully than when you had a steady salary flowing into your account, and you have all the admin of sending invoices, doing your taxes, and so on. Other challenges are more to do with the day-to-day working environment: having the discipline to manage your time and energy effectively, choosing which projects to work on, and knowing when to take a break.

I’ve found that I’ve enjoyed learning all the new aspects that come with running a business, while I tend to be very self-motivated and good at working independently, so the whole thing suits me quite perfectly (my Myers Briggs profile tells me that I would “do best to establish myself as an entrepreneur or a consultant”).

Here are my 5 tips to you as you’re quitting your full-time job and transitioning into a role as a freelancer, consultant or business owner:

1. Get really clear on your WHY

There’s a lot of talk these days about finding your purpose, whether it’s a question of a business being purpose driven or it’s you as an individual knowing what motivates you in life.

When you quit your job, and you make a big career and lifestyle change, people are going to challenge you. They’ll ask you why you would do such a thing, they’ll raise concerns based on their own fears of leaving what feels comfortable and familiar, and you’ll be asked to justify your choices. More than that, you’re bound to have your own doubts – after all, you are taking a risk and the future is by no means guaranteed.

As you face challenges and doubts from yourself and from other people, knowing why you’re doing what you’re doing will help to give you the confidence and conviction that you’re doing the ‘right thing’. Not only that, having a clear purpose will motivate and energise you to achieve something that is meaningful to you. Without a boss, you won’t have any one to tell you what to do so you need to be incredibly self-motivated and driven without that external pressure; and knowing your ‘why’ will be a huge enabler.

2. Work out the money thing

I’ve written about this many times before: money is not the biggest driver for most of us, we have many other values that we deem to be more important in our career and in our lives more generally – HOWEVER, money remains a big consideration for all of us. As a result, it’s best to confront this issue head on.

Addressing your concerns about money in a tangible way will help you to feel more comfortable about making the changes that you are making and, again, drown out that voice (inside or out) that questions whether or not you will be successful. This means doing some calculations as to your basic living costs and making plans to cut down on these as much as you can; working out how long you can live on your savings and when you need to start bringing in an income; and how much of an income you need.

Again, it’s easy to start having doubts as you continue on the rollercoaster of freelance and entrepreneurial work, with the inevitable highs and lows that come with this kind of business. Knowing that you have a plan, a concrete figure of how much money you need and a specific deadline for when you need it, can help you to stick to your guns and keep moving forwards. It will also give you a clear indication for when you need to recognise the reality that your current business is not going to be viable and you’ll need to consider other options.

3. Create the structures that work for you

One of the biggest attractions of the freelance lifestyle is the freedom it brings. Freedom to choose your own clients, to work when and where you want to, and to be your own boss. However, that very freedom that we so long for is also a potential curse!

You’re often completely alone, working from home or from a café, and you can feel quite isolated at times. As I’ve already mentioned, you need to be incredibly self-motivated and disciplined in order to manage your time effectively without the structure that you’re used to. This applies to your work projects, of course, but also to other areas of your life: making time to cook healthy food and to exercise, putting your work aside to spend time with friends and family, and giving yourself permission to take a break. It’s important to be prepared for this and to create a system that works for you.

I went through an initial phase of rebelling against any kind of structure at all, refusing to set an alarm in the morning or plan any rigid agenda for my day. These days, while it’s still hard to establish a routine given my irregular schedule and my travels, I’m striving for more of a balance between maintaining my freedom and flexibility on the one hand and having some form of structure and stability on the other. If you think you need more structure to your day, check out my article over on 99 Designs on How to design an ideal week.

4. Find your tribe

One structure that I do 100% believe in is a support network. Working freelance or setting up a company on your own can be a lonely business, but there are thousands out there going through the same thing and finding these people will reassure you that you’re not alone.

You need people who believe in you, who will encourage you and love you unconditionally. You may be lucky enough to find this kind of support in your family or your existing friendship network; if not, if your immediate network struggles to understand the changes you’re making, then you’ll need to look elsewhere.

The first time I realised that I wasn’t alone was going along to an evening talk at Escape the City in London: every single person I spoke to that night was going through the same thought process and the same career transition process as I was. Since then, I’ve found The Yes Tribe, an adventurous group that just bubbles with enthusiasm whether it’s about wild camping under the stars or supporting an exciting new business idea. Find your tribe, and you’ll be much more likely to succeed in your endeavours.

5. Keep learning

As you leave behind your full-time job, you’re coming from a world with which you were very familiar, where you knew the rules and how to operate within them, and diving into a whole new world. It’s hardly surprising that you won’t know everything right away in this new environment, so adjust your expectations and get ready to learn.

Learn about accounting and taxes, about building a website and promoting yourself on social media; learn about networking, about pitching new clients and closing the deal; learn about managing your own time and energy, and setting the boundaries so that your work doesn’t overtake your personal life. Learn about your personal style and preferences as to how you work, the clients you want to work with, the type of projects you most enjoy.

Learn by reading the latest books in your area and on other topics, finding the leading blogs and influencers to follow, talking to people, getting out of your comfort zone.

Learn by reading the latest books in your area and on other topics, finding the leading blogs and influencers to follow, talking to people, getting out of your comfort zone.

Never, ever, get complacent; never stop learning!

Leaving a full-time job behind to work independently is an exciting process, and one that can also be quite scary. Following these 5 steps, I think, will help to make your transition more enjoyable and, ultimately, more likely to be a success.

Good luck!


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