The Self-Employment Mindset

Can everyone succeed at self-employment? This question comes up every time I speak to an audience about my new book, The Self-Employment Survival Guide: Proven Strategies to Succeed as Your Own Boss. Being asked this question repeatedly has prompted me to think about the mental mindset that is required for self-employment success.

Based on nearly 30 years of being my own boss and from close observation of self-employed clients and colleagues, here are five attributes that are part of the mindset that will help you succeed out on your own.

The good news is that if you’re not strong in most of these, ways exist for you to build yourself up and become stronger.

Persistence

When you’re self-employed, you often hear some version of “Thanks, but we’re not interested.” But you must persist. When one new business opportunity falls through, you must get right back in there and seek the next opportunity.

Persistence is also important at other times, like when a client’s payment is overdue. You have to persist in reminding them that they owe you money. If you are someone who will shy away from asking for what you’ve earned, self-employment can be quite difficult.

You might need to look into assertiveness or communications training that will help you become more comfortable in doing things. Things like negotiating good deals and dunning clients when necessary.

Decisiveness

Until you’re self-employed, this is probably the first time in your entire career where you have the ultimate decision-making power. Previously, a boss set your priorities and decided how you’d spend your time. That changes dramatically when you become self-employed. Now you are responsible for every single choice that needs to be made about your business.

You need to be able to make decisions in a timely manner and then stick with them. Every day is filled with choices about the direction you’re taking your business, what you need to do next to move your business forward, and about the work you’re doing for your clients.

Making this transition to being the decision-maker can be smoothed if you understand your decision-making style. Are you someone who has to research everything to death? If so, you probably need to lighten up a little bit on that or else decisions will never get made. Also, it helps to have a friendly sounding board for when you’re making a really big decision.

A friend who is also self-employed can often provide objective feedback on the choices before you. Finally, learn to trust your intuition; it will usually guide you right.

Risk tolerance

The list of potential hazards you may face when self-employed is long and daunting. Everyone who is self-employed has cash flow worries and has to chase clients for overdue money now and then.

We all worry about juggling the competing demands from clients to keep everyone happy and satisfied. We all have clients who don’t meet their own commitments, causing projects to fall behind, so we have to work nights and weekends to make up for their laxity. We all are at risk of losing clients for external reasons, having nothing to do with the quality of the work we deliver.

If you aren’t risk tolerant, you may find yourself frozen in place, unable to set priorities, make decisions, and take necessary actions.

Now, the good news is that with experience, you will learn how to overcome many of the risks you face. For example, as I advise in my book, you’ll learn to ask for deposits before starting work for new clients so that if they turn out to be slow payers, your cash flow won’t be quite so compromised. And as you succeed at facing and conquering more perils that come your way, you will gain confidence in your ability to stay the course and succeed.

So risk tolerance is something you can build over time and that’s good news for anyone considering self-employment.

Optimism

I won’t say that a pessimist can’t succeed at self-employment, but I definitely think it is easier to succeed if you’re an optimist by nature. People are attracted to people who have a positive attitude and an optimistic outlook. It’s hard to convince yourself to do business with someone who always thinks the sky is falling. Also, in my experience, I’ve found that pessimists worry too much about things that are never going to happen. This is energy they could be using to move their business forward.

If you’re a pessimist, you’ll also have a harder time recovering from the inevitable blows that come your way when you’re self-employed. Each time you lose a customer, for instance, you’ll take it harder than someone who is optimistic and works off the philosophy that when one door closes, another one will open up.

Self-motivation

Finally, let’s talk about self-motivation. A comment I’ve often heard over the years when I tell people I am self-employed is this: “Oh, good for you…I don’t think I have enough self-motivation to be self-employed. I’m not sure I could stay on track.” My response has always been that the thing that motivated me most was the mortgage bill arriving in the mail every month…that will motivate almost anyone!

Yes, it is important to really like what you’re doing, but most reasonably well-adjusted people will find within themselves the motivation to do what needs to be done in order to pay the bills.

If you truly feel you need external motivation – that you need a boss to hold you accountable for getting things done – then self-employment probably is not for you. But I doubt that is the case for the vast majority of people, especially those with plenty of work experience under their belt who are looking forward to a career change.

This was written by Jeanne Yocum. Jeanne has nearly 30 years of self-employment experience and is author of The Self-Employment Survival Guide: Proven Strategies to Succeed as Your Own Boss, which is available on Amazon and in bookstores nationwide. Her blog is SucceedingInSmallBusiness.com.

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