7 Reasons People Struggle to Succeed at Self-Employment

For decades cartoonist Walt Kelly had a very popular comic strip that starred Pogo, an opossum. Pogo had an oft-quoted line, which was this: “We have met the enemy, and he is us.”

That statement encapsulates the fact that all too often, it is our own behaviors that will get us in trouble or that slow us down, including when we’re seeking to succeed as our own boss. I’m going to talk about behaviors, attitudes, or habits that you should strive to avoid if you hope to thrive at self-employment.

In my nearly 30 years of self-employment, I’ve seen both clients and colleagues sabotage their success by falling into these behavior and attitude traps.

If you want to achieve all that you’re truly capable of achieving and live your dream of self-employment success to its fullest, here are seven pitfalls you should avoid.

Pitfall #1: Analysis Paralysis

Analysis paralysis is a problem for many, many people. When you’re stuck in this behavior pattern, you put off decision making until you have every last bit of information in your hands. This is an extremely common phenomenon throughout the business world . . . and beyond, of course.

I’ve witnessed this inability to pull the trigger on decisions both large and trivial in a timely way everywhere from large corporations to one-person businesses.

For someone who is self-employed, analysis paralysis can bring your forward momentum to a grinding halt. The longer you spend gathering every last snippet of data before deciding how to move forward with your marketing or whatever it is you’re dithering about, the longer you will spend spinning your wheels in the status quo.

Here are three ideas to consider when you find yourself unable to make a move because you’re suffering from analysis paralysis:

First, not deciding is deciding. I’m a pretty decisive person, but there are times when I just can’t make a choice. Then, I remind myself that by delaying, I actually am making a choice . . . a choice not to move ahead.

The longer you wait, the greater chance there is that the window of opportunity you originally saw will close up as competitors who are more nimble decision-makers move ahead. There may be a cost in delaying, and in some cases, it can be considerable.

Second, when you’re self-employed, no one’s opinion counts more than yours. I have had clients who have kept saying, “I just want to have one more person look at this before I decide.” And then when that one more person has looked at it, they suddenly remember yet another person whose opinion they must have before moving ahead.

I’m not saying you shouldn’t check with trusted advisers. But if 10 people have told you it’s a good idea— or a lousy idea—should that 11th person’s opinion really make all the difference in what you decide?

Third, learn to trust your gut. When the research you’ve done conflicts and the people around you are divided over an issue, it’s sometimes necessary to go with your intuition. It won’t always be right, but if you have solid experience and have done a reasonable amount of research, you’re probably not going to drive your business off a cliff by deciding to go with your gut on something.

To build faith in your intuition, try to make note of the many small and correct decisions you constantly make based on nothing more than your instincts. This will give you faith that you can do the same when it comes to making bigger, more impactful choices.

Pitfall #2: Frequent Second-Guessing

Closely linked with analysis paralysis and the insecurity that causes it is frequent second guess. My last boss made a habit of rethinking decisions that the rest of us on the management team thought had already been settled. Man, does that get tiresome fast!

Second-guessing decisions and frequently backtracking or switching directions can be highly detrimental and negatively affects how those around you view you and your judgment.

Your constant second-guessing can drive other people nuts. Subcontractors and vendors – and any employees you might eventually have — may never totally commit to a strategy because they know it might be abandoned shortly.

When changes in direction are frequent, nothing new ever gets fully embraced because your colleagues think it’s unlikely to last. They’ll think you’ll come up with a new plan next week. And clients become confused when you announce one month that you’re offering a new service, for example, only to decide two months later that you’re moving in another direction instead.

Strategies and plans with real potential are never given a full chance to succeed.

If the slightest resistance is felt or things don’t go 100 percent according to plan right out of the gate, everything gets tossed overboard and it’s back to the drawing board. This ignores the fact that very few things ever go perfectly.

Success is never guaranteed, but good ideas that have been thoroughly researched and planned are worth giving time to prove themselves. Sure, tweaking needs to be done more often than not, but that’s far different from second-guessing yourself and abandoning something before it’s been given a real chance to make an impact.

The root of such indecision, of course, is self-doubt. The next time you feel the urge to revisit a decision, stop and think about the impact this bad habit might have on your business if you’re self-employed. Will clients or customers be confused by your sudden stops and starts?

So before you do any second-guessing, consider if you really need to revisit a decision, or do you just need to tweak things a little bit?

Are the reasons you made the decision in the first place still valid? Did you make the decision based on good input from subcontractors, customers, mentors, and business advisers? Has something really changed that makes the decision suddenly invalid, or are you just feeling insecure because things aren’t going absolutely according to plan?

Have you given the decision enough time to work, or are you in danger of pulling the plug prematurely on what is still an essentially good idea? Consider these questions carefully before changing directions yet again.

Pitfall #3: Failing to Update Your Skills Updated

When you’re self-employed, allowing your skills to become outdated can put you at a severe competitive disadvantage. Several reasons make it easy to just keep delaying getting up to speed on new developments in your field if you’re out on your own.

First, when you are self-employed, any training you get is at your own expense and on your own time.

Nobody is going to pay your fees and travel expenses if you want to go to an industry conference or meeting. When new technology comes along that you need to master, that definitely can be time-consuming and, in some cases, may even involve adding a new expense to your monthly costs.

Secondly, any time you take for training cuts into the time you have to do client work and thereby generate income.

Given the choice between spending an hour on billable work and spending that same hour participating in a training webinar, many self-employed people will opt for the income and ignore the risk posed by having out-of-date skills.

Self-employed people who don’t invest time and money in keeping up-to- date are focusing on the short term and ignoring the dire long-term consequences of not staying current with developments in their field. I know it’s sometimes tough to add one more thing to an already busy schedule, especially when you might not see an immediate payback. But take this approach for too long and clients and prospective clients will begin to notice.

Sure, if necessary, you can always outsource portions of projects that involve skills you have not yet mastered. But this involves sharing part of your income with someone else, which isn’t something you really want to do over the long haul, especially if it involves skills that are becoming integral to your profession. Regularly devoting time to professional learning makes much more sense and will help ensure that you maintain that competitive edge.

Pitfall #4: Trying to Be All Things to All People

When you’re first getting your business off the ground or any time you experience a cash flow ebb, it is tempting to jump at any project, even if it’s something you’re not an expert in or even enjoy doing. This trying to be all things to all people might bring in your initial clients or solve short-term cash flow problems, but in the long run, it can get you in trouble.

In an ideal world, you perform work that you’re highly qualified to do, and therefore, you’re doing a fabulous job for everyone. Also, you love what you do, and this shows in the results.

Contrast this with what happens when you take on a project that isn’t really your thing. Maybe it doesn’t match your key skills or you don’t have a lot of experience in it. But you’ve managed to sell yourself to the client anyway, chiefly because they don’t know enough about what the job requires to understand why your experience isn’t a good fit. Or perhaps it’s something you are qualified to do but hate doing.

In the vast majority of such cases like this, problems ensue. Maybe you do an okay but not great job. But okay doesn’t cut it in today’s competitive environment. The client is disappointed and decides not to hire you again, even for projects for which you are eminently well qualified. Worse yet, they may bad-mouth you to others.

Make it a practice never to mislead clients about the extent of your skills and experience. Know what your strengths are, as well as your weaknesses.

Always remember that the client’s interests should remain uppermost in your mind. Sure, it may be possible to make a quick buck from someone who doesn’t know the right questions to ask you to determine your qualifications, and you may even end up doing a half-decent job. But then again, you may very well bite off more than you can chew if you tackle a project for which you’re not really prepared. Your reputation will invariably suffer if you stray too far from your strengths.

Build your skills the right way, not at a client’s expense. If you want to get experience in a new area, first read as much as you can or take a course or two to get up to speed. Once you have a good grasp of the subject, consider partnering on a project with someone who knows that field really well. This will ensure that the client gets a good product, you’ll start gaining the hands-on experience you need, and everyone will be happy.

Pitfall #5: Perfectionism

Okay, I can already hear some readers mumbling, “What’s wrong with being a perfectionist? I’m proud to be a perfectionist!” Well, there’s plenty wrong with it.

When you can’t let go of something until it’s perfect, you’ll procrastinate, perhaps face cost overruns, and may not satisfy your boss or your client because you’re so late with your delivery. What good is something to a client if it is perfect but gets there too late to be of help or actually causes problems with the firm’s own operations?

In general, clients don’t like vendors—no matter how great their work is—who cause them heart palpitations by constantly pushing up against, or even past, deadlines.

Related: Why Done Is Better Than Perfect?

There’s also another problem with perfectionism. If you’re fussing over every single detail of a project, you will tend to make things more complicated than they need to be. Perfectionists overanalyze, overthink, and, in general, overdo everything. They tend to lose sight of the big picture. And perfectionists are never really satisfied with anything, which can make work very unrewarding.

If you have employees, your perfectionism will drive them nuts as you try to micromanage every aspect of their work. It can be especially damaging if you have senior people with considerable experience who don’t really need or want you looking over their shoulder constantly.

Another downside of perfectionism is that you may end up working hours for which you will not be paid.

If you have given a client a fixed budget for a project but continue to work beyond the hours that budget calls for to achieve that elusive “perfection,” you will, in essence, be working for free during those extra hours. For this reason, make sure you’re tracking your hours carefully. If you see that you’re in danger of putting in time for which you will not be paid, this signals that either you didn’t set the budget correctly or, more likely, your perfectionism is getting in your way.

This is not to say that sometimes running a little over budget is not justifiable; that happens to all of us from time to time. But if you do this constantly, take a good look in the mirror and see if you’re not looking at someone who needs to dial back on being a perfectionist.

Even if you don’t have a budget cap and can bill every hour you work, this may end up with a final total cost that is not pleasing to the client. Next time they have a similar project, they may look for a more affordable solution. In other words, your perfectionism may price you out of the market.

Obviously, I am not arguing in favor of being slipshod. We all take pride in our work and want to do a good job for those who buy our products or services. But there does come a point in every project where the law of diminishing returns kicks in and you need to recognize when the amount of difference you’re making by seeking perfection simply won’t be meaningful enough to your end-user to justify the effort.

Pitfall #6: Clinging to Your Comfort Zone

A few years ago, I had a conversation with a friend about a potential project I was hoping to pass along to her. She told me she had thought about the assignment, which was ghostwriting a book, and decided it was “outside her comfort zone.”

Now, she had several valid reasons for not wanting to take on a new project right then, including an imminent move to a new home. But not being willing to step outside her comfort zone to try something new that would significantly expand the potential of her business seems to me to be an all too common mistake among many self-employed people and small business owners.

This was only one of many instances I’ve seen of friends and colleagues who were not willing to try something new. They cling to what they know, even when what they know isn’t working that great for them. They’re certain that if they just keep beating that dead horse long enough, things will turn around. Or, if things are going okay, they still hesitate to try something that may make things even better.

They stay in their comfort zone, unwilling to take a risk, even if a risk/reward analysis would show them that the risk is relatively little and the potential reward is significant.

My question to you is this: Do you want to spend the rest of your career inside your comfort zone without ever finding out just what you might achieve if you stretched yourself a little?

I realize everyone has different levels of risk tolerance based on the financial demands of their lives. And if you’re totally happy and your financial needs are being met by staying within your current comfort zone, then you may have little motivation to try something new and different. But if you do step outside that zone and succeed, you will find that great satisfaction comes from conquering your fears and expanding your comfort zone.

What I wanted to say to friend back then was that your comfort zone is not a static thing. It can change and grow, and as it grows, so do you. So the next time you find yourself turning down an opportunity because it is outside your comfort zone, first carefully consider whether your comfort zone isn’t really more of a trap than something that brings you comfort. Don’t handcuff yourself by turning your back on opportunities.

Pitfall #7: Impatience

In an era in which we frequently read about college dropouts who start tech companies and become millionaires (at least on paper) within months, it is difficult—yet critically important—to remember that this is not the way most careers happen.

One of the worst mistakes you can make as you launch your career or start your business is to become impatient.

One cause of such impatience early on may be that you started with unrealistic expectations. If you’re launching a business and didn’t do adequate research you may not understand how long and how hard it can be to build the thriving, growing business of your dreams. If you’re starting on a career path as an employee, you also may not completely understand how long it will take you to work your way up to the job of your dreams.

If you’re running your own business, remember the rule of three – it always takes three times longer, three times as much money, and is three times harder than you thought? I don’t think that’s too far off the mark for many businesses. I think the 3 times longer part of that is particularly true.

Here again is where having mentors can be a big help. People who have run their own businesses and/or have advised other people taking a similar career path as you are know the wisdom of the old adage that “Rome wasn’t built in a day.”

They can help temper your impatience and make you realize that what you’re experiencing is what the vast majority of people who are new to self-employment go through in terms of things not happening as fast as they’d wish.

To go back to Pogo’s line – “We have met the enemy, and he is us” – it’s a good idea to periodically take a hard look in the mirror and make sure you’re aren’t falling into any of the traps discussed here.

Having an honest self-check several times a year can mean the difference between going blindly ahead and ignoring behavior and attitudes that can imperil your success and recognizing what you need to change to achieve all your self-employment goals.