Empowering the Freelance Economy

Is the freelance life right for you?

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If you are on the fence about becoming or staying self-employed, then it’s time to explore your options. Gee Foottit of St. James’s Place Financial Adviser Academy shares a step-by-step Odyssey plan to help you decide


By Gee Foottit

Having the autonomy to decide what work you want to take on and defining your own hours is undoubtedly one of the main attractions of freelancing or contracting.

Perhaps you’re currently salaried and dream of making the change to self-employment. Or you’re already self-employed but facing unexpected hangups about the way your work and tax affairs have turned out.

Where employment offers the security of a reliable income, self-employment means that you get the flexibility to call your own shots – to a large extent anyway. But there are still downsides that you can find yourself facing.

“You can imagine a career and a life that don’t exist; you can build that future you, and as a result your life will change.”

Bill Burnett, creator of the Odyssey Plan

Whether you’re currently employed or self-employed, taking a moment to map out a clear plan that sets out your ambitious – but achievable – goals can provide you with the clarity and structure you need to take a step in the right direction.  This article will explain how an Odyssey Plan could help you to make changes that will truly work for you.

Weighing up the pros and cons of contracting

It can be a juggle to manage things financially as a freelancer when it comes to taxes and the loss of benefits that you would normally receive as an employee. As a freelancer, you may find yourself needing to secure your future pipeline of work through an umbrella company, such as an agency.

No plan completely survives first contact with reality, but being prepared allows us to remain flexible, engaged, and able to make thoughtful decisions on whatever life throws at us.

This regular stream of work can mean that you fall inside of IR35. In this case, you’re required to pay employment taxes and the same PAYE and National Insurance contributions as if you were employed, but without the same job security and benefits. This may suit you for now, but taking the time to weigh up all your options can help you decide what you want in the long term.

Perhaps you’re working solo and going contract to contract – this way of life can be exhilarating yet lonely and sometimes anxiety-inducing if you’re not always sure where your next contract is going to come from.

Is it time for a change or a plan B?

According to Statista, there are around 4.39 million self-employed workers in the UK and many more employed workers may be considering the shift to setting their own schedule and a greater choice of who they work with.

Of course, there will be many self-employed workers that feel they have the ideal set-up right now, but the nature of the beast is to always have a plan B.

No matter your situation, making any change can feel incredibly daunting. It can be difficult to weigh up the pros and cons in your head. Yet, the ability to easily transition to new work scenarios is a personal strength when it comes to being self-employed.

What is an Odyssey Plan?

An Odyssey is a ‘long and eventful or adventurous journey or experience’. Sometimes, the decision to make a change can be just that. Bill Burnett, Stanford Professor and author of Designing Your Work Life, created the Odyssey Plan to help people envision what they want their future to look like.

It’s not so much a rigid plan of action: moreover, it is a process of ideation that brings in all the underpinning values and belief systems from your work/life views, so it becomes a cohesive and multi-dimensional vision, rather than just a career trajectory.

No plan completely survives first contact with reality, but being prepared allows us to remain flexible, engaged, and able to make thoughtful decisions on whatever life throws at us.

Look at your current situation

Paint a picture of your current situation based on the things you know are happening in your current career.

  • What are you working on?
  • What does your day-to-day look like?
  • What hangups are you currently experiencing?
  • Is your career meeting your financial needs?
  • Do you feel a sense of passion or achievement in your day-to-day?
  • Can you see yourself sustaining your current career path all the way to retirement?

It’s important to do an audit of your career before making significant decisions. Once you feel comfortable with your current position, you may feel more ready to begin your Plan.

“Dysfunctional Belief: I should already know where I’m going. Reframe: You can’t know where you are going until you know where you are.”

Bill Burnett

How to visualise change

To build an Odyssey plan, you create three alternative realities on three sheets of paper. Each reality projects a five-year trajectory of both personal and professional milestones – at least one for each year.

To create your plan, build each timeline as follows:

  • Plan #1 – What would the next five years look like if you stay on your current career path?
  • Plan #2 – What would the next five years look like if Plan #1 disappeared?
  • Plan #3 – What would the next five years look like if money and image were no object?

For each plan, include the following:

  • A six-word title that captures the essence of the plan
  • Three questions to ask yourself – what would you like to learn from the five years?
  • A dashboard that indicates how you rank the plan against four criteria:
    • Resources: Do you have what you need to execute the plan?
    • I like it: Do you like the plan?
    • Confidence: Are you confident about executing the plan?
    • Coherence: Is the plan consistent with who you are?

Taking your plan forward

Once you have created three separate timelines, you can extend one of these into a 10-year plan. The 10-year plan can include elements from all three timelines but should still contain a dominant framework.

Reflecting on three different plans with three different scenarios and outcomes will help you to find clarity in what are looking to achieve. For example, whilst Plan #3 may seem unrealistic at face value, the elements that feature may remind you of what is really important.  

The 10-year plan follows the same structure as the five-year plan in that it should encompass both professional and personal milestones. It should also include three questions, and a dashboard to indicate your ranking of the plan.

As a life designer, you need to embrace two philosophies: 1. You choose better when you have lots of good ideas to choose from. 2. You never choose your first solution to any problem.

Bill Burnett

It should also include a thank you note. Imagine yourself at the end of your 10-year plan and write a letter to the person who designed it. Write about your plan as if it has already been completed, thanking the designer who created the plan for specific things that happened in those 10 years:

  • What will you be most thankful for?
  • How will you feel knowing that you’ve achieved what you set out to do 10 years prior?

This reflection is a valuable exercise because when you look back on the future, you can draw out the things that are most important to you.

A case study reveals why a career change can be positive

There are many upsides to making a change that better suits you, but a reassuring reminder is that making a career change needn’t mean turning away from the industry you love.

Emily Man, 50 from London, is rightly proud of her 20-year stint in film and TV production. Rather than change industry, she sideways stepped into a new field. Taking all that she has learnt about film, TV and advertising over the years, Emily has built her own business as a financial adviser and now supports those in the creative industry with their finances.

Although it was difficult, there wasn’t any point that I regretted it. I knew that the business would come if I worked hard enough, and I knew that I didn’t want to get back to production or to work for anybody else.

Emily Man, Financial Adviser

Emily comments, “In amongst running a production and coaching company, and everything that was involved including managing teams and finances, I was living contract to contract – it was high octane. But getting married and a desire to start a family eventually led me to look for something more stable.”

Emily trained as a financial adviser through the St. James’s Place Financial Adviser Academy and her business is going from strength to strength.

“Although it was difficult, there wasn’t any point that I regretted it. I knew that the business would come if I worked hard enough, and I knew that I didn’t want to get back to production or to work for anybody else,” says Man.

“I’m extremely thankful that I still get to work in an industry that I love, but rather than manage film projects, I’m doing something that I feel even more passionate about. I see the impact of the work that I do – even when clients are going through a divorce or caring for elderly parents, everything that I do has a positive effect on their lives. It’s incredibly life-affirming,” she says.

Embrace the question: ‘Where do you see yourself in five years?’

The question that is so often feared, may not be so bad anymore. Now you have the tool to break down your goals into manageable steps, you will be well-equipped to build a plan that feels far less daunting, and far more achievable.

Wherever you want to be, and however you wish to get there, the Odyssey plan will not only help you to visualise your future but also provide you with the framework with which to take the first step.

Good luck!

Gee Foottit of St. James’s Place Financial Adviser Academy

Download your free printable template Odyssey Plan here.

Interested in finding out if a career in financial advice could meet all of your goals and ambitions, why not watch this video to learn more?

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