What entrepreneurial career paths are available today?

Understanding the nuances and various types of entrepreneurship afforded by the internet, and how to go about choosing the right version for you.

Hi folks

Great to be back in your inboxes again and a big hello to new subscribers since last post :)

Today we are reflecting on the term ‘entrepreneurial’ because not only does it get thrown around a lot it is also one I use to describe my audience. That’s you!

It’s a bit of a marmite word too, I notice.

As far as I see it, entrepreneurial career paths are more nimble, involve greater risk and personal autonomy. They are about taking the steering wheel and driving to your own destination rather than someone else deciding for you.

As you consider which entrepreneurial career paths are available to you’ll cover the following bases of the discussion:

  1. The world itself — we are living in a more entrepreneurial context than ever, and why that is

  2. Understanding the nuances to the types of entrepreneurship now available

  3. Defining your own version of success in your entrepreneurial path (and factors I’ve considered in mine)

Image Credits in this post

The World We Live In

In todays’ world we are more likely to work for (or build) early stage companies than ever before.

That’s because in the past it was harder to build companies. This created less competition meaning there was simply less companies in existence, and those that were successful tended to be bigger and stick around for longer (think manufacturing, retail, pharmaceuticals, foot, automobile etc). The barriers to entry were higher and so companies could build defensible moats around their operations which were just harder to replicate. Moats such as their supply chain, infrastructure, IP and geographic borders.

For employees, bigger companies mean more opportunities for progression and stability and can present a lifetime of employment in the same place.

In recent years, shifts in technology, globalisation and cost of goods and labour have made it easier than ever for new entrants to take advantage of market opportunities and disrupt entire companies, and even industries.

Nowadays, in general, the ‘atom’ of a company has become smaller. Most businesses will do one core thing and use external suppliers/outsourced providers or freelancers to fill in the gaps. An agency may offer a service to its clients in house, but rely on providers for their payroll, HR, design, marketing, IT and lead generation.

This creates more, but smaller companies, in general.

Attrition is higher in small businesses since people run out of career progression or get squeezed out due to budget cuts and once people have worked in small businesses enough to see what’s involved, many decide to branch out and start one of their own.

You might feel like every man and his dog has their own business today? You could be right.

Culturally speaking entrepreneurship has become more enticing. More people are doing it, and more people are talking about it.

In fact, it’s even become a necessity for so many people in the last year especially as huge swathes of workforces in industries affected by COVID-19 have found themselves needing to start a business through lack of employment options.

The Various Flavours of Entrepreneur

The beauty of all this change, and small companies popping up left right and centre is the choice of how you define your own entrepreneurial career path.

You’re not limited to only building the same business thats existed in your family for generations, or being the next Elon Musk just because that’s the immediate association with entrepreneurship.

There are more.

In keeping with this newsletter I’ve focused on types of entrepreneurial paths that the internet has helped to enable.

This means you won’t see types along the lines of franchisee, beauticians or shop keepers which are valid nonetheless just outside the realm of this discussion.

Internet-enabled entrepreneurial paths

Below are nine types of ‘entrepreneur’ you could become thanks largely to the power of internet in opening up clients who live outside your local area, to network effects, and to the platform we are all afforded by the internet to reach thousands of people.


Name: The terminology I feel best describes this path

Definition: Self explanatory, but my own my definition

Funded: Typically how they get started (external investment vs revenue based sales to fund themselves)

Sales: Where their money comes from, typically.

NB: Many people will be both and, so they may be an Indie Hacker and Creator. Or a Thought Leader and freelancer.

Some more resources to learn more about these types of entrepreneurial paths

Defining success in your own entrepreneurial career

What fascinates me the most about these newfound forms of entrepreneurship is how there is no roadmap for success. You are left to define it on your own terms.

For a creator, do you measure growth via audience metrics, profit, or doing better more creative work?

For a freelancer, do you seek higher day rates, bigger brand clients or more freedom and flexibility?

There are no right answers to these questions. It starts with really knowing yourself and how you are wired and what you value. What will motivate you each day, year on year?

What many struggle with in these paths is the lack of validation.

You don’t have a boss saying ‘great work’ here is your bonus! Unfortunately.

I recently caught up with an entrepreneur friend, Freddie. In 2018 I helped him in the early days of his business, whilst I was working in a startup accelerator as Head of Entrepreneurial Talent.

He said the challenge that many people don’t appreciate starting out, is that there is often so little reward building a business, in that you can go for so long with almost no validation. You just keep going and adapting, and you will eventually get there but so many people fall off before this point because they can’t deal with that aspect of the grind.

I believe some businesses will get you that validation quicker than others, like services businesses with happy clients, or side-hustling where you can see huge progress whilst keeping the safety net of a job and earning dual income.

But others are a slog that require you to show up day in day out and do the work without money or followers to show your metrics. You are improving, through learning, but often without a quantifiable end result.

Eventually you can make it happen, as Freddie said. He has raised hundreds of thousands of pounds in investment for a tech business around sports, his ultimate passion. But he has lived off a minimum wage in the process. He’s on his third co-founder and product iteration.

The answer to which entrepreneurial career path is for you is determined by the degree of risk you can afford to take financially, by the skillset you can turn your hand to and make money from, and by your ability to show up and share your work even when no one seems to be listening.

I’ve been ‘putting myself out there’ a lot over the last year building The Ask. Whether on IG stories, this newsletter, or creating events out of thin air. Fortunately my feedback loop has been quite quick, and I’ve been able to support myself with some talent consulting freelance gigs where the months have been slower on coaching sales. If I judged my success on my monthly income alone it would be tortuous since that varies so much. Some months I’ve earned 4x what I was earning as an employee, other times, just £80 in revenue that entire month (losing money due to fixed monthly outgoings in the business).

So the road is long and rocky, but it sure is rewarding.

Starting a company is one of the biggest self-development journeys you can go on. Dusting yourself off at the end of a day of rejections or no progress and doing it again the next day is not for the feint hearted. But the rewards are available to those who make it work. Freedom, flexibility, financial gains, creative work, doing something you love… these are very real tangible outcomes that draw so many to entrepreneurship despite its challenges.

Through recent months I’ve realised my heart really lies n helping individuals start their own companies, whether that’s alongside a job or fully-fledged entrepreneurship. 100% of my current clients are new business owners.

This is my passion and purpose and I’m so grateful to call it work.

The time I felt the lowest in my career was not knowing what my purpose was, where I was headed, or when, how, and if I could ever channel my skills within the context of a job.

My favourite activities — coaching, writing, speaking, selling, collaboration — these were not available to me in a full time position as far as I could see. I knew I had to create a business around myself and what I loved.

This is the journey of building The Ask which I wouldn’t trade for anything. It’s the journey of figuring out where the money is coming from, what the branding is (new one live now!) who my ideal client is, and what deep work should I do daily that will also bring value to the world.

The mental load on a founder is a LOT. You go around in circles about your idea, purpose and what actions to take next.

My client Catherine said through coaching she’s learnt to “manage the roller-coaster of emotions of entrepreneurship” and that she has “more space to breathe and have set clear goals truly aligned with my long-term vision and mission”.

If you’re reading this with an urge, excitement and passion to make your entrepreneurial dreams come to life, whether as a side hustle or main gig this year, I’d love to invite you to a complimentary no obligation consultation for coaching.

Coaching would involve  going deep into understanding your unique talents, strengths, and opportunities for turning passion to profit. To then working out where your money will come from, and how to continually get stuff done and keep a positive mindset throughout.

That’s all for this week.

I hope you learnt something about the complexities and nuances of pursuing entrepreneurship. If you liked today’s post let me know with a little <3 (I need the validation remember ;)) or get in touch if you’d like to learn more about how I can support you with my ICF accredited coaching qualification and decade experience working with startup talent.

See you again in two week’s time.

Your Coach,