The Angel Investing School provides me with unique access to professionals. After speaking to hundreds of entrepreneurial professionals, I’ve developed a strong understanding of why so many employees want to become entrepreneurs. My work allows me to create a safe space to discuss economic empowerment, wealth creation and business building. Increasingly it has become clear to me that everyone’s an entrepreneur.
I’ve lost count of how many people I have met inside of companies who have some ‘side hustle.’ From someone who is an accountant in their 9-5, who bakes brownies in their 5-9. Or a lawyer who delivers confidence workshops to empower women outside her day job. I am not one to shout out yearly predictions about the future each year but one trend I am bullish about is the move towards portfolio careers.
What is a portfolio career?
A simple definition of a portfolio career is a career where you do several part-time jobs alongside each other. For example, you could work as a tutor two days a week, and teach in a school three days a week. Or you may DJ two days a week and work as a software developer another two days a week then have a three-day weekend.
I believe COVID has accelerated the trend towards portfolio careers because so many of us were on a search for more meaning and purpose in our work. At the same time, we wanted the financial freedom and time to do work we love with whomever we want. This is a luxury for most and a pipedream for others.
Today my portfolio involves writing, teaching, coaching and speaking about entrepreneurship and investing. The Angel Investing School is a part of that portfolio for me. This career enables me to have more agency over my lifestyle. A commonality I found with all employees who have ambitions to transition from employee to entrepreneur is the thought of designing their ideal lifestyle.
What would your portfolio career look like?
The road from employee to entrepreneur
Just the other day, I was speaking to a Cloud Engineer at a big tech firm that has started providing fractional CTO-as-a-service support to early-stage startups. She mentioned her ambition was to replace her salary. I told her that was a crutch and that instead, she needed to consider her minimal viable income, i.e. how much does she need to earn to cover her cost of living?
Once you have found your niche and saved up a financial runway, what next? Before anyone quits work to work fully on their business, I advise 4 key steps:
- Figure out who your target customer(s) are
- Decide on what product/service you will use to solve their problem
- Build an audience
- Test language, product/service and willingness to pay with this audience
I’ll save the walk-through for another post.

Not everyone needs to become an entrepreneur
Let’s call a spade a spade. Modern culture glorifies entrepreneurship, so too many people underestimate what it takes to build a sustainable business they can live off. It is hard work!
Entrepreneurship is a team sport, not everyone needs to be a founder. For every founding team, there are dozens, if not hundreds of employees they hire as they grow the business. So many of the experienced operators who invest alongside The Angel Investing School often join a scale-up and make money from selling their shares. There is value to being an employee (operator).
Your expertise and network as an operator make you an invaluable angel investor for an early-stage startup. Your battle scars are valuable lessons learned for the next generation of budding entrepreneurs. Growing up in a good company means that you are getting paid to learn. For founders, ex-employees are a great talent pool to hire from too. Let’s not fall into the trap of undervaluing a good career, good income and stability. Whether you are an entrepreneur or an employee there will always be pros and cons.
If you want a hand on this journey, consider joining The AIS Membership. We have dozens of business owners and entrepreneurial professionals working together towards economic empowerment, wealth creation and leaving a legacy.
