Building a Portfolio Career on Upwork

Stephen Bates
6 min readNov 17, 2023

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Lately, I’ve been reading a lot about the growth in the ‘Gig Economy’. I’m reading articles from industry thought leaders speaking on the importance and value in having a ‘Portfolio Career.’

Its rise in popularity is similar to the way a playlist on a streaming service has replaced the old-fashioned radio station. In the past, you had to tune in and listen to whatever the DJ played, just as the majority of people stick with one job or career path. But now, with a Portfolio Career, you can become the DJ of your own professional journey, creating a dynamic and personalised mix of gigs and opportunities that suit your unique talents and interests.

The Gig Economy is reshaping the world of work, and workers are embracing the freedom and flexibility it offers. McKinsey states that the Gig Economy refers to ‘refers to the workforce of people engaged in freelance and side-hustle work.

The OECD forecasts that by 2030, half of all professionals will have portfolio careers. Ben Legg from the Portfolio Collective says ‘a portfolio career involves monetising your skills in many ways and having multiple income sources, rather than a single job at one company.’

Some individuals are drawn to the gig economy due to its potential positive impact on mental and emotional well-being.

Well, one might ask, why has there been such a shift in workers’ mindset towards the gig economy and building portfolio careers? It can be attributed to several compelling factors, driven by the evolving landscape of work and a changing economic environment.

  1. Desire for Autonomy: Workers today increasingly value independence and autonomy. The gig economy provides them with the freedom to choose when, where, and how they work, which is a powerful draw in a world that increasingly values work-life balance.
  2. Economic Uncertainty: Traditional job security has waned in recent years. The gig economy and portfolio careers offer a degree of risk mitigation. With multiple income streams, individuals can weather economic storms more effectively. This has been highly evident across the Software & Technology industry over the last few years.
  3. Global Connectivity: Technology connects workers to a global marketplace. Freelancers can tap into a vast client base, and portfolio workers can collaborate with international partners, expanding their opportunities. Only 55%–65% of the world have access to the Internet today. Solutions such as Starlink and Kuiper will dramatically change the world when it comes to work opportunities and economic growth, tapping into a whole new world of job opportunities.
  4. Impact on Well-Being: Some individuals are drawn to the gig economy due to its potential positive impact on mental and emotional well-being. Flexible work arrangements can reduce stress and improve overall job satisfaction.
  5. A Paradigm Shift: A generational shift is taking place, with younger workers challenging the traditional 9-to-5 model. They prioritize meaningful work, personal development, and lifestyle over traditional corporate structures.
Photo Credit: The Portfolio Collective — https://portfolio-collective.com/

This image really caught my eye when I first saw it. It’s the feelings and actions I’ve been working towards over the last few years. When I read Hanna Larsons article 💰 Here’s How You Start Building Multiple Income Streams, it was the first time I saw ‘Portfolio Career’ discussed in detail and everything sort of clicked in my mind.

Now, as we explore the evolving nature of work and career choices, let’s delve into practical tips for navigating the gig economy. One platform that has become a hub for freelancers and those seeking flexible work arrangements is Upwork. But why Upwork, and how can you make the most of it in building your portfolio career?

After meeting my mentor Daniel Yamoah a few years ago whilst working at Salesforce, I found myself deep in reading personal development, finance and investing books on his recommendations. I was new to it all. It amazed me. It took over my focus. I couldn’t think of anything else. I was so inspired by my new learnings I wrote an article on LinkedIn 3 years ago sharing my new learnings and routines. (You can read it here: My 5 Month Review…)

In the journey of life, ups and downs are inevitable, and things don’t always go as planned. One of the best pieces of advice Daniel gave me was:

‘When one door closes, another door opens.’

Reflecting on these wise words, one piece of advice I like to give people looking to build a portfolio career from scratch, especially on Upwork, is to Drop the Ego. Ryan Holiday in ‘Ego Is the Enemy’ defines Ego as “an unhealthy belief in our own importance. Arrogance. Self-centred ambition’.

My view? Take on jobs and opportunities that you’re over-skilled for. Over-exceed and over-deliver on expectations. Build credibility. Even though you might have in-depth expertise, adopt a beginner’s mindset. Deliver value without being overly concerned about personal importance or self-centre ambition.

Looking back, saying yes to the opportunities where I was over-skilled was one of the best decisions I made and is the strategy I followed to make my Upwork profile completely inbound.

A personal story I’d like to share: After being made redundant by one of the fastest growing startups globally an opportunity came up to work with Ireland’s largest and most popular startup incubator programme. The role was a business development associate, the duties and descriptions were entry level requirements. After thinking about it and discussing it with a close friend. I concluded that the chance to work with six determined startups currently in the process of developing their businesses and go-to-market strategies, while also participating in the accelerator program, held more value to me than going back and finding ‘one main job’ and ‘working for someone else’.

‘When one door closes, another door opens.’

I was now working side by side with hungry and passionate CEOs. Sitting in sessions with industry experts. Working together on business development strategy sessions. It was all starting to click in my head. I had a lot to give here. I had just spent years working on one of the highest performing teams in Salesforce. The startups needed advice and I had it. I ended up spending my time on the accelerator programme working with each startup directly on sales strategy which included building net new pipeline, how to close deals, creating sales processes, handling objections, uncovering pain and challenges, creating mutual close plans, understanding how to create compelling events — the list goes on.

These were all things I knew well but unfortunately I was guilty of taking some of that knowledge for granted. It was only speaking to these startups that I realised how valuable these insights were. It amazed some of them. The feedback was great.

Naturally, my mind starts to think about how I bring this forward...

This thinking phase put me in a situation where I realised that I no longer want to do ‘Traditional Work’. Fast forward 12+ months, I’ve founded a company, I’ve advised numerous startups and coached young ambitious professionals and more recently have put a lot of work into building out my Upwork profile where I now solely receive all my work through inbound.

Drop the Ego.

In my upcoming posts, I will be sharing tips for building and optimising your Upwork profile so that you get so many inbound leads you can’t handle them…

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Stephen Bates

I talk about building a portfolio career. I help early stage companies with building net new revenue and executing business development strategies.