Earlier this month I bought a copy of Courier Mag to revel in the stories about those brave enough to pursue their own adventures and ‘become a tablescaper, ‘launch an online interiors marketplace’, ‘build a gender-neutral underwear brand’ and so on.

The message is clear: there is no shortage of ways to make your own living and inspiration is everywhere for those who are ready to shift gears with their career.

I can’t help but resonate with the subtitle’s message that those who do, may just change their life. My life has changed pretty drastically since I quit my job in 2019 in so many ways including increased confidence, happiness, health, and depending on the month, wealth.

But I also don’t believe you need to build something as newsworthy as the businesses in Courier to be considered entrepreneurial, or to reap similar rewards.

This post will explore what having an entrepreneurial career path involves and offer some principles and frameworks when charting your own — because more and more people continue to do so each day.

Entrepreneurial Careers Defined

Every job I have had since leaving university has been future-facing: headhunting tech/digital executives, building startup accelerators (my job title was Head of Entrepreneurial Talent!), hiring teams shaping the future of health & transport, and today, coaching people to create the future of their dreams.

Ironic that I got a first class degree in History.

Does my focus on the future of work make my carer path entrepreneurial or is it only since quitting my job to be self employed that it counts? Was my youth selling sweets on my local street corner, babysitting, or selling clothes on eBay part of this master plan?

Personally I would never have described myself as entrepreneur (and not sure I would today either) BUT do believe that I have maintained an entrepreneurial mindset.

You too probably have one of these.

A mindset of being someone who sees possibilities and does something about them (not just talks about it), who solves problems and brings new creations or changes into the world.

Being entrepreneurial is less about the source of your income each month. I believe it is more the fact you self-select yourself and take advantage of the plentiful tools at your disposal that are ready for the taking by those who wish to make an income, an impact, and try something new.

It is the fact you are willing to put yourself out there with no guarantee that your efforts will be appreciated or succeed.

The longer I work in this field the more varied my definitions of an ‘entrepreneurial’ person become. Many of my private coaching clients have a salaried job, but they work so hard on their own creations in the evenings and weekends in the hope of building towards a different future. Some clients are happily employed but have creative projects they want to put into more customers’ hands. Some are the more traditional ‘founder’ types who run a business with a brand, team and are backed by investors.

I attempted to explore the entrepreneurial paths last year: What entrepreneurial career paths are available today? which you can read or just check out the table of some definitions provided here including how they typically fund themselves and what monetisation methods apply.

It is precisely because of the wide-ranging definitions within entrepreneurial career paths that I have found describing what I do so difficult. For a long time going with the description ‘founder coach’ then later realising this resonated with a small percentage of my audience. Now I define it as coaching for ‘entrepreneurial professionals’ — helping people in such paths to decide and plan their next career pivot or business idea. There are many of you in entrepreneurial paths (or aspiring to be) who need help figuring out the messy middle bits in between employment/self-employment, how to start, pivot or quit something, or align on your biggest career and life goals.⁣

Tell me — as this newsletter evolves from just ‘founder’ advice and into the realms of the ‘entrepreneurial career advice’ — where do you sit?

In one click you can help shape the future of this newsletter and ensure I am tailoring it for you.

Where are YOU at in your entrepreneurial career path?

• 🙌 I already have my own business

• 💪 I am working towards having my own business

• 🤘 I work in related fields or have a general interest in entrepreneurship
  

PS I used a FeedLetter poll so you can ignore the screen that tells you you rated this post :)

The Great Resignation → The Entrepreneur Revolution?

Aside from my own interests, the topic of ‘entrepreneurial careers’ in a post-pandemic world is taking over public consciousness like never before. Increasing numbers of people took out their workplace dissatisfaction in the form of handing in their resignation as the ‘Great Resignation’ went underway.

So does this mean that more entrepreneurs will inevitably exist in our future? Have those quitters all started their own businesses? Or did they merely find better roles?

Whilst the Great Resignation might be better branded ‘The Great Rethink’ (many took up new jobs) I still argue that the future looks very different for employment.

It is no coincidence just so many people said ‘shove it’ and walked away from employers — discontent with poor work life balance, outdated working practices, lack of inclusion, progression or a whole host of other gripes. We have more choice about how we make money in today’s world.

Going forward there will either have to be a big shake up where employers make significant changes to attract talent or we continue to see more people pursuing a path on their own.

I believe the latter is more possible.

Such possibility seems feasible when you consider factors such as globalisation, automation and AI. Whilst in the past the barriers to entry for businesses were high and meant that companies could build defensible moats around their operations (supply chain, infrastructure, IP and geographic borders) today these no longer apply.

Businesses are getting smaller and as this happens they will exist with fewer full time employees and a roster of freelancer/contractor/consultants to support them. There is a real possibility that many of us are individual entities and the infrastructure for the self employed improves too — in the form of other businesses whose product services self employed workers’ needs around their financial, insurance, wellbeing needs etc.

Soon talking about an ‘entrepreneurial career’ could feel outdated. In the same way we used to describe companies as having a ‘digital’ team less than ten years ago…. now almost all operations are digitised in some way.

Perhaps we are all the ‘entrepreneurial spectrum’ and this spectrum is a moving target too as more people end up on it — whether voluntarily or otherwise.

The ‘Career Ladder’ in Your Entrepreneurial Path

The term ‘climbing the corporate ladder’ traditionally made a lot of sense — you start at rung number one (intern grabbing coffee) and if you do well, receive promotions and pay increases. You climbing the top and sit in your corner office with the skyline views, watching your bank balance and pension pot balloon until one day you are done climbing and get to sit back and enjoy the fruits of your labour.

Sounds kind of nice actually.

But as we all know, such promise rarely exists. Today we move jobs more, pensions are rarely reliable, and many of use reject corporate life to become the beneficiary of our careers.

As your own boss you have to figure out how to grade reward and grade yourself.

So what is this career ladder?

I have heard it called the ‘pathless path’ aka a path without direction or rules.

However you can define your journey in stages and gauge whether or not you are progressing. I wrote The Practical Creator post last month exploring how this path looks for creators.

But what about everyone else?

What about the freelancer with a client base — is progress more clients?

What about the influencer with an online audience — is progress better paying brand deals?

What about coaches and consultants — is it growing in status?

The answer depends on what you want. On where you are going. On what you want to learn and improve upon. But rather than leave you hanging here, I will offer two potential frameworks to judge your success on your entrepreneurial career ladder.

Framework 1 - The Pursuit of Mastery

In ‘So Good They Can’t Ignore You’ Cal Newport describes how the most enviable careers (the fulfilling ones people love) bring the following three components:

1. Autonomy – sense of control over your time

2. Competence – the feeling that you’re good at your work

3. Relatedness – connecting with other people in the process

His definition comes from in-depth research into the happiest and most successful people at work. He claims they achieve this status not based on how ‘passionate’ they are in their field, but to the extent of mastery they have achieved.

Mastery as you can imagine is achieved through practice — commitment to a craft and getting better over time. The rewards granted to those who master their craft are increased levels of autonomy, competence and relatedness. You don’t have to be an entrepreneur to realise these benefits but often what makes people want to pursue the entrepreneurial path are these benefits. So see them as a sign your entrepreneurial work is succeeding.

Framework 2 - The Wealth Creation Ladder

In his 2019 essay, Nathan Barry describes the roadmap to wealth creation as being the inverse of whether you are trading your time for money. From an hourly wage all the way through to building a social network he charts the path of creating leverage through these career paths. I recommend a read of the full piece.

Nathan’s post accurately explains why I have self-employed coaching clients for whom it is not enough that they are their own boss, since they want to build something that belongs to them.

Something independent of their client work which they can have full control over in terms of how and when they work on it. I have many clients who operate a client-facing freelance business but have hired me to help them build a new brand, perhaps selling to consumers rather than businesses. This is moving to the right on the ladders.

Read the ladders below (you don’t have to go through each rung before you can progress, however you do learn new skills at each, which help you to progress).

Take the parts that resonate with you.

However don’t be fooled. Just because you are successful moving across the rungs and building a SaaS business will not mean you are necessarily more happy than if you were running a 1-1 services business. For many people the struggles that come with wealth creation outweigh the benefits — more stress, complexity, challenge and so on.

You need to chart your own definition of a ladder you actually want to climb.

In my own path I have seen first hand a recent benefit of moving across the ladders and achieving mastery.

In my travels this year I have been doing the ‘digital nomad’ thing and will have lived in four continents by the end of the year. Today I write to you from Las Palmas Gran Canaria and I can safely say this opportunity is the hugest privilege that I am endlessly grateful for. You don’t have to be an entrepreneur to experience such benefits. Many of the people I have met here have jobs, but I recognise that I have another layer of freedom and flexibility, being privileged in not having to make a request from an employer, having to work during weird hours to match time zones or be penalised for going against office cultural norms.

I therefore have the autonomy Cal describes and I do not charge by the hour for my services. This year I have even created a productised service (The Talent to Money Bootcamp) with the next cohort starting next month. The first one finished yesterday and I will share more about it soon — it was ace. You can apply to join if you want the support and tools to start your journey moving across these rungs and building something of your own!

Thank you as always for reading!

Ellen Donnelly, Founder + Chief Coach, The Ask.

I’ll be back in your inboxes in two weeks’ time and until then you can check out more about my own business The Ask and how I support people deciding on their next career move or business idea. Book your complimentary consultation here.