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The Portfolio Career Playbook ⎸ Nikita Khandwala
A playbook for portfolio-careering done right
Hiya! Portfolio-careers-done-well are notoriously shrouded in mystery. In today's essay, Nikita Khandwala lifts the veil on how she's built hers over the past 5 years.
By the end of this essay, you’ll learn:
the argument for building a portfolio career
how to craft your personal mission statement in under 20mins
examples of how to structure your work days & finances
tips on managing up
I welcome you to screenshot your fave bits & share them on LinkedIn (tag @generalistworld so I can say hi!)
As always, can’t wait to hear what you think.
Milly 👋
5 years. That’s how long I’ve been portfolio career-ing. But when someone asks me what I do, my stomach starts churning, my hands get clammy and my usual response is to turn to a friend and ask “hey, um, what do I do?”
post-dreaded-elevator-pitch
As well as becoming a black belt in deflecting, I’ve learned a thing or two through these painful conversations. One in particular, you might not expect: most people are building a portfolio career in one form or another. They’re just missing the language to describe how they spend their time.
Back in 2021, when I published The Portfolio Career Revolution, I shared a prediction made by the OECD that by 2030, 50% of professionals will be building a portfolio career. In that essay, I went on to discuss why I believed that individuals are the businesses of the future. Fast forward three years, a global pandemic and a heck of a lot of questionable AI startups later…let’s just say I have 10x more conviction in my prediction.
My favourite definition of a portfolio career came from Mallory Contois, who posted on LinkedIn that:
“A portfolio career looks like having multiple sets of experiences and skill sets at the same time, and diversifying your learning, knowledge, networks, and growth tracks. It broadens your surface area for 'getting lucky', or for stumbling upon exciting and interesting opportunities. It reminds you that the world is large, and there are many more ways than one to build a life for yourself.”
It’s particularly that last part that resonates with me: there are many more ways than one to build a life for yourself.
A combination of our ailing education system, inefficiencies in the labour market, and parenting defaults have conditioned us to believe that choosing a singular, linear path through which to ascend the mountain of life is the most secure and respectable way to live. In reality, this is simply a hangover from the specialist defaults encouraged by the Industrial Revolution.
In a world of ever-growing complexity, our individual needs and the needs of our society and economy are changing more rapidly than we could ever anticipate. Portfolio careers offer us a modern alternative that enables us to build a career that reflects that rapid rate of change. My favourite thing about portfolio careers (and the reason I will never shut up about them) is that they allow you to be “publicly multidimensional and human”, as Contois so eloquently puts it. To reduce our multifaceted humanity to a singular professional identity simply doesn’t do us justice.
The challenge, of course, is that if you’re taking it upon yourself to build your career in a way that’s different to what most people recognise as “normal”, you need to think about and manage your career differently.
💡 My advice is to think of your portfolio career as a company where you’re the CEO. Just like a company, you need to consider your product, your operations, your marketing, your financial and your cultural needs.
#1 Product: identify your portfolio career type
/In your portfolio career, you (and your unique combination of skills and experiences) are the product you’re selling.
There are 5 main types of portfolio careers that I’ve identified:
Spiky Generalists
Spiky Generalists hold multiple roles at the same time across different industries in either freelancer or fractional capacities.
Fractional Execs
Fractional Execs take on part-time leadership roles in multiple organisations, offering strategic expertise for a fraction of the cost.
Side Hustlers
Side Hustlers balance a stable job with entrepreneurial ventures or passion projects on the side.
Freelance Specialists
Freelance Specialists master one or two core skills and market those to different audiences, often working with multiple organisations at once.
Third-Act Advisors
Third-Act Advisors build a fairly traditional career before taking on multiple board, NED and advisor roles at the same time prior to retirement
Before you start your portfolio career, you should identify which type of portfolio career you want to pursue. Bear in mind that this doesn’t need to stay the same throughout your career. For example, I am currently a Spiky Generalist, but may become a Fractional Exec down the line.
Identifying your portfolio career type is important so you can build a structure that works for you, but becomes even more crucial when looking for roles, pitching your value, and negotiating flexible working patterns.
#2 Marketing: craft your mission statement
While shiny, newly funded startups may spend months refining their vision, mission and values before they’ve got their first MVP out, I recommend you spend a maximum of 20 minutes crafting your first mission statement.
You can agonise over this for weeks. Or, you can pitch → iterate → pitch → iterate. I’ve learnt that rather than leading my elevator pitch with a long-list of roles I hold, identifying the red thread that ties all my experiences together and expressing that as a succinct one-liner is the best way to help other people understand how I spend my time.
For example: I spend my time focusing on rebuilding education and economic infrastructure because I believe that interdisciplinary, generalist thinkers will play a critical role in tackling the most complex problems of our time.
💡 Here’s a template you can use, courtesy of Mallory Contois: I spend my time focusing on xxx because I believe that yyy (and I want to create zzz impact).
#3 Operations: design your operating system
In my experience, most startups think about operations way too late. Different companies have different operational loads, but the most important one to master first is how your company works internally.
One of the trickiest parts of building my portfolio career has been designing an operating system that works for me. What tech should I be using? How should I invoice clients? How do I integrate multiple calendars? Should I incorporate a company or remain self-employed? How do you manage knowledge and tasks across multiple organisations? Honestly, someone could make a business out of optimising systems operations for portfolio careerists (if you want to do this, hit me up, I’ll be your guinea pig!)
I would recommend investing the upfront effort to design a minimum-viable-operating-system that works for you.
Part of my Notion dashboard to keep track of my different projects
The key ones for me are:
A “doing work” and knowledge management platform: I highly recommend Notion. As a portfolio careerist, you get a lot of innovative and distinct ideas that emerge at the intersection of your different roles; cross-pollinating your ideas and insights across your work is paramount to moving the needle and Notion is the perfect platform to do this.
A simple project management platform: I also use Notion for this. Don’t overcook this. I’m definitely guilty of spending hours trying to perfect my task management system at the expense of actually getting the work done. Don’t be like me 😉.
An email client that allows you to context-switch easily: Superhuman. Try and get one of your clients/employers to pay for this as it’s quite expensive - the productivity gains speak for themselves so your pitch should be easy.
A reliable calendar and scheduling tool: Google Calendar & Calendly. I’ve started using Notion Calendar recently and so far I’m loving it, because it seamlessly integrates my to-dos in my schedule. They also have their own scheduling links so you don’t have to pay for another scheduling platform. The only con of Notion Calendar so far is that they don’t yet have an Outlook integration, but if you don’t use Outlook, you’re golden!
A communication platform that enables cross-company comms: Slack (I should honestly be a Slack ambassador at this point). Slack Connect enables you to set up channels with people outside of your organisation, which means you can centralise all comms across clients in one place. While this may not always be possible, depending on the comms infrastructure of your client/employer, do your best to stick to Slack.
An effortless design tool: Canva. You can develop your own brand palette, visualise your ideas, effortlessly whip up new brand assets whenever you need them. A no-brainer.
When you’ve got your minimum viable tech stack set up, you also want to think about how you structure your days and your weeks. Work with your rhythms and productivity ebbs and flows.
I start every day with a 2-hour writing block as that’s when I do my best thinking, so I try not to book any meetings before 10am.
I do my need-to-do but “non-thinky” work just after lunch when I’m having a slight productivity slump.
I also have a dedicated 30 minute “recalibration” block at the end of the day, where I tie up loose ends, do some urgent comms and then plan the following day.
One of my teammates splits her week into “creative” and “management” days. Creative days are spent doing whatever she feels called to do on that day, whereas I want/feel called to do and then Management are meetings, calls and to-do’s. Experiment for a couple of weeks and figure out what works for you.
#4 People: master managing up
The biggest difference between building a company and building a portfolio career is that, as a portfolio careerist, you are most likely a team of one. That means you need to have a generalist skillset, while also leveraging your clients, bosses and collaborators as effectively as possible.
Now that you’ve got your infrastructure set up, you need to figure out how to get the most out of yourself and the people you collaborate with. Because I’ve built my portfolio career in the fast-paced startup world, I realised pretty early on that over-communicating and managing up were two of the most critical levers for success.
My number one tip for managing up is this: put yourself in your boss’ shoes. Your boss likely has 5-10 reports and is fielding fires all day every day. If you come prepped with a clearly articulated problem, a data-backed point of view and a proposed solution, you’re going to make their life 10x easier and find it way easier to get stuff done. Couple this with constant over-communication (even more necessary when you work flexibly or you work in a remote/hybrid org), and you’re on your way to making needle-moving impact.
#5 Culture: create containers for reflection
Much like Peter Drucker’s oft-cited adage: “Culture eats strategy for breakfast”, when it comes to your portfolio career, culture will eat YOU for breakfast if you don’t give it ample time. While the culture in a startup refers to the invisible rules that bind your team together, the culture in your portfolio career is about how you choose to develop yourself as a person and a professional.
As a portfolio careerist, you’re usually responsible for your own development and upskilling. For most people, this constantly sits in the important but never urgent quadrant of your Einsenhower’s Matrix, but with the half-life of skills getting shorter every year, setting aside time in your week to actively learn and reflect outside of your day-to-day is a game-changer.
For the past 1.5 years, I’ve been doing monthly peer coaching and will soon start working with a professional coach. I’ve also got dedicated blocks on my calendar for weekly reflections and daily “recalibration”. Even if you don’t stick to these every single week (I certainly don’t 😅), creating intentional containers for reflection is key to consistently delivering quality outcomes for your clients/employers while maintaining your sanity!
The other thing that is a common cultural challenge for portfolio careerists is knowing when to set boundaries and how to prioritise different opportunities. Since most portfolio careerists are proactive generalists, we often also fall into the DIY Trap (s/o to Shern for this great framing!). Sure you can do everything yourself, but should you? This is why having clarity on your mission statement is of the utmost importance.
Whenever a new opportunity arises, I assess it through the lens of my overall mission and ask myself: Will saying “yes” to this opportunity move the needle on my mission in a way current opportunities can’t? If the answer to that question is positive, I then think about the opportunity cost of the opportunity and whether my answer should be “yes, today!” or “yes, someday!”
If you were building a product as a CEO, you would try and get that product to revenue/profit as quickly as possible, before exploring new business lines or products. Do the same for your portfolio career.
One of the most compelling reasons to start a portfolio career is that you can diversify your income streams and increase your financial security by no longer relying on a sole employer. However, this comes with its own challenges.
The most important thing to remember when consider your finances as a portfolio careerist is to walk before you run. Focus on building up one consistent income stream that you can rely on to cover your baseline costs, before layering further income streams on top of that.
Conclusion
Building a portfolio career can be one of the most liberating and empowering ways to build a life you love, but pursuing this route requires grit, adaptability and drive. The more you can approach building your portfolio career like a business, the more you maximise your chances of success. If this essay has got you curious about building a portfolio career, continue bingeing on some of our favourite resources below…
Wanna keep bingeing?
On Product:
On Marketing:
On Operations:
On People:
On Culture:
Nikita KhandwalaNikita is a proud portfolio careerist who spends her time rebuilding education and economic infrastructure to unlock the potential of interdisciplinary thinkers and doers. She’s part of the Generalist World team and is Head of Partnerships at the London Interdisciplinary School. |
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