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Is the Self-employed Life for Me? 6 Questions to Ask Before Taking the Leap

May 11, 2022

6 questions to ask before becoming self employed


Oh, the self-employed life.


For many, self-employment is the ultimate career goal. It’s a life where you can have much more control – from the type of stuff you work on, to the people you deal with.


Trust me, I know how enticing it can be. It’s why I took the jump myself and started my career as a freelance writer 2 years ago.


And it’s not just me – more and more people are joining the self-employed movement. One 2019 survey found the percentage of full-time freelancers in America has increased from 17% to 28% in just 5 years!


While being your own boss comes with an array of plus points, it also has its own challenges. Some of them can be pretty unpredictable.


Taking the leap of faith to be self-employed might not be the easiest thing to do but it’s not impossible – at least for most people.


Here are 6 questions you should be asking yourself before making the big jump to being fully self-employed.


1. What’s my why?


If you’ve started toying with the idea of becoming self-employed, then the first question you should ask yourself is why you want to do it.


Knowing the BIG WHY is crucial as it will be your biggest driving force to keep pushing in order to make it on this new path.


There are plenty of valid reasons to want to pursue self-employment—and, there are also some… err, not so sustainable ones.


The most common include:


  • Wanting to be your own boss
  • Working on meaningful and exciting projects
  • Taking full control of your own career
  • Creating something that you’re proud of


However, if you’re considering becoming self-employed just so you don’t have to be part of the mundane 9-5 rat race where work becomes a boring routine, or have unlimited vacation days, then you might want to rethink the leap.


Take it from someone who had these as her main reasons once, they never last!


woman with laptop and notebook on sheets

Working wherever you want? Yes please.


As such, take time to do some self-reflection and figure out what’s driving you to switch to self-employment.


If you look deep and hard, I’m sure you can spot valid and substantial reasons for making the jump.


In a nutshell

You should only move to becoming your own boss because you want to work towards something you love, and not to run away from something you hate.


2. What kind of self-employment do I want to do?


Now that you’ve figured out the why, it’s time to ask the what.


When it comes to selecting the kind of job that you want to do as a self-employed individual, the sky’s the limit, really.


You can do anything from setting up an online boutique or consultancy to becoming a freelance web developer or social media influencer.


However, I would say the key is to always follow your passion and strengths.


It’s also wise to come up with a business plan before you venture into the world of self-employment. Creating a business plan may sound like a lot of work but I can’t emphasise enough the importance of having it.


To put it in plain words, a business plan is your go-to reference book. If you feel stuck or lost at any point of your journey, then you can also look back at your own business plan to figure out what you should do next.


3. What are my financial commitments?


Let’s talk about the moolah now!


Being self-employed comes with a lot of uncertainty – you may not always know for sure who your next client is going to be or how much you’re going to earn in the coming month, or year. As such, it’s wise to lay out your monthly financial commitments before taking the leap.


Rent, insurance, grocery, utilities, Internet and petrol are some of the monthly commitments that most of us have, and it’s important to know how much money you need for all of them.


Before I opted to be a freelance writer, one important tip that I got from someone who succeeded in the self-employment world is to have a savings cushion.


Ideally, it’s best to have enough funds to sustain six months of your life. This is because there’s a high chances that you might not be making that much money when you first start and you’re building your portfolio.


But fret not – with luck as you build your portfolio and experience, so it will be easier to find clients and pick up your business. To be on the safe side, prepare a financial buffer to weather any lulls at work.


4. Am I up for a challenge?


“It must be so great to work whenever you want!”


This is something that I’ve repeatedly heard from almost everyone who knows I freelance for a living.


My typical response would be to remind them that while it’s nice but, it also means that I put in the extra hours to get the job done all by myself with no help from other colleagues. Some days I work 18 hours a day, which is double the hours of a regular office job!


child standing before bottom of stairs

Are you ready to work for it?


To put it plainly: being self-employed is hard work. You’re a one-person show, which means not only do you have to take care of all the tasks and to-dos yourself, but you also have to learn new skills that you may have never known you needed, like bookkeeping.


But the good news is that no one day is the same!


Self-employment isn’t all about freedom and flexibility. You have got to be prepared to be extremely disciplined about work and go the extra mile to get things — ahem, everything — done.


5. Do I have a solid support system?


Embarking on the journey of self-employment is definitely an exciting one. However, there will be times when you can feel demotivated, lost or uninspired, and this can affect your work.


When such feelings strike, it’s best to talk to someone or seek advice from a person who you trust and is comfortable with. There’s no shame in asking for assistance, really!


Talk to a friend, sibling, parents, former boss, or anyone who you think might be able to help you solve your issues.


Self-employment can be hard and lonely at times. External sources of support can help you feel less overwhelmed and more positive about your endeavours.


But, if you don’t have such individuals in your life, then you know what they say – be your own cheerleader!


Alternatively, you can also sign-up for online support groups where you can get to know like-minded individuals from the same industry. For a start, try joining freelancer/entrepreneur groups on Facebook or look for different groups on Slack, Discord or Reddit.


While you’re there, you might even find yourself a mentor, someone who has accomplished what you’re trying to do and can provide valuable insight and guidance.


6. Do I have a Plan B?


The first step to becoming self-employed is to make the decision to do so. Like anything new in life, the toughest part is usually the beginning.


When you first step foot onto this new path, you will have to learn everything from scratch – from working out a schedule that suits you to planning finances and setting up a business model. And with time and experience, you will slowly get the hang of it – I certainly did!


However, sometimes, things just don’t go according to plan. You might struggle to secure clients no matter how hard you try, or perhaps a better full-time opportunity comes knocking.


If things are not working and you’re starting to lose motivation and hope, you’ll need to make the decision if you want to carry on with self-employment. Here are 2 approaches you may want to try:


Give yourself a deadline


My suggestion here is to give yourself a certain amount of time to go-all out on this path, before calling it quits.


For instance, you can give yourself a year to start something of your own, and then re-evaluate how your business is going after that given time period.


If you think you are not making enough cash flow to sustain the business, or you can’t seem to retain your clients for the long-haul, then perhaps you want to think deeper about self-employment.


Take it part-time instead


Instead of becoming a full-time freelancer, this could be the best time to transition into freelancing on a part-time basis so you can build your clientele or upgrade your skills.


By doing so, hopefully you can one day get back into the world of self-employment again.


Wrap Up


In conclusion, all I want to say is that the boss life is hard — no surprise there — but it’s definitely worth it.


Self-employment is not for everyone. If you’re able to answer yes to most of the above questions – congrats! You’re on a strong footing to go ahead and kick off your self-employed life.


That said – if you want it enough, and you put your mind to it, you can accomplish anything.


Good luck!



Rubaa Shunmuganathan

About The Author

Rubaa's an experienced writer who’s written for publications on everything from property and food to travel and culture. Besides her love for words, she’s fond of baking, testing out new recipes and forcing her family and friends to try them. Get in touch with her via LinkedIn.