I have a portfolio career. I have developed this career steadily over the course of more than a decade. Over this period my work has developed from side-hustles and freelancing into a proper career; one with purpose, direction, and development opportunities. This career allows me the flexibility and variety I crave. I get to work on the things I love, support my family and enjoy the lifestyle that I want.
Sound too good to be true?
Well, I will share how I have built this career and made it financially sustainable. But before we go on let’s look at what a portfolio career is and isn’t.
What is a portfolio career?
What does the term portfolio career mean and how does it differ from a side-hustle?
A portfolio career is either having several jobs at once or a number of jobs for a short time. The former definition is increasingly the most frequently used term and it is the meaning I will be referring to in this article.
I would also suggest that a portfolio career is not just a side-hustle or even multiple side-hustles. These things are similar, as there are multiple jobs involved, but a portfolio career is different to a side-hustle in the way strategy is different to tactics.
A side-hustle is generally a short-term tactic to improve cash flow or to start a new venture. These side-hustles can develop into a portfolio career, but they are usually a means to an end rather than the end itself. For example, you might do a part-time job to pay the bills while you are building a writing career or launching a start-up. Equally the writing or start-up might be the side-hustle that you do alongside your full-time job. The side-hustle, therefore, supports a transition or goal.
A portfolio career is less of a goal and more of a long-term career choice. It is a career strategy that builds multiple work opportunities and revenue streams into a coherent whole. This choice allows a particular lifestyle, career progression and set of opportunities. The jobs themselves may not appear related, but they are designed together, as I will demonstrate later.
Why would you want a portfolio career?
A portfolio career is not for everyone. It is not the only or best sort of career; it is just a choice. As with many decisions in life, it comes down to what you value most. The advantages and disadvantages of any career are generally linked to this balance and choice around these values.
People hold a variety of different values. These are almost always good things, but how we choose to prioritise those principles or beliefs defines our specific values. That prioritisation makes our choices differ from other people. For example, stability and flexibility are both great but it is hard to have both in your work. You often need to prioritise one over the other.
In the case of portfolio careers versus a traditional career path you might be weighing up these or similar values:
Traditional Career
Portfolio Career
Stability
Flexibility
Specialism
Variety
Security
Opportunity
Structure
Freedom
Table of career values (Simon Ash)
They are almost two sides to a coin; if you choose one advantage then you lose out on the other. The flip side of any choice becomes the disadvantage, the opportunity cost, of that decision. But we shall see later how to build a career to offset these downsides.
What sort of career is best for me?
Whether a more traditional or portfolio career is best for you really depends on what you value and what you are passionate about. There are no easy answers. A lot of the people I coach are trying to work out exactly these sorts of things and it takes time and reflection to really make the right decision.
It is important to remember that you can find your vocation, use your passion and stay true to your purpose in either type of career. For example, I have many friends who are doctors. They are passionate about what they do but, to follow that vocation, they need to specialise rather than multi-task in their career. No one would question that what they do does not have an incredible value, particularly in the present pandemic. The same could be said for a lot of other professions and vocations.
How do you build a portfolio career?
If you decide a portfolio career is right for you then to build one you need to maximise the things that align with your values and design the career to offset some of the potential risks and downsides of this sort of career. Therefore, you need to think about the role that each job or income plays in the overall career and financial picture.
To demonstrate this point I will use a farm analogy. One good thing about this analogy is that it shows that a portfolio career is nothing new. In fact, you could argue, developing a working life with multiple income streams has been around longer than the ‘work and then retire’ model. The farm, small-holding or cottage industry are all long-existing examples.
To keep things as simple as possible we are going to limit our model to four elements. That does not necessarily mean we have exactly four jobs or income streams, but we need to fulfil the purpose of each one.
For our portfolio career we will need:
The farmhouse
The cow
The chicken
The cash-crop
What should go in a portfolio career?
So, using this metaphor let us look at what should go in a portfolio career to support these elements. Each part of the portfolio has a career and financial purpose, as can be seen in the following table:
The Farmhouse
The Cow
The Chicken
The Cash-Crop
Purpose
Stability
Structure
Productivity
Passion
Income type
Fall back
Assured cash flow
Top-up cash
Windfall
Productivity
Slow
Steady
Intermittent
Volatile
Activity
Consolidate
Manage
Build
Experiment
Feels
Solid
Reliable
Useful
Inspirational
Table of portfolio career elements (Simon Ash)
We design the whole career working on how to maximise the things we value (for example the opportunity and flexibility) while managing and offsetting the potential downsides (like stability and security).
In this way it is like a financial portfolio, or a house build if you prefer these alternative analogies:
Farm Analogy
The Farmhouse
The Cow
The Chicken
The Cash-Crop
Financial Analogy
Asset/Pension
Bond/accumulation investment
Investment income/dividends
Speculative Investment
Property Analogy
Foundations
Structure
Fittings
Furnishings
Other career analogies (Simon Ash)
Managing the elements of a portfolio career
So, let’s look at how we develop and manage each of these facets in turn.
The Farmhouse
The farmhouse gives stability. The same goes for a traditional career but in a portfolio career, you need to be much more mindful of what your career fall-back is and how you underpin your long-term finances.
For me, this stability comes through property. I am not saying this is the right choice for everyone, just as an example of how I have built this financial foundation. My attraction for property is partly due to being an engineer by education and because I worked in the construction and housing industry. Therefore, I have always seen property not just as a home but as an investment opportunity.
I know that many people now are struggling to get onto the property ladder, and this may seem an unachievable dream but, by way of encouragement, I started off small and you might be able to do the same too.
My progression into property developed along these lines:
Pay off student debt
Save for a deposit
Buy the first property (that needed renovation) with my partner
Renovate property and create a second bedroom
Get a lodger
Start to rent out property whilst on holiday
Use a job opportunity to move out, rent out our first property
Save to buy a second property as we were renting
Let me point out the timeframe. It took me years to save up for a deposit and another ten years to go from one property to two. But we bought the first property knowing we needed income as soon as possible. The lesson? Start small but plan long with this sort of asset.
Using the gig-economy and developing passive income
When starting small you can join the gig economy. This allows you to start getting an income but also comes with some downsides. In our case, we had to compromise on our privacy when we got a lodger. We had to do a lot of work to advertise and prepare our flat to rent it out in the holiday season. The point is we started to leverage what we had.
What can you do? Maybe you can do something similar or rent out some storage space, workspace, a car-parking space? If you don’t have a property, what other asset could you leverage? You can rent out cars, household appliances and pretty much anything you can imagine in today’s gig economy.
Developing a passive income
In the world of Timothy Ferris, this ‘Farmhouse’ would be considered a passive income. It is a mature asset that brings a steady income or could be sold to raise capital. But anyone who has tried to get a passive income knows, developing a passive income is anything but passive! It generally requires time, money, and lots of hard work. If you want a business that gives you a passive income you first must build that business. If you want investments, online products, writing or property to be that financial base, you have to build them first.
So as mentioned before, start small but plan long. And start as soon as possible if you don’t have something already.
The good news is that once this part of the portfolio is built it is relatively low maintenance. The idea here is to consolidate the income stream and hold the asset for the long term.
The Cow
The farmhouse gives stability but may not bring much, or enough, in terms of cash flow. This is where the cow comes in. The cow brings a steady, reliable income.
For me, in work terms, this has been my career as a Reservist in the Military. This is a part-time job, one that provides a steady income, but it also gives me meaningful career progression and opportunities for personal development. I have been in the Reserves for more than 15 years and it is not something I could have done for that long if it was not something I enjoyed. It is not just a job to pay the bills (although it does help to do this), it is a career itself. As a leadership coach, being an Army Officer also keeps me honest and forces me to practice what I preach!
For you, it may be another sort of part-time role somewhere. It might be that you change your present full-time role to become a part-time one. This will take some negotiation with your employer, but I know plenty of people who have achieved just that.
The financial role of ‘the cow’ in the portfolio can be another investment or asset that provides a steady income. It is like having bonds or other investments that give you a steady return. Nothing dazzling, just reliable. If you are fortunate like me and can also make that something you value and enjoy, so much the better.
The Chicken
So now the baseline cash flow is assured. What next? Well, this is where the chicken comes in. The chicken gives top-up cash. It has some worth as an asset, but its real worth comes through its productivity. What it produces is also not enough to cover cash-flow needs on its own, but it boosts overall income considerably.
In financial terms, the chicken means that once we have paid the bills (hopefully these are covered by the Farmhouse and Cow), this is the extra we need for discretionary spending and luxuries.
This might court controversy but foreign holidays, designer clothes and eating at restaurants are all in this financial category. I am not saying you should not want or have these things (most of us do), but just remember where they are on the priority scale. In Maslow’s Hierarchy of Needs, these are similar to the basic physiological needs of food and clothing, but expensive coffee is more about self-actualisation than survival (although it doesn’t always feel that way in the morning!)
I say this as at times when building my portfolio career, I have had to do without some of these nice things in order to progress. Buying our first property completely cleaned us out of funds and for several years we had to watch every penny. But that budgeting allowed us to consolidate our finances and progress in our careers.
So, adding a chicken to the portfolio increases our income to more comfortable levels. Coaching, facilitating, and consulting is my ‘chicken’. It is a more intermittent cash flow, as it depends upon my business development and the time of year, but this creates an income that goes above my basic needs. The income is intermittent but generally very good when it does come in.
It is also not just a job that I am doing for cash. I love this work – particularly coaching leaders – and I find it deeply satisfying. But it is also very time consuming, so I must limit this work and, as a result, the income that comes with it. I need to do this to provide time for the final element of the portfolio career.
The Cash Crop
The cash crop is the part of the portfolio that is high risk and high reward. It is likely to be the thing you are most passionate about but won’t bring you an immediate income, or at least not enough of one that you can live off.
The cash crop gives the opportunity for creativity and experimentation and, if we are lucky, for a financial windfall. But there is also the chance we could fail at the loss of our time, and potentially some income, in the short term.
It might be that sometime in the future, the cash crop of today becomes the chicken, cow or even the farmhouse of your future career, but for today it is a new venture.
For me, my writing, public speaking and online business come into this category. I love creating and communicating content to a large audience.
As I seek to try out new things and nurture this part of my career it takes a disproportionate amount of time compared with the income it creates. So why do I keep doing it? Because it is my passion.
Also, the more this part of my portfolio career increases the more it supports the underlying reasons for seeking a portfolio career in the first place. It gives me a variety, challenge, and flexibility that I would not get otherwise.
So, what is it that you would dearly love to do? What do you do in your free time that you would also love to get paid for? These passions can be developed to become cash crops. You just need to think creatively.
For example, I love walking. No one is going to pay me to go walking right? And yet that is what I do. I coach people while I walk, I record my podcast while I walk, I make business calls while I walk. The fact is that you can take just about anything you enjoy, pivot the idea, and make it part of your work life.
When should you start your portfolio career?
The best time to start building a portfolio career is now. That doesn’t mean you have to quit your present job right away, maybe not at all, but you do need to start planning.
What sorts of jobs and opportunities do you think could make up the various aspects of your career and income? Using the analogy here, what would you list under each heading. They could well be blank. Don’t worry, they were for me at the beginning too! It also took some time for the various elements to settle into the structure.
The important bit is working out the next step. This should be something that you can achieve today. To help with the next step ask yourself: what is the best thing I can do today to take myself closer towards my dream?
Whatever your answer to this question is it probably requires an allocation of resources. How will you use your time and money? Maybe you need to set up a standing order from your bank to start building up some savings. Or perhaps you need to find a time every day you can commit to your passion. It could be that you need to hunt for that side-hustle or part-time job.
Whatever it is, put it in your diary now. (I nearly wrote dairy – the farm analogy has gone deep!) And once you have achieved that step, ask the same again: what is the best thing I do now to help me progress?
Will it work?
A portfolio career has worked for me. If it fits your values, you can make it work too.
I have been blessed to come through the pandemic in good shape and a lot of this I can put down to my career choices and how I built my portfolio together. I am not saying that it has been easy, but I can attest to the financial resilience of a portfolio career.
But as I said at the beginning, my career did not come together overnight. One of the greatest bits of career advice I ever had was from a former manager. They told me:
“Many people overestimate what they can achieve in a year and vastly underestimate what they can do in five or ten years.”
This wisdom helped me to plan and measure success over a different time frame. In the age of rapid fame and instant gratification, this is counter-cultural, but the advice has served me well.
And I think that is a great place for me to stop and for you to start. What is it you need to do today to develop your career?
Remember: start small, plan long, but start now.
Good luck on your adventure!
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If you want the right answers you have to start with the right questions
About The Right Questions
The Right Questions is for people who want greater clarity, purpose and success. There is a wealth of resources to boost your effectiveness in achieving goals, your leadership of yourself and others, and your decision-making.
Wherever you are on your journey, I hope that you find information on this site to help you on the next leg of your quest. Even if that is just the inspiration to take one small step in the right direction, then that is a success. If you can take pleasure in learning and travelling as you go, then so much the better.
I love to serve people, helping them unlock their potential, empowering them as leaders, and assisting them in achieving their goals. Please get in touch and let me know how I can support you!
In my last post I talked about the Stockdale paradox and coming to terms with the brutal facts of our situation. That is the first step in addressing our fears.
When one looks at the reality of where we are it can be scary at first but as you take think everything through logically it can start to dispel those fears. We need to ask ourselves, Ok, so what is the worst that can happen? If we analyse the problem in this way we can put things into perspective as often the worst thing is not that bad after all. We can also start to plan and work out how would we would act if the worst case scenario was to happen. In this way we can confront our fears.
Confronting fear
Confronting our fears helps us to avoid either living in a dream world or being crippled by limiting assumptions.
As the Japanese proverb says:
We need a clear vision and we need to understand the assumptions we have that either enable or limit our actions. Sometime negative assumptions are referred to as defeater beliefs but I think it is more helpful to think of them as assumptions as belief can have more fixed connotations and if negative, these thought patterns need to be challenged.
For example, when trying to introduce a change in your professional life you may face fears about your job, your promotion prospects or your financial security. This can trigger thoughts such as “I can’t do that – I would lose my job!” This is reasonable enough, as losing one’s job can have major consequences, but make sure you think it through. You may well find that:
If you are smart about how you do things then you probably don’t need to lose your job, or
That it would be worth the risk as you do not like your job anyway, or
You are pretty confident you could find a new and better job
There are plenty of other defeater beliefs that we could add in here such as:
“I won’t be able to pay my mortgage/student loan/credit card bill/monthly subscription to Sky Sport*”, or
“My boss/parents/family/imaginary friend won’t let me*”, or
“I will lose my friends/the good favour of my colleagues/the respect of my dog*”
(*delete as appropriate)
Overcoming fear
Whatever fears pop into your mind when you look at your present and future situation make sure you capture them and interrogate them fully. Assess each of them to see how real the perceived threat actually is. This way we can overcome fear.
We also need things in balance. Therefore when considering the ‘where’ question we keep one eye on the present and one on the future; one on the location, one on the vision. The dream of the future needs to be compelling enough to draw us forward, no matter what the challenges are that we face, and we will be looking at this aspect of ‘where’ in a future post.
Which fears have you faced and overcome? Which would you like to overcome?
If you want the right answers you have to start with the right questions
About The Right Questions
The Right Questions is for people who want greater clarity, purpose and success. There is a wealth of resources to boost your effectiveness in achieving goals, your leadership of yourself and others, and your decision-making.
Wherever you are on your journey, I hope that you find information on this site to help you on the next leg of your quest. Even if that is just the inspiration to take one small step in the right direction, then that is a success. If you can take pleasure in learning and travelling as you go, then so much the better.
I love to serve people, helping them unlock their potential, empowering them as leaders, and assisting them in achieving their goals. Please get in touch and let me know how I can support you!
The Seven Most Important Questions You Should Ask When Considering a Career Change
Work is a reality of life. The vast majority of people will spend a large portion of their life earning money in some job or another. The average person spends more than 90,000 hours at work in their lifetime (Psychology Today) so it makes sense that we should be doing something that gives us satisfaction as well as paying the bills. Getting the right job is therefore one of the big life goals and when we choose our profession or change our career we want to get it right.
“I think my job interview to be a bug sorter went well. I boxed all the right ticks.”
Where are you and what are you doing in your dreams?
So you are sitting at your desk, staring out the window; what are you dreaming about? Where do you picture yourself? Our daydreams can be a good indication of our yearnings, they can give insight into places we want to go and the people we want to be. What would you do if money and time were no object? What would you do if you had your time over again? Who would you most like to be like? What do you love doing, even if you are not being paid to do it? When have you had the greatest job satisfaction? Who would you most like to work with? Start making notes about what you want to do and this becomes a picture of where you want to end up, a personal vision statement. Then you can start to consider if you can make it a practical reality.
One very important thing to explore is your motivation for changing career. Why do you want a different job? Is there some compelling reason or are you just bored? Are you looking for something that aligns with your values or do you just think the grass is greener in another company or position? It is important to remember that there is an aspect of work that is always going to be just that, work, no matter how much you love what you do. No job or business is without its challenges and pitfalls so don’t expect a job change to magically transform all your problems, you may well find you take the problems with you.
As you start to refine your search to a specific job or company have a look and see whether your ideals and values are aligned with that business. Many people forget to do this and then wonder why they feel unhappy in their work, even when the job description seems to be just right for them. On balance, you are probably going to be happier in a place where people share the same values as you, than just somewhere with the right job title.
“If a man loves the labour of his trade, apart from any question of success or fame, the gods have called him.” Robert Louis Stevenson.
What is your dream job?
Once you have an idea of where you want to end up you can start to be more specific about the work, job, career or vocation you need to get you there. Look at the answers to the questions about your dreams and why you want to change careers and then put a job title or description to those notes. This is an important step in turning dreams into reality. You are defining success, giving yourself a definitive mission. Once you have something to aim for you are much more likely to hit the target.
Once you know the job you want then you start to need making a plan to get the job. You know where you are going, now take stock of where you are. Update your CV (curriculum vitae) or resume and see how suited it is to the job you want. Would you hire a person with your resume for the position you want? How could you tailor your CV to better suit the career you want? Are there gaps in your training, qualifications or experience that you could fill?
For information on the sorts of skills employers are looking for click here: Core competencies
Who do you know who can help?
It is a commonly used phrase that ‘it is not what you know but who you know’ that is important and this is frequently true in the job market. A large proportion of jobs – and arguably the best ones – are landed through networking rather than classified adds and job listings. Who do you know in the industry you want to work in? If you don’t know anyone directly then are there any friends or friends? Now is the time to use social media to your advantage. LinkedIn is particularly good for finding people and if you don’t know them directly you can join a group relevant to the industry you are pursuing and meet up with people there. Don’t ask people for a job; ask them for advice. No one is going to be offended if you ask them for advice. I have had plenty of coffees where I have either been giving or receiving information about certain jobs. These conversations may not lead directly to a job but they will help to answer questions and perhaps lead to other contacts.
Most of the time the best time to quit your job is when you have another one lined up. I always advise people not to jump ship until they have sorted out some further work. This is because it is very hard to follow your dreams if you are constantly worried about how to pay day to day bills. A good redundancy package can soften the landing but I know plenty of people who have still been scrabbling around for work as the money disappears. You may not have the choice, you may have unemployment thrust upon you. If that is the case then try to make the best use of your new found freedom to prepare for the job you want. Get an extra qualification or look at voluntary work placements that can help you further your experience (if paid ones are not available).
If you are looking for a specific position or opening you may have to wait anyway. The more specific the thing you want to do, the fewer the openings there are likely to be. Use your time to line yourself up as best you can but the wait will be more comfortable if you have an income.
If you want to read more about the importance of timing click here: When: Timing
Which way should you take to achieve your goal?
There are multiple paths you can choose from to get to your objective. It is worth thinking through the alternative ways that you could achieve a goal as significant as a career change. When changing career you may not be able to step directly into your dream job. There may be one or more intermediate jumps you need to go through, especially if you are changing the sector or industry you are working in. It is like using stepping stones to cross a river; there may be various options, and you may have to even make a sideways step at times, but you can still make progress towards your goal if you keep focussed on where you want to end up.
If you want to read more about exploring options and brainstorming different courses of actions click here: Which: Options
If you want further advice on career change I would recommend that you read “What colour is your parachute?” by Richard N. Bolles. You can click on title link above or the picture below to buy a copy from Amazon.
If you want the right answers you have to start with the right questions
About The Right Questions
The Right Questions is for people who want greater clarity, purpose and success. There is a wealth of resources to boost your effectiveness in achieving goals, your leadership of yourself and others, and your decision-making.
Wherever you are on your journey, I hope that you find information on this site to help you on the next leg of your quest. Even if that is just the inspiration to take one small step in the right direction, then that is a success. If you can take pleasure in learning and travelling as you go, then so much the better.
I love to serve people, helping them unlock their potential, empowering them as leaders, and assisting them in achieving their goals. Please get in touch and let me know how I can support you!