Portfolio Careers for Lawyers – An Essential Guide

portfolio careers guide

What is a portfolio career, and why might it be a great solution for jaded lawyers thinking about a career transition?

There’s no doubt the world of work has changed for almost everyone since the global COVID-19 pandemic.

Not being tied to the daily commute to the office, working from home, and using technology to get things done that previously could “only be done face-to-face” has opened a lot of eyes to different ways of working.

Changes such as these may have also crystallised your feelings of dissatisfaction with your legal career and a growing realisation that the law isn’t fulfilling you professionally or personally.

In the past, the decision you had to make was whether to leave the law completely or dig in and stay the course.

With the hurdles in the way of leaving often seeming high, the decision to stay in your current career seemed to be the obvious one – until sometime down the line when your health or mental well-being deteriorates to a point where there really isn’t a choice.

But for lawyers who are looking to improve their career satisfaction in a different way, or who are looking for a more gentle transition out of the law, choosing to develop a portfolio career can be a great choice.

What is a Portfolio Career?

At its most basic, it’s simply having more than one income stream.

But beyond that, a portfolio career can be as complex or varied as you wish.

What attracts people to the concept is that it can be a mix of any full-time or part-time employment, freelancing, starting your own business, consulting, or taking on one or more non-executive director roles.

These can all happen at once, or be spread over time.

Key ingredients are the variety and the new and different challenges it can bring, as well as potentially giving you more control of your work and working practices.

This might seem quite a radical approach for lawyers but, in truth, it’s something that some have always done.

I’ve known solicitors who did paid DJ sets at the weekend, a barrister who bought and sold antiques as a paying hobby, and countless other examples of what are now referred to as “side hustles” or “gigs”.

Building a portfolio career is just a way of formalising other areas of work into additional income streams that can enable you to “do less law”.

Types of Portfolio Careers for Lawyers

Lawyers choose to structure their portfolio careers in lots of different ways.

Usually, the two headline choices are to stay working as a lawyer alongside one or more other things or do a mix of non-legal work.

What’s right for you will depend on your attitude to risk, and may change over time.

Think of these options as “starters for 10” rather than fixed paths you must walk down.

Law as the Primary Career with Secondary Gig(s)

For lawyers who are most risk-averse, it may be that legal work is still your primary work.

You may stay in your current job and start something on the side.

Your other chosen income streams are (for now at least) secondary.

This option prioritises stability and allows you to continue using your skills, contacts, and qualifications as before.

Choosing this portfolio career option could be as simple as adding an “after-hours” income stream to the mix, or it could involve going part-time in your current role to make time for something else.

It’s a great way to start a transition process away from the law without having to take a huge leap of faith.

Other lawyers may be less risk-averse and leave their current role and work as a lawyer in a different capacity alongside something else.

For example, setting up as a self-employed consultant, taking on ad hoc work on a freelance basis, or working on shorter, fixed-term contracts for only part of the year.

The ‘Seasonal’ Portfolio

If you have an interest outside the law or a side hustle that’s seasonal, you can structure your portfolio to do that when you can, and law becomes the “gap filler”.

Or some choose to do this as they like variety and the legal work interests them and/or contributes a good portion of their annual earnings.

Lawyers who find great success working in this way tend to have organised their life and finances to a point where they have a “whole year” plan and don’t need to rely on a steady income month in, month out.

People with experience in self-employment or freelancing tend to be more comfortable with this ‘annualised’ approach to life.

The Non-Law Portfolio

For those who know the law isn’t for them anymore, a portfolio career can be a great alternative.

Either as a stepping stone option as they explore other potential career options or as a career option by itself.

Perhaps a mix of well-paid work for three days a week and lower-paid, but more meaningful, work for the other two days a week.

Is a portfolio career right for you?

There’s definitely a certain “type” of person who is most commonly attracted to a portfolio career.

Barbara Sher, the bestselling author of ‘Refuse to Choose’, calls them scanners.

One of the most fundamental characteristics of a scanner is a curiosity about numerous unrelated subjects—they are interested in pretty much everything!

If this sounds like you, then you may be particularly suited to a portfolio career.

So for people who like variety, who struggle to choose one thing to devote themselves to, or for those with a love of travel or time-consuming hobbies, a portfolio career is likely to be a rewarding choice.

It can also be a very good way to keep one foot in the law while using the other to step into other areas and see what works for you.

In other words, it can be an ideal transition choice before you leave the law completely.

My own portfolio career

I thought it might be beneficial to outline my own story of transitioning out of law and into work I absolutely love.

I built a portfolio career through necessity rather than choice, but now I wouldn’t change it for the world!

I had enjoyed an outwardly ‘successful’ legal career, culminating in a senior role with Sky Sports in the UK. But I knew that it wasn’t giving me the fulfilment I saw my friends enjoy in other careers and lifestyles.

To cut a long story (involving two years of soul-searching, procrastination, doubt, fear, and research) short, I made the decision to leave the UK and head for Australia.

After a bit of time off, I needed to get myself an income, but I also needed time to start exploring new career possibilities.

I landed a four-day week part-time maternity cover role at an Australian TV company, leveraging my experience from the UK.

This gave me one day a week to learn about and plan for the property business that I really wanted to set up. In these early days, I even bought and sold things on eBay to boost my savings.

Later, while running my property business and starting a coaching business, I took a directorship in an e-commerce company.

This was a great fit because, not only did it bring in some income, I was able to learn skills that would directly impact the success of my other businesses – how to market a business on the internet!

Fast forward to today, another part of my current portfolio is executive coaching for MBA students and for sports professionals/sports industry executives.

This is a great crossover for me because I love sports and have good experience working on the legal and business side of top-level sports and media.

I can draw on this when I’m coaching my sports and business clients to help them get to where they want to be.

And, whilst I no longer run a property business day-to-day, it did leave me with some investment properties which form part of my income portfolio.

Other Examples of Lawyers’ Portfolio Careers

There are many other lawyers who have embraced the portfolio career. For example:

  • A former corporate lawyer who set up a ski holiday business for the winter seasons, and is a consultant lawyer for the rest of the year.
  • A lawyer who moved to freelance lawyering to allow him to DJ part-time in Ibiza.
  • A lawyer who swapped employment for short-term contract work, allowing her to start and run a novelty cake-making business between contracts.
  • An experienced media lawyer who transitioned freelance legal work, taking on work for 9 months of the year and then travelling for the remainder.

Not for everyone

Let’s be realistic, a portfolio career is not going to suit everyone.

First of all, it can be bloody hard work, particularly at the start.

It can add stress to your life at first, rather than reduce it, and there may be an element of reduced financial security.

If the thought of juggling more than one job makes you wince, then building a portfolio career is probably not going to suit you.

Similarly, if you enjoy “deep diving” into a subject or really becoming an expert in your field, you’re not going to be able to achieve that as well by spreading yourself thinly across more than one role.

On the other hand, if you wish you had more control over your career path and your earning potential then portfolio careers can give you what you are looking for.

If set up correctly, a portfolio career can let you regulate the flow out of the “money tap” to suit your needs.

It can also help you have the ultimate flexibility and allow you to ‘design’ your work and life exactly as you want it.

Where to start?

So, assuming it’s a good fit for your character and your goals and ambitions, how do you start to transition from being a lawyer to having a portfolio career?

The great news is this is something you can test out in a small way initially, and then develop as you go.

The process is often one of evolution, not revolution, and the experiences and contacts you pick up along the way will help to guide you towards building the perfect portfolio career for you.

Here are some ideas for starting your own portfolio career:

Try an out-of-hours gig on the side

For some lawyers, this is the ideal first step.

You can start a business or take on a new contract which you can work on while keeping your primary career unchanged for now.

If you commute using public transport, this could be the perfect time to work on your side gig, for example. Others choose to set aside an hour or two each evening, or in the morning if you’re an early-riser.

Obviously, I don’t need to tell you that you should check the terms of your employment contract before you embark on anything like this!

Change your working practice

Another option is to reduce or condense the hours you work at the moment to release time for another project.

This doesn’t just have to mean asking to work part-time.

Other flexible working options are now available.

You could increase the number of working-from-home days you do (releasing commuting time for something else). You could also negotiate a condensed working week.

By working longer hours Monday to Thursday, for example, you get a week’s work done in 4 days, allowing you to devote a full day to your new project.

Take the leap

Some people feel ready to take the leap, quit their current job, take on a new part-time role and then devote solid hours to new career options.

Having faith that it will all work out for you can really help with this (and it usually does just fine!).

If you have already built up a financial cushion in anticipation of change, then this can be a really motivational thing to do, but for others, it could be a step too far, too fast.

What to avoid

There are so many pitfalls to be wary of – I should know, I hit most of them myself!

But there are a few specific traits common to lawyers that could be blockers to your success.

The first is that you need to let go of any innate concern for detail and getting everything right.

I cannot begin to count the number of hours I (and many others before me and since) wasted on minutiae like logo design, choosing a font, colour schemes, building a website, or agonising over the perfect business name when setting up a new business.

In the beginning, simply run with the minimum viable product to get yourself off the ground.

Make some money first, then decide if it’s worth investing in all the good stuff I listed above.

That way, you’ll only spend your time developing ideas that actually work.

If you’re looking at multiple employment and/or freelance contracts then feeling like you need to know this is 100% ‘right’ for you can be a big blocker.

Yes, you should absolutely do some due diligence and not leap recklessly but, at some point, you would be better served by making a change, trying something new and seeing how it goes (in reality, rather than in theory).

You can always course-correct again later if you need to.

The other thing people get hung up on is that you must come up with a business idea or something that generates income.

That’s not true at all.

Remember, a primary reason for building a portfolio career is for your own satisfaction and well-being.

You could volunteer in a field that you’re interested in, or take a low-hours role with a charity or other third-sector organisation.

These offer huge potential for networking, learning about alternative career options, and helping you to build ideas that could develop into income streams later on.

Lastly, don’t expect a linear progression.

Portfolio career paths are much more meandering than a traditional route through a legal career.

For many, that’s one of the big attractions, but if you’re not prepared for it it can be disconcerting.

Think of your portfolio career journey like that of a sailing yacht.

You know the destination, but the exact route to it will change with the winds and the tides.

These early forays into a portfolio career will give you invaluable information, build whole new networks, and allow you to begin to adapt and change, with more variety and freedom.

So, what’s next?

If all this is resonating with you, what are the next steps you should take?

The first thing is to do what I like to call “field research”.

Step away from the internet and seek out real people who’ve done what you’re looking to do.

Speak to them about their journey, what worked, what didn’t, and how they felt about it.

Then consider your own personality, motivations, strengths and weaknesses.

Make sure that you can cope with the potential downsides of building a portfolio career.

These include less security, the potential loss of career “identity”, juggling multiple demands on your time, a possible reduction in holiday time to begin with, and the increased energy you’ll need to succeed.

All that said, you’ll probably surprise yourself with how resourceful you are should you try out the portfolio career path.

I would certainly recommend it as a potential option to explore – myself and many other former lawyers love it!

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Matt Oliver

Matt is the founder of Law Career Plus and a former in-house lawyer (Sky Sports, London & Foxtel, Sydney). With over 12 years of experience as a career consultant & executive coach, he supports lawyers with their career development & career transitions. He does this through this website, a regular email newsletter and his one to one lawyer career coaching.

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