Money, time and growth: how to plan a portfolio career

Money, time and growth: how to plan a portfolio career
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In a world that we don’t understand but need to explain, anxiety often acts as the driving force behind our decisions. Uncertainty can paralyse us, especially with career choices. Perhaps it’s that awareness of uncertainty that makes people either question or delay the inevitable transition to self-employment.

But you can’t let the fear of the unknown hold you back. 

Millions of people around the world are stepping boldly into the portfolio lifestyle, and that’s because they learned to embrace the unknown and make peace with the anxious voice in their head that rattles through a thousand negative scenarios.

In my five years as a portfolio professional, I’ve had my doubts too. I’ve often asked:

  • Did I make the right decision?
  • Would I have more money if I stayed in full-time employment?
  • What does the future hold for me?
  • How do I plan for it?

That last question carries the greatest weight because it’s rooted in hope. 

In an absurd world, hope is a powerful tool

Hope for the future

My hypothesis is that there are two kinds of hope – one based on entitled belief and one on diligent objectivity. In the first kind, one believes that “things will work out for the best” in a state of active imagination and passive observation. In the second, having exerted every ounce of effort possible in the path to a defined goal, one resolves that “I have done what I can. Now, I must wait.” Planning separates the two.

I picked a portfolio career because it allowed me to keep learning, hone my craft, focus on measurable targets and align my energy with my routine. Fierce focus and constant improvement (supported by physical and mental health) is the only real competitive advantage, at least for knowledge workers, in today’s skill market. From that lens, a portfolio career is a smart choice because you can learn faster. Also, a portfolio career gives you control over your day, aligning your actions with your needs and wants – but it’s not without its challenges.

Now, I’ve been doing this portfolio career thing for a while and I still have those questions. I understand the journey is more important than the destination, but tell that to the taxman, the landlord or the bank, and watch your philosophical shield crumble in the face of fiscal realities. Contrary to popular belief, hope can be a valuable tool, but it’s not a strategy. It’s impossible to take charge of planning your portfolio career if you don’t have suitable systems and goals in place.

So at a recent Portfolio Collective career check-in event, I asked Ben Legg (CEO and co-founder of TPC) this question: How can portfolio professionals create long-term plans that allow them to scale and develop whilst generating income? 

Ben’s response offered me direction, clarity and a simple approach for the next 12-18 months. The rest of this article details his answer supported by excerpts from my experience.

Money: managing your finances and growing your income

Money managing your finances and growing your income
©The Portfolio Collective 2021

Time and money are the two axes we use to plot our transactional lives, and ensuring a surplus of both can free up space for thinking and strategic growth in a portfolio career. Let’s start with money, given that financial security is often the primary anxiety we face.

1. Earn more than you spend and have a pension plan

While a relatively simple idea at first glance, “earning more than you spend” differs from “saving more than you make”. Satisfaction as a portfolio professional demands a lifestyle that matches your vision. Once you list your wants, needs and dependencies, define the amount you must make each year before adding a savings target. 

As a freelancer, you won’t have the benefit of pension plans – so build your own. Even having a small emergency fund can ease your financial anxiety. When I first moved to a consulting setup, I took a 30% hit to my income that I could offset with 16-18 months of good financial behaviour. With around a year’s living expenses available to draw on in emergencies, I stopped worrying about monthly income. Instead, I focused on doing satisfying work that kept clients happy.

2. Build long-term relationships with startups

Your skills are defined, effective, valuable and flexible – all of which are gold for companies looking to build their footprint. Find startups you care about or genuinely believe in before investing time in a deep relationship. Every portfolio professional is a startup anyway, so you’ll find it easy to relate to founders. Think of this as your compounding moonshot, one that could pay off handsomely. 

You can monetise your arrangement through stock options, sweat equity or even a higher stake in the company for more involvement, assuming immediate cash flow isn’t your priority. Selling your hours for a fee is only one income source, and startup relationships can help you expand your revenue streams.

Foster relationships with startups

3. Consider creating your own startup

A portfolio career is often the precursor to a full-blown startup. Portfolio work allows you to work with clients on several challenges, enabling you to gather precise and rich market insights. Once you understand what people need, you can build on it by eliminating friction, adding value or expanding insights. If it is hard to see the potential for a company at first, consider documenting your processes and bunching similar client issues into service categories to set the foundation. 

Even if you’re an independent consultant in a high-touch business, there will be parts of your service which you can automate. Find where these touchpoints are and either automate or delegate them so you can deliver high-value work without distractions. Stay consistent, and you will soon offer an easily recognisable value proposition that attracts clients without your involvement. Always keep an eye out for potential partners to build your idea – the TPC community is a great place to find those collaborators.

4. Create passive income

Assets, investments, stock options, courses, books and intellectual property are just a few ways to drive passive income, but several great ideas exist. Creating a course or writing a book can be an excellent way to showcase your expertise while reaching a broader customer base. If you have a spare room or property to let, you could also run a property rental, Airbnb or co-working space.

If you’re not in a hyper-specialised field, look to place several bets to improve your odds of success. For example, I’m a corporate communication consultant interested in writing, with a passion for creative arts and a desire to build a coaching business. So my approach includes consulting, podcasting, running learning sessions for university students, hosting events, writing poetry in collaboration with visual artists, making music and lending my voice to creative projects. 

Think of your own combination and get started on a few ideas. Prioritise diligence over reason, at least when you’re experimenting, and see how the results might surprise you. 

Time: investing in your professional growth

Time investing in your professional growth
©The Portfolio Collective 2021

Much like a lobster enjoying a hot bath before a butter-drenched service, we are notoriously impervious to our own decline. Portfolio careers are fluid and need you to dictate their structure and trajectory. How well you do this depends on your relationship with time. In this regard, time is our most valuable resource, but only if we use it well. Here’s how you can plan your time to ensure that your portfolio career doesn’t just stay on track, but grows with you.

1. Spend time with smart people in areas different to yours

Our personality is a product of thoughts, genetic code, experiences and environment. Being intentional about the people you surround yourself with (both online and face-to-face) can be a powerful way to expand your mind. 

Seek people of all sorts and have deep discussions with them. Find out what makes them tick and how they make decisions before discovering how you can get a sense of their worldview and sources of learning. You don’t have to be heretic about the immediate impact, but stay consistent and you’ll see your imagination grow. 

In my case, I break networking activity into broad, interactive and hyper-focused efforts: my podcast (broad) is one way I reach out to people who interest me; I’m particular about who I engage with on LinkedIn and thriving communities like The Portfolio Collective (interactive); I occasionally reach out to experts in my field or others for a skill barter or request for a brief discussion (narrow). Avoid spreading yourself too thin and instead focus on a few sources of interest at a time. I constantly have to remind myself to slow down, which, while challenging, has always helped. 

2. Stay up to date with your industry and interests

The internet has decentralised talent pools and democratised information, both of which need you to be on top of your game to have any chance of being seen as an expert. In my line of work, this pressure means constantly reading and keeping up with every trend. 

Supplement and contextualise your knowledge repository by staying up to date with significant developments in your field via Google Alerts or through high-quality subscription content. With content consumption, try to apply a just-in-time approach (what you need for a task or goal) instead of a just-in-case mindset (reading anything that might be remotely relevant to your plans or interests). 

Nothing is changing as fast as the media would have us believe. If it did, we’d live in a state of constant flux designed to erode our mental health. So again, start the process and stay consistent. Oh, and don’t read the news.

 3. Write extensively and deeply

Write a lot and make it a habit. Writing compels clarity, even if that means noticing the disparate threads that occupy your mind. Of course, when you first begin, your brain will throw creative tantrums to distract you from the pain of wrestling structure out of chaos, and that’s okay. Just like being distracted is the actual work of meditation, facing resistance is the work of writing or any creative pursuit. 

Yes, it’s difficult, exactly as it should be. As a professional ghostwriter, I work with several incredibly knowledgeable clients who put off writing because they can’t decide what to write about. Hiring a writing coach might be the most effective way of addressing the issue, but here’s a free hack for you DIY aficionados…


Think of what people often ask you and why they come to you for the answer. Consider the most frequently asked questions/topics and write them down. 


Use a tool like AnswerThePublic to see how people structure their queries on these themes. That should give you a few topic ideas – list at least three.


Pick the platform where your audience hangs out most and, critically, give yourself a deadline for your first piece.


Face your fears and publish your ideas.

The end goal is to post regularly on your website, but you can get there, eventually. And if you’re looking to get started soon, schedule a free call with me so we can discuss your content approach.

4. Build a bespoke body of knowledge that you can monetise

The bar for recognised and valuable expertise is very high. You can either take the unpredictable and stressful route of being in the top 1% of your field or use a smarter approach by developing a unique body of knowledge that showcases your individual experience and interests. 

Outside of work, I engage with philosophy, mental health, sport, culture and language, so my services use a blend of these disciplines. I run a podcast about lifestyle design and existential experiences, journal, train with a former professional sportsperson and mentor startups and professionals looking to write. With a desire for a breadth of experience, I’ve also worked in events, as a product sampler, university lecturer, communication trainer, marketing consultant and even a dancing bear for a candy company. 

I believe these experiences give me a different perspective capable of starting a range of conversations. This education bleeds into my consulting practice, allowing me to understand and have deep, trusting relationships with businesses and people.

Identify what people are looking for and build on it

To bridge the gap between monetisation and interest, you need to understand what makes people tick. Aligning your ambitions with demand will help you test your proposition faster while motivating you to keep going. It’s okay to believe that a mix of passion and purpose will give you satisfaction, but not at the expense of ignoring the reality of a capitalist market.

We’ve covered a lot of ground in this post, and I hope you’re better equipped to structure your portfolio career journey. While an important issue, know that it is not the only priority. In a life dictated by finiteness, the best chance of success involves taking care of your mental and physical health. Be kind, stay active and use discipline to provide you with the freedom to think. Focus, consistency and creativity won’t guarantee success (nothing will), but they will offer you the opportunity to enjoy the ride. Besides, you’ve already taken a chance, and what’s a better start than that?

Are you looking to get more in-depth insight on career growth and planning? Come along to TPC’s weekly Career Focus Workshop or join the next Career Check-in Let’s Talk event. You’ll be amazed by what you discover – I know I was.

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