Let's start by clarifying what we mean by a portfolio career by breaking the subject into three parts:
- The objectives of a portfolio career
- The typical routine for someone pursuing a portfolio career
- Unique risks and opportunities of a portfolio career
This will form the foundation for future conversations on the topic.
Objective No. 1: Do Interesting Things
The first objective of a portfolio career is to do a mix interesting things.
For some, that may mean focusing on one company, market, product, and being the best at it. But for an increasing number of professionals, this means doing a great many things.
Until recently, doing many things was only available to those with decades of experience. For example, a seasoned c-suite executive who, in addition to being CFO, serves on the board for 4 companies and is an advisor for a non-profit.
What an awesome work-week for that person. Exposing themself to different idea, people, products, technologies, markets, and more. This person is exercising their whole brain and is empowered to lean into areas that need it while other areas do not.
So the first objective of a portfolio career is to achieve this state much sooner and to work on a variety of interesting things. Rather than waiting till you are a seasoned executive, you find niches where you can add value and provide services simultaneously.
From the professionals we have spoken to about this new career framework, we have heard significant benefits for each company within the portfolio. There is a network effect, connecting people and opportunities more seamlessly. There's the cross-pollination of ideas and experiences to realize better outcomes faster. And there's a genuine excitement that comes from having a healthy mix of projects.
This is possible through a portfolio career.
Objective No. 2: Take Big Swings
The second objective is more strategic.
It focuses on exposing oneself to 'big swings' while mitigating the inherent risks of doing so. Many of us have worked for startups, taken a pay cut for equity, and then had that equity turn to zero. It's not fun. Others have experienced massive gains taking that approach, but that is the minority, because it takes a miracle for a startup to be successful and for you to join it at the right time.
From product to management to funding to demand to competitors, these parts need to come together perfectly for your equity to be worth something. A portfolio career enables you to have advisory projects across a range of high-growth companies. You provide your skills and experience in exchange for a small amount of ownership or the right of first refusal when a job opening is available.
This approach can provide access to significant gains should the startup be successful and you are able to assess the likelihood of success while you advise them.
Objective No. 3: Mitigate Against Job Insecurity
Everyone has seen layoffs spike in recent times.
In March and April 2020, for example, there were over 22 million layoffs in the US alone.
Stories about layoffs spread like wildfire through the media, raising concerns about the health of the economy and even the health of America at large. I'd like to think they are rare occurrences, but they are not.
About 1.5 million layoffs occur monthly in the US, and over 200,000 people file unemployment claims each week. If you have been through a layoff, it's not fun for most people. It can be challenging to find work again, and you may be forced to take a pay cut, incur significant insurance fees, and more.
An objective of a portfolio career is to mitigate the impact of layoffs by providing other income streams, so you are not entirely stuck and using into your savings to make ends meet when it happens.
It is hard to argue against these objectives. Safe to say that most people are attracted to working on various interesting things, taking big swings, and mitigating the impact of layoffs.
But what is a portfolio career exactly?
The Definition
The definition of a portfolio career is having a series of different but interrelated marketable products or services that generate income independently, create synergies where the total is greater than the sum of parts, and responsibilities can be balanced in a way that DOES NOT compromise the success of any of your clients. The last part is very important - a portfolio career is not about neglecting clients.
The first thought that comes to people's minds when it comes to multiple income streams is real estate, and while rent may be an income stream, it's not a career per se for most of us.
I'm talking more about career variety. For example, someone that:
- Provides hands-on consulting services; and
- Advises companies on strategy; and
- Offers online digital courses; and
- Runs a profitable podcast
Or, someone that:
- Runs a boutique agency; and
- Hosts events and conferences; and
- Runs a profitable newsletter
Individually, these are potential careers. But together, they form a powerful portfolio that feed off one another, creating opportunities and synergies beyond what would ordinarily be created.
Typical Routine
At this point, you might be thinking that a portfolio career is a good fit for you. But before you take the plunge, let's talk about the typical routine for someone pursuing this career path.
Much of what it takes to build a portfolio career is about learning skills, gathering experiences, and productizing them. So, skill-building and product-building must be part of your standard routine.
A typical week is structured around the needs of your most significant project (or largest client), followed by the next most significant project. Continuous and objective prioritization is essential.
On Monday morning, before the day starts, you plan every hour of your week. This takes time when you have a portfolio. You must identify specific outcomes you're looking to achieve and when you plan to achieve them.
You think about what your client's priorities are and what you can do to assist with them. Help them see around corners. Share ideas and breadcrumbs. By the end of each week, you want to have exceeded their expectations in quality and quantity of work.
In other words, plan how you will always add massive value.
Then, you establish a meeting cadence. Confirm your regular check-ins, ensuring they do not clash with one another (which can be difficult). It's important to set expectations early around timeliness and ways of working to build momentum quickly and maintain it.
Then, you run through the week, focusing on high-value tasks and outcomes, timeboxing your focus and energy, and regularly updating your stakeholders on progress and escalations.
You also want to build and spend time with your support team. Ensure they feel heard and encourage them to find and implement efficiencies.
Your support team might include someone who can build slides, financial models, or pitch decks. You might need an attorney and business advisor as well. Ideally, these teams are spread around the world, taking advantage of time zones so that someone, somewhere, is working on something you need while you sleep.
The Risks
While a portfolio career may seem attractive, it's not for everyone, and here's why -
- The work can get extremely busy. Your mentality needs to be such that you will not let anyone down, and while you try to spread deliverables over time, sometimes that's not possible, and you have to dig deep to get it done. Of course, that may be the case for any kind of career; it is certainly something that people who pursue portfolio careers will face no matter what. If you don't handle pressure well, this is not a career you should pursue.
- Existing employers may consider your portfolio career disloyal and distracting. Part of this may be true, in which case you need to reassess your choices, especially if you need to improve at multi-tasking. Other times, your employer will just have a traditional view of work where putting in face time and being a die-hard company loyalist is the only way to be. Be sure to pick clients that support your approach and be transparent with them.
- You may spread yourself thin, losing skills you once had in a particular area. This may result in you becoming a generalist. Consider whether this is a risk for you or not.
- You may invest time and energy into opportunities that collapse into nothing.
While each of these risks are real, there are mitigation strategies that have worked. We will talk about them another time.
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