When I quit my job, on the cusp of a landmark birthday (MYOB), I said to myself and others, “If I’m going to work this hard, I’m going to work for myself!”
My work ethic is pretty simple: “Tell me what you want done and I’ll get it done, no supervision required. I don’t care how long it takes me, it will be done on deadline and it will be right.”
I’m organized, motivated, efficient, creative and have high standards. With that skill set, I figured the transition into self-employment would be easy.
Little did I realize that hard work was just the beginning. And some of the very things that made me a valued and valuable employee came back to bite me when I started my own business.
Here are some of the biggest challenges of being self-employed that I’ve faced and the things I’ve learned (with the help of my friends and clients) in the 16 months I’ve been self-employed.
- When you roll out of bed every morning, you have to ask yourself, “What am I going to kill today to put on the table?” Sounds very primitive, doesn’t it? But it is a cold, hard fact: You have to be looking for work – “farming,” as my Realtor clients put it – every day. Today’s client might not be there tomorrow. Who will replace that person when they leave?

- “When someone is paying you for a Pinto, you don’t give them a Cadillac.” I posted this one day on Facebook and you would have thought I’d endorsed human sacrifice.
Nevertheless, it’s true. If you are being paid by the project, the longer you take to get it done, the less money you make. And if you are being paid by the hour, you want to provide a quality product or service without leading your client into bankruptcy. There’s a happy medium, and only you can figure out what it is.
- Don’t undervalue yourself. People starting out in business (especially women, I’ve found) have a tendency to think that their time or knowledge or skills aren’t worth much.
Part of what you’re worth is determined by the market, what other people are being paid and what people can afford.
But understand that people will pay more to get exactly what they want. Think of your own spending. Are there products or services that you buy at a higher price because nothing else compares? I know I do.
There’s more involved than money, right? It’s about reliability, service, honesty, friendliness, trustworthiness and a host of other qualities that might not be so easy to measure. So don’t cheapen what you do, and be prepared to explain those intangibles that make you worth every penny. If you don’t value yourself and what you do, your prospects won’t either.
- Manage client expectations. Let your clients know what to expect. “For X, you’ll get Y.” Be very specific. In writing. Signed by both parties. It’s not about trust, it’s about clarity. You don’t want misunderstandings down the road that could lead to ugly confrontations, bad feelings and – horrors! – awful online reviews of your work.
- Be honest. It sounds like another “well, duh” conclusion, but never, ever forget it. If your client asks you for something you’ve never done before, tell him that (a) you can do it, but it’s going to take you longer due to the learning curve or (b) suggest another person or company that specializes in that type of work.
You might end up turning away work that would put food on your table, but you’ve gained enormous goodwill in the process. Chances are excellent the word will get around, bringing new prospects or even the guy you originally referred to someone else.
- Plan your work and work your plan. Every day – many times during the day – ask yourself: “What’s the most important thing I can be doing right now?” Focus on what will bring the greatest returns.
- Set aside time to work ON your business, not IN your business. Block off time every day to do the things you need to do. It might be bookkeeping or paying taxes or farming for new clients or scheduling social media posts or updating your website. When you become more successful, and can afford it, concentrate on those things only you can do and outsource the rest.
- “It’s not what you do, it’s what you know that’s important.” For example, if you build websites for a living, you will always be limited to the number of websites you can realistically build in a week. Find someone who is faster, better and less expensive than you to do the rote work. That will allow you to move down other income-generating paths while the work still gets done.
- Don’t expect overnight success. Nearly half of small businesses fail within the first three years for a variety of reasons (click here for details). But don’t let that kill your dream. Just be smart about it.
Working for yourself is exhausting and time-consuming, as well as richly rewarding because you are working for you, not someone else. Your success is directly attributable to the things you do and learn, not dictated by someone else’s company policy. Are you self-employed? Please share your experiences here. I’d love to hear some other tips!