Starting Your Own Business: A Woman’s Guide to Transition from Employee to Entrepreneur

The emotional toll of working in a job that is silently (or not so silently) killing you on the inside is the one topic that’s usually not shared around the proverbial water cooler at work. Honestly, if you knew how many of your co-workers were secretly plotting out their early retirement, who have a countdown timer on their desktop that reminds them how many days they have to muscle through before their dreaded boss retires, or who spend their lunchtimes (and a lot of their afternoons) scrolling for new jobs on the internet – the numbers would likely shock you. One solution many unhappy corporate employees consider is starting their own business.

Starting your own business is an increasingly popular route for many seeking to escape the confines of a 9 to 5 job and embrace the flexibility of entrepreneurship. This transition offers not just the freedom to work from anywhere, but also the unique opportunity to build something that truly aligns with your passions and desired impact on the world.

This article aims to guide you, the (potentially?) aspiring entrepreneur, through the critical decision-making steps to explore if entrepreneurship is the right answer for your career woes.


Understanding the entrepreneurial desire

Let’s be clear, quitting your day job and starting an entrepreneurial venture isn’t always the answer. “Wherever you go, there you are,” writes Jon Kabat Zimm. Take it from one who knows. When I resigned my corporate career at an international energy company in late 2002, my reasons for leaving weren’t all related to my role – many of the reasons were related to the confines of the traditional corporate workday and juggling so many new responsibilities as a new Mom in a new city with a new husband and a new house and a new … the list goes on. Suffice it to say it was a lot.

And what I learned, as I hung out my proverbial shingle as a communications consultant, was starting my own consultancy solved a few problems, but it created a whole raft of new challenges. 

One key thing to note: my own leadership of self that I eventually learned included things like: time management, boundary-setting, expectations of myself, expectations of others, project management and so on – all had lots of room for development, that I ended up learning in the self-employed work environment – and tools I likely would have learned in the employed one too, over time.

So, back to the entrepreneurial desire – what I see time and time again is that the people who make it as entrepreneurs are highly convicted in their passions, skills and desire to make a difference in their area of the world. In short, your heart has to be in it. Because, guaranteed it’s not going to be easy and there will be much challenge (and reward!) along the way.


Self assessment: identifying passions and skills

self assessment identifying passions and skillsSo, you’ve decided to start your own business. You’re going to go for it. What is the business you’re going to start? Many corporate drop-outs decide to turn their learned skill into a contracted or consulting scenario that provides them with time freedom, yes, but also often with the freedom to practice their craft how they want. They may want to see things done differently, know they’re here to make more of an impact on the world with themselves at the helm vs hiding behind a corporate persona, or want to serve a market they can’t fully serve – in the way they want –  where they are now.

Others dream of running a venture that has them live somewhere else – perhaps they want to start a B&B, open a yoga studio or develop a new concept service that they haven’t yet seen – or believe they can do better. Regardless of what you choose, know that passion comes first, having a nest egg or financial cushion comes second, and having an open mind comes third – be prepared to not know what you don’t know. It’s going to be a ride!


Finding the right time to make the transition

Let’s face it, it’s never the right time. Knowing that the last paycheck won’t be coming in anymore is a hard pill to swallow. Here are my suggested goalposts:

  • Your job is literally killing you – stress leave seems like a dream that doesn’t go away and one you don’t want to take for fear of being stigmatized. It’s time to leave sooner than later.
  • You’ve saved up or have a cushion or other means of living for the first couple of years as a safeguard. You can afford a little time away from your regular income.
  • There’s a time-based decision regarding something in your personal or professional life that makes that timing decision quite clear. You’ve finished a work project; you need more flexibility at home; you’d love to have a lengthy break over the summer before hunkering down at work again…


Gradual transition vs sudden change pros and cons

Happy woman transitioning from employee to entrepreneurAka Turning your side hustle into your full hustle.

Research shows that the side-hustle is more popular than ever. In fact, one recent study showed more than half of Americans adopt side hustles with 54% of working Americans reporting taking on at least one opportunity for extra income in the past 12 months. Men were more likely than women to have taken on a side hustle, with 59% of men and 49% of women having done so.

The decision to make your side hustle your full hustle is dependent on your ability to self-fund yourself and the amount of risk you’re willing to take. How much money do you need? – like really need?

When I left my lucrative corporate career all those years ago, my husband was earning well, but my income paid for a lot of our expenses. We had to make financial decisions to change how we lived in favour of a better lifestyle for our young family. When dropping my daughter off at daycare (note: you still need childcare if you’re working!) a former colleague sighed and said they couldn’t afford for her to quit work – as she drove off in her brand new Range Rover and I pulled my 10 year old two-door Volkswagen out of the carpark. You make choices – and only you can make those. What’s more important? Are your choices from today fueling the future you want tomorrow?

Some financial realities

  • Have six months salary in the bank for you to live off of while you’re building your new venture.
  • Get a line of credit to help you through the ebbs and flows of irregular income.
  • It takes between 18 to 24 months for most new businesses to make a profit.
  • Almost 25 percent of businesses fail during the first year.

Parting note: find a mentor

You can’t do it alone. No one can. Enlist the wisdom of others who’ve been there. Surround yourself with people who believe in you. Network with entrepreneurs who are further along in their journey than you are. Know you can’t do it all and don’t expect to. With passion, courage, conviction and a plan to get there (including a financial plan – more on that in a future blog post!) you can make this happen. Starting your own business is a bold step towards creating a life that aligns with your personal values, goals, and aspirations. The future you’re looking for is within reach. 

Seeking further guidance? I’d love to support your transition and make those tough decisions while juggling all that life tosses your way. I designed EXPRESS specifically with you in mind to go from exhausted employee to empowered entrepreneur. Ready for your next big adventure?

To your success,

Susan Elford

Susan Elford is a Leadership Coach and Business Mentor who especially loves to work with women who want it all: a fulfilling career or business while living a full and satisfying life. Through powerful career coaching and business mentorship to get their career or business to the next level, Susan helps her clients get real about their strengths and celebrate and promote them so they get more of what they want: success at work; success in business & success in life.


Get clear about what’s right for you through a combination of questions, resources and empowerment with the Alignment Equation. Plus receive my biweekly newsletter designed for today’s busy woman to feel seen, understood, heard and prepare her for her next big step.

alignment equation image

Got a Career, a Business, a Busy Life...
and looking to get the most out of every day?

Join me on a journey to build a deeply satisfying life.

I share regular emails with my best articles, books I love, podcasts I enjoy, and ideas I'm sharing with my clients. Designed for the successful, creative, career and business-loving woman who wants it all... even at the same time.

You have Successfully Subscribed!

Free Training: Personal Balance Equation

Subscribe to receive this helpful free resource

You have Successfully Subscribed!

Free Workbook: How-To Guide to Get Your Business PR Ready

Free Workbook: How-To Guide to Get Your Business PR Ready


Subscribe to receive this helpful free resource


You have Successfully Subscribed!