How to know whether or not self-employment is right for you
To be or not to be an entrepreneur? That is the question.
Many people feel they are destined for entrepreneurship.
You know those stories that start with ‘I always knew I wanted to be my own boss”?
I’m definitely guilty of that one!
But as the world becomes more and more entrepreneurial, it seems more people than ever before are self-selecting to start businesses.
Was that always their path?
Or has the barrier to starting a business become so easy, that for many, they are pursuing self employment when they might have been better suited to traditional employment after all?
My big mission in building The Ask, is to guide and educate ambitious and entrepreneurial professionals like you to find your place in the world of work. Specifically, how you can decide, plan and build the right career path or business idea for you.
In which case, it might be considered that I believe those who are the ‘right fit’ for entrepreneurship, would naturally find their way to it.
We know this is rarely the case, however, as many people stumble into it accidentally, or sit on the side lines for years, never taking the leap (when they should have a long time ago!).
This post poses four key questions to help you consider if in fact self-employment is right for you at this point in time, and offers some real-life perspectives of those who already made the leap.
Becoming self-employed (or not) is rarely a binary choice.
Many people will find entrepreneurship to only later leave it behind.
Many will exist happily as both an employee in someone else’s business whilst doing something of their own at the same time, too.
You’d think that if being an entrepreneur was like gaining entry to some kind of membership club, my role as a career change coach would equate me to a bouncer. Ushering people through, determining whose in and who’s out
Whilst that would indeed be a cool job, I see my role instead as helping people to make the right choice for them at that given point in time.
For me, I was a lot younger than some entrepreneurs (and coaches) when starting out, and have likely had to contend with those stereotypes and challenges, compared to someone with more life and career experience becoming a career and business coach would have.
Aside from that, the stars kind of aligned for me to become self-employed when I did in late 2019.
The unique circumstances being the concoction of factors relating to money, time and relationships in 2019. Plus as I wrote about here, the big driver I had to seek out maximum career fulfilment (which I felt only self-employment could provide).
And for you?
As you go through these four questions I encouraged to feel your way through the scenarios and see what comes up for you — does it seem worth it, on balance?
Know that your answer to that question may well be different at another point in the future.
I’ve quoted some founders I asked this question to, from the Found & Flourish community I’m part of — an incredible support network for fellow female entrepreneurs I highly recommend.
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1. How do you feel about Money?
The first question being; how do you feel about money, and the role it plays in your life (and the impact being self-employed would have on it)?
Sure, it would be great if we could guarantee more money by working for ourselves… but for many people that isn’t the reality, at least not at first. Employment offers predictable income, and how you feel about that ending is very important.
‘Feast or famine’ is something entrepreneurs often describe when it comes to managing their finances, because sometimes it can really feel like its flowing and other times… the tap is dripping at best.
So think about your relationship with money and if you’re okay for it to become more uncertain.
Then consider what you have coming up in terms of financial requirements — mortgage application? Easier if you’re employed. Big wedding? You may need the secure savings.
This is so personal to answer, because your monthly income might not be the most important factor right now, anyway. Perhaps you have a lot of money saved up, or the support of a partner or family member, or generally live in a life with low financial overheads. These things make earning less money short-term, more palatable.
Only you can say how much the money factor plays a role in your decision to become self-employed or not — but one more thing — if you go ahead, be prepared to spend money ON your business, not just get money FROM it.
You will encounter many expenses starting out, and investing in yourself and your business’ growth, is a pretty solid insurance policy.
Better than the stock market if you ask me.
Here’s what some fellow founders had to say about the money aspect of becoming their own boss.
“Regarding money, slow down, take your time and really feel into what you want to do and offer. It's taken me a long time to get to Project Woman because of my own emotional instabilities. When you find your sweet spot, investing in it becomes easier and your focus becomes sharper”
— Abi Adams, Female Health & Emotional Coach.
“I wish I'd learnt the basics about financial management early on and really taken responsibility for this side of my business from the word go, it's only recently that I'm beginning to see how much I let the money side of things just 'happen' to me, rather than be in control of them.”
— Rebecca Mackay Miller, Founder, Bloc + Rose
“I wish I'd have known that I would get triggered often by money and the conditioning we have to salaries in society. The feast or famine aspect to self-employment took me ages to get my head around and finding solutions to this was something I wish I'd have known from the start. Now I am much more measured, organised and don't relate my income to my self-worth, but personal value is now in terms of how many people have I helped and what is the ripple effect of what they can now do. Supporting others during covid taught me that health was the greatest asset of all. Everyone wanted to be healthy - money mattered less! Once I stopped obsessing about money it flowed more!
— Jo Permaul, Director , Wellness Professionals At Work.
2. How do you value your Time?
How do you feel about the amount of time you give to your work? (She writes on the 11th hour working, two days in a row…).
Not to glamourise working around the clock, it is just that you’ll be hard pressed to find many entrepreneurs who don’t work long hours on a pretty consistent basis.
As the saying goes:
“I don’t have a 9-5 I have a 24/7”
However, whilst you may end up working more hours, you’ll likely find that you get a great deal of flexibility around when those hours occur. No one can tell you off for lying in or leaving to pick up your kids up from school, or taking a mid-day siesta and Netflix marathon on a Wednesday.
You get to choose.
You just might then end up working on Saturday, and skipping that friends’ birthday.
Importantly, the number of hours that you work does not directly correlate with your output.
So how do you show up to those hours?
Are you good at getting things done, staying focused, and wading through your to-do list? It will be on you and you alone, to use this time effectively.
Here’s what other founders said about the time aspect of becoming their own boss.
“I wish I’d known myself a bit better! I’ve discovered I’m not a naturally disciplined person, even though I used to thrive in jobs and workplaces. Making the transition to being self-employed was tough for those first few months as I had so much freedom, too much freedom, to spend my days how I wanted! I have a good balance now, but it takes work - every single day!”
— Molly Gould, Founder of brand storytelling business, Effable.
“A good friend recently told me ‘swap the word time ‘time’ with the word ‘life’” I realised I don't want to waste my life on things that no longer serve me. I’d rather make an effort with the things that I love. During COVID I realised I didn't really know what I loved! It had all been boxed away and hidden. Me and my family moved to Devon in 2021 as I got a calling to say that if I didn't leave London I was going to become very ill (I believe this was the onset of perimenopause). I'm so pleased I listened as I realised just how much time/life I was wasting.”
— Abi Adams.
3. How do you feel about other People?
How much do other people play a role in this self-employed v employed conundrum for you?
Either, the people you are choosing avoid working with by pursuing self-employment — bosses, coworkers etc — or people you are choosing to work with, by pursuing it.
When your team, clients, and services providers, mentors and coaches are people you would willingly spend time with and learn from… life begins to get pretty fun (even during those long working hours).
You would also want to consider the impact of self employment on those closest to you.
How will it impact your relationships. Will you get their support? Will they understand that your priorities might shift, and you might have less time for them? Honest conversations are key.
Here’s what other founders said about the people aspect of self-employment:
“I wish I had known the extent of the sacrifice I'd be making both in my personal life and relationships to run a business. The late nights, the missed social events, the weekends working while your family do fun things together. It's a lot. I’d have the conversations as early on as possible with the ones you love about what you are about to embark on and the sacrifice you'll be making in order to make your endeavours a success. Entrepreneurship is a ride, there are lots of highs but also many lows so your support network will be key. Find a community who are on a similar journey as you, because sometimes the ones closest to you just won’t get it. Ultimately though I found a sense of peace when I realised I will never get it all done, there will always be more to do. So, take that walk with your partner, go to that party with your friends, read that book to your child, because if time has taught us anything, it’s that these moments are worth protecting.”
— Lara Sheldrake, Founder of Found & Flourish
“Becoming a Wellness Coach and Homeopath was the most enlightening journey ever. However I was constantly rubbing up against the structures my family and friends operated in and at times would miss events, have my viewpoints challenged and feel like I was talking a different language! But I wouldn't change it for a single thing, and now my kids are 17 and 20 I feel like I have this wonderful evergreen project to work on that fills my soul up daily, whereas many women in salaried jobs are becoming frazzled, disillusioned and envy my flexibility!”
— Jo Permaul ****
4. How do you feel about Fulfilment?
Within ‘fulfilment’ comes the levels of creativity, growth and satisfaction you get from your work.
How you feel whilst doing the work itself, and how much importance you place on feeling fulfilled within your work day-day, in general.
Self-employment is not a panacea for fulfilment and there will certainly be days when you don’t enjoy doing your job or its inherent responsibilities. Wearing all the hats, some will naturally suit you better than others.
However, given that you are writing your own job description, overall hopefully your responsibilities are more fulfilling than they would be in an employment capacity where you have less say over what you work on each day.
From my side, I love nothing more than reading and thinking about ideas which I can apply to coaching or content creation. That is uniquely fulfilling to me — which is why I designed my business model around these activities.
Consider how much the life of an employee vs business owner would impact your feelings of fulfilment and how important this factor is for you.
Our female founders share their perspectives of how they feel about their work:
“Working for myself allows me to tune into my creative pockets of greatness when they naturally arise (menstrual cycle syncing has been my greatest gift to myself as well as the women I work with). I could never do that when I was working for someone else, mainly because what I was doing wasn't setting me on fire and was making me miserable, so the creative juices were put out with alcohol and shitty relationships instead. A woman's cycle just isn't as supported in the corporate world, and that's why I believe it's so important to include that in your success strategy”
— Abi Adams
“I think being self-employed has allowed me to fully be myself, to push up against some joyous moments and hugely uncomfortable edges, allowing me to embrace both my strengths and my shadow all at once”
— Jo Permaul
A big thank you to these founder’s perspectives, and I hope they can all shed light on your own decision making around choosing self-employment, or not.
If you have made the leap already, are you giving yourself the support you need when it comes to time, money, relationships and fulfilment?
The most ambitious professionals I know view themselves as core to their businesses’ success, and see working on themselves as part of the process, like personal product development. There are so many pieces to the puzzle of a successful entrepreneurial career; balancing how you work as well as how you show up to the work.
I love supporting people to make these trade offs, balance working on their own projects as well as paid employment at the same time (if they so wish) or going all in on their own businesses. This decision making and analysis can be worked through in coaching if you are feeling unclear, I offer free coaching consultations for this reason.
