Self-Employment: A Reality Check
Self-Employment: A Reality Check

self-employment starts as a dream but can become a realitySelf-employment is becoming more and more common, as shifts in the economy make some jobs obsolete, and new technology makes self-employment easier than ever before.

Who hasn’t had the conversation about their dream business? Whether your dream is to open a fly-fishing shop, a cupcake café, or offer virtual assistant services from a home office, you should spend some time on research and planning before your business goes live. Maybe buying a franchise makes more sense for you as an alternative to starting something from scratch.

Once you’ve considered some of the important preliminaries — what you want to do and what you’d be good at — it’s important that you take a sober look at your strengths and weaknesses and confirm you’re right for entrepreneurship. I often tell clients, “just because you can do something doesn’t mean that you should do it.”

It’s important to be realistic about your strengths and weaknesses. When you’re out on your own, your personality traits, strengths and weaknesses will be magnified. You’ll need to find ways to consistently compensate for your weaknesses and make great use of your strengths. This is something that I always address when working with career coaching clients who are contemplating a career change of any kind.

Are you resourceful and resilient? To be in business, you need to be both. If you have trouble saying no, this is going to cause you real problems when it comes to dealing with customers. If you’re not naturally organized, you can find yourself in real trouble at tax time.

self-employment often takes a lot of work to get establishedAre you able to supervise and manage staff? If you find you need help in your business, are you going to be comfortable being in charge of people? Friends and family may cheer you on or they may tell you that you’re out of your mind to want to leave your secure job. Either way, some strategic advice can help you bounce ideas around in a constructive, objective way.

Don’t Rush In

Ideally, you’ll have a chance to plan things out and do some thorough research while you still have a steady paycheque. If you can, ease into your business and learn as you go, with what’s being called a “side hustle” these days.

Do your due diligence. Research, research, research. Get out and talk to entrepreneurs. Go to business networking meetings. Find out what it’s really like to be your own boss. For example, if you’ve been an employee for some years, you’ve probably never approached a lender to ask for a small business loan. When ‘Jane Smith’ (a former client) left the federal government to open her own clothing shop, she says she experienced a “rude awakening.”

For one thing, once she wasn’t a civil servant, the credit union that held her mortgage was a lot less friendly. “Once I became self-employed, they had very little time for me. I couldn’t get a small business loan or line of credit because my business was too new. I couldn’t even get overdraft for my business account.”

self-employment is possible if you're prepared to work for it


As for the “freedom” aspect of being your own boss?  Jane learned the hard way that self-employment shouldn’t be confused with freedom. “I was going to set my own hours and do things my way. It turned out I worked longer hours than I ever did before, and I had more bosses than ever. Your customers become your bosses. I ended up with hundreds of bosses to please.”



If you’re curious about whether self-employment is right for you or you’re not sure where to start, I invite you to contact me by email, or book a free 15 to 20-minute phone call. If you prefer messaging via social media, then send me a direct message on Twitter, Facebook, or LinkedIn.


More than career coaching, it’s career psychology®.


I/O Advisory Services – Building Resilient Careers and Organizations.™


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