One of the most frequent questions I’m asked when people learn I’ve written a book about my nearly 30 years of experience with self-employment is “What does it take to succeed as your own boss?”
Often, what they’re really wondering is whether they have what it takes to make it out on their own, which is a dream for many, many people. Another way people pose this question is this: “Do you think everyone can succeed at self-employment?”
While I hate to ever discourage anyone from pursuing their career dream, I have to say the answer to that question is no. Some people just aren’t cut out for self-employment.
I’ve seen a number of people struggle mightily to make it on their own, barely getting by and sometimes reluctantly returning to being an employee when their dream of what self-employment would be like didn’t match the reality.
Table of Contents
- 1. Decision-making
- 2. Networking
- 3. Relationship building
- 4. Communication
- 5. Assertiveness
- 6. Self-discipline
- 7. Resourcefulness
- 8. Creativity
To help you decide whether you have what it takes to succeed at self-employment, in this article I will discuss eight skills that anyone who hopes to make it on their own has to have. These skills are:
- Relationship building
Do you have to be fantastic at all of these skills? No, but you do have to have at least some ability in each of these areas if you hope to build a business that will last and enable you to achieve your long-term goals.
The good news is that each of these skills can be developed over time. You don’t have to be amazing at all of them the day you start out. I certainly wasn’t much of a networker, for example, when I first opened my business.
But I quickly saw how important networking was going to be in building my public relations consultant business and within a few years learned enough to excel at networking.
Let’s look at each skill individually to understand why it’s important to self-employment success.
Most people enter self-employment without thinking about the fact that 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 decide how you’ll spend your time; he/she also decided how whatever budget your company or department had was spent. You may actually have had little experience with making big business decisions – or perhaps even little decisions, depending on the type of work you were doing.
That changes dramatically when you become self-employed. Now you are responsible for every single choice that needs to be made about your business, including how you spend your time and how you spend whatever financial resources you have available to get your business off the ground and to keep it thriving once it’s established.
You decide what customers to pursue, what products or services to offer, where your place of business will be and what you will name your business.
Every day you face choices about the direction you’re taking your business and what you need to do next to move your business forward. These decisions must be made in a timely manner. You also have to stick with your decisions instead of constantly shifting directions. Indecisive, wishy-washy people who constantly change directions have a hard time with self-employment.
Making the transition to being the decision-maker can be smoothed if you understand your decision-making style. For example, 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. You can’t afford to get stuck in analysis paralysis. On the other hand, making off-the-cuff decisions without doing any research at all might not work out well either.
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.
Networking is an essential part of succeeding at self-employment. Yet many, many business people hate networking for one reason or another.
But if you explore the reasons or excuses people give for not wanting to go to networking events, I think you will most often find that the real truth is this: They have never really learned how to network and, as a result, have not been able to overcome their natural fear of making themselves at home in a room full of strangers.
It’s vital to realize that social skills are improved, just like any other business ability. Don’t make the mistake of believing that some people are natural-born networkers and others are not.
My own story proves my point because, as I mentioned earlier, I knew little about networking before becoming my own boss. I grew up in a tiny village in a farming community in Pennsylvania. Until I went to college I almost never had to introduce myself to a stranger; every one for miles around knew my family because my mother taught at the local high school.
This is not an upbringing that prepared me to go out and meet-and-greet situations. While not shy around people I grew up with, I was definitely shy around new folks.
Not being into networking didn’t matter much in the corporate jobs I had early in my career because my work did not require networking. But when I started my own business, I knew I would have to network, network, network to build up my clientele.
I was lucky to meet someone who taught people how to network. One thing she taught me about was facilitated networking. Facilitated networking takes many forms, but basically, they all boil down to having an organized process for helping people meet and exchange information at networking events.
In 1991, I was one of six women who founded a networking group for women on Boston’s south shore. Having seen how well-facilitated networking worked, I lobbied to have facilitated networking be part of each of our events. And I volunteered to be the facilitator for the first two years of the organization. I can tell you story after story of women who joined that group as shy wallflowers but were soon networking like pros. This includes me!
Seeing these members build confidence in their ability to introduce themselves to someone new, present their elevator message about their business, and walk away with a new, potentially helpful acquaintance was extremely gratifying. You, too, can learn to be a skilled networker. Here are the tips that helped me:
Set a goal
Before you walk into a networking event, set a goal for how many business cards you’re going to give out. Do not leave until you’ve met your goal!
Even if you decide your goal is only to hand out three business cards, you may well find that those conversations go so well that you stick around and meet more people. Getting started is the hard part and having a goal in mind helps.
Listen carefully and ask questions
Don’t think that you have to be a sparkling conversationalist to be an effective networker. All you really have to do is pay attention to the other person. Ask simple questions about their work, like how long they’ve been doing what they’re doing and so on.
I’ve found that the question of whether someone is a native to these parts is usually a good question; sometimes the stories of how someone ended up living where they’re living can be quite interesting. In general, do more listening than talking.
Some of the worst networkers I know are people who clearly are not shy. They love to talk, but mostly about themselves and what they do. Don’t be guilty of this.
At a networking function, your purpose is not to sell someone on your services or products. You’re there just to get to know someone well enough so you can contact them later to see if they’d like to meet over coffee or lunch to discuss possible mutual interests.
Look for people who are like you
It can be hard to break into a group of people who are holding a conversation. But look around the room and realize that there are other people there who are probably just as shy as you are; you can find them by noticing who is by themselves. They’ll be happy if you take the initiative to introduce yourself.
Find a networking organization that values your presence
I know from experience that not all networking groups are created equal. In fact, there can be vast differences in how various groups make newcomers feel at home and how welcoming the members are in general.
If you go to a group and find that people are standoffish or don’t seem particularly interested in meeting new people, try another group.
3. Relationship building
Ideally, once you’ve added a new client to your roster, that client will stick around for a good long time. The ability to make this happen will rest to a large degree on your skill in building mutually beneficial and respectful relationships.
Too many times things get off track with a client/vendor relationship not because the work delivered is not good but because the vendor’s manner of dealing with the client is off-putting, clumsy, or even offensive.
On the other hand, I’ve also seen clients keep working with a vendor whose work is sometimes subpar just because that vendor has gone out of his/her way to build a strong relationship that causes the client to be willing to overlook the occasional error.
One of the things I’ve been proudest of in my self-employment years is that I have been able to keep clients for years, even decades, which is unusual in the public relations business, where clients tend to hop around quite a bit.
I attribute this client longevity to the core values that are the basis for how I treat clients. These values have served me well over the years and I think they’ll help you too as you start out on your own.
Be honest in every aspect of your dealings with clients
Always tell clients (and prospective clients) what you really think, not what you think they want to hear. If you’re just going to parrot back to clients what they want to hear and not what they need to hear, save them some money and just shut up. Also, if something is outside your area of expertise, say so and offer to find someone who can help; don’t take work you aren’t qualified for with the notion that you can do a quick study on the topic.
Always do your best
In my line of work, for example, it’s easy to get tired and frustrated by the time you’re on the fourth draft of a marketing brochure or a book chapter. But don’t just start to “mail it in.” Get up every day committed to doing the best you’re capable of doing that day.
If you say you’re going to do something, do it. On those rare occasions when you are going to miss a deadline, let the client know before, not after the fact, and be honest about the reason. Also, be absolutely scrupulous in your billing practices.
Treat clients as you want them to treat you
Clients are more than just a check at the end of the month; they are people who have problems and bad days just like you. So don’t take it personally if they’re snippy or abrupt or not as responsive as you’d like. Don’t take anything personally because it almost never is about you; it’s about them and the totality of their lives, most of which you know little about.
The people issues of self-employment are quite often the hardest to master. In your self-employed life, you will come across all types of personalities and will need to learn to cope with them.
In this context, however, the most important lesson I ever learned is that it is okay – and in fact sometimes essential – to fire a client who treats yours poorly. I’ve fired clients, and even more often I’ve turned down potential work because my intuition told me that the prospective client would not be a pleasant person to work with. Learn to trust your gut on this and you will avoid many bad experiences.
Effective communication is a key component of your ability to build strong business relationships. This is simply something you are going to have to master if you want to succeed at self-employment because you’re going to have to interact with a wide variety of people – maybe not every day but on most days.
From clients to vendors to colleagues to prospects, your ability to share information through oral and written communications will be essential to your success.
It may help to look at some reasons people fail in this area. First, innate shyness may cause you to avoid interacting with others, especially people you’ve just met. This problem will prevent you from creating a business development network that will drive your business forward.
But all is not lost. Shyness can be overcome; I know that for a fact because I’ve conquered that hurdle myself. You can find plenty of advice online about how to overcome shyness. It won’t happen overnight, but if you follow these techniques, you can come out of your shell and learn how to communicate effectively.
Some people aren’t shy but simply have ineffective communication styles. Many of us have walked out of a meeting wondering what exactly the person we just met with was trying to say. You can’t afford to be that person who doesn’t make their messages perfectly clear.
Also, an inability to listen well is another common problem that is very hazardous when you’re self-employed. If you find yourself dominating the conversation in a meeting with a prospect or client, you’re probably doing something wrong.
Finally, regarding communication, far too many people haven’t mastered good writing skills, and this only seems to be getting worse as texts and emails have become the major form of written interaction.
All of your written communication with prospects and clients has to be carefully considered as to its tone and clarity and for its grammatical correctness. Sloppy writing will lead people to question your judgment and your professional skills, which will be the kiss of death to any business.
Fortunately, you can obtain coaching in both oral and written communication. If you think you might need help in one or both of these areas, don’t hesitate to reach out for the assistance you need.
Related: Best Communication Skills Books
Assertiveness is essential in several aspects of self-employment, including the critical areas of convincing people to pay you what you’re worth and then also in collecting what clients have agreed to pay you. You’ll often run into prospective clients who want to get a bargain and who will thus try to get you to charge them a lower price for your products or services.
And, unfortunately, every self-employed person sooner or later has a client who is either chronically slow in paying your invoices or, even worse, decides to not pay you at all. Each of these situations – and many others you’ll face when self-employed – requires at least some skill in being assertive.
I credit my very low financial losses from unpaid bills over nearly three decades of self-employment to the fact that from day one I never hesitated to be assertive about being paid. Payment of my bills is due within thirty days; if I don’t have a check-in hand by day thirty, I e-mail the client on day thirty-one.
If that doesn’t produce an instant explanation, I follow up with a phone call. I do not give up, and I don’t hesitate to be that irritatingly squeaky wheel. A slow-paying client is guaranteed to hear from me every week. I’ve found that such persistence is what is required to get invoices paid.
I have friends who will let weeks (or even months!) go by before they inquire about an overdue invoice. This is foolish. As the time expands between when you delivered your services and when you speak up and demand what you are owed, the odds increase that you won’t get paid.
If you’re the type of person who has a hard time asking for what you deserve when it comes to money matters, then you may have a rocky road if you go the self-employment route.
If this is you, a course in assertiveness may be in order because I guarantee you that sooner or later you will have to stand strong in face of a prospect who wants you to work on the cheap or you will have chase a client for money. Both of these scenarios happen to every self-employed person.
A comment I’ve heard many, many times 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-discipline to be self-employed. I’m not sure I could stay on track. How do you do it?”
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 to do what needs to be done on any given day!
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.
Nobody else is going to be there to schedule new business appointments for you, to go to those networking events you need to go to, and to actually do the work you’ve promised to do for clients – or, equally important, to send out invoices to clients to collect the money you’re owed. It’s all on your shoulders to do the things that must be done for you to stay in business.
Another word for self-discipline is drive. Do you have enough drive to succeed as your own boss? If you truly feel you need external motivation – that you need a boss to hold you accountable for getting things done – then self-employment is not for you.
I wish I had a suggestion for how you can improve in this area, but I honestly don’t. It might be a case the case that you will become more self-motivated as you gain more work experience and become more and more dissatisfied with not having control over your own destiny.
Realizing that your skills aren’t being valued by an employer or that you don’t have the opportunity to move your career in the direction you would prefer it to go in might be what spurs you do become disciplined enough to succeed at self-employment.
You will have a better chance of succeeding as your own boss if you are the type of person who can do a lot with a little. Two resources are apt to be especially tight at times when you’re self-employed – time and money.
The latter – money – might be very tight when you’re just starting out or when a big client gets behind on their payments to you or, heaven forbid, kicks you to the curb in favor of another vendor. And time seems to always be short when you’re self-employed because you’re wearing so many hats.
People talk about making lemonade when life hands you lemons, but being resourceful is really more than that. Resourceful people are able to take a clear-eyed look at their situation and quickly decide how to maximize the value of what is at hand. They adapt quickly when circumstances change – either for the worse or the better – and they apply the knowledge they’ve gained through other experiences to the situation they face now.
If you are afraid to ask for help because you fear people will say no or that asking for help will make you look weak, you are not being resourceful. People like to help others and you’ll find that few people will hesitate to give you advice or recommend someone else who might help you if they can’t do so because of time constraints or other reasons.
Resourceful people don’t hesitate to ask for help when they need it. Perhaps you need advice about a specific aspect of your business. Being resourceful would involve getting someone to mentor you in that area.
If you’re the type of person who doesn’t want to admit you need help, get over it! Never be too proud to ask for help. Very few of us can succeed all by ourselves; realizing that is a vital self-employment lesson.
Finally, let’s look at creativity, which is, of course, closely related to resourceful but also a little bit different than that quality. First, let’s recognize that a huge number of self-employed people work in creative fields – graphic design, web design, writing of all types, advertising, public relations, all forms of the fine arts – the list of creative fields in which you can build a business for yourself is endless. So the very nature of the work they choose requires them to be creative.
But even if you’re not working in one of these creative fields, being your own boss still requires some degree of creative thinking in order to do some of the work you’ll have to undertake to succeed.
For example, you’ll be doing your own marketing and that requires a certain level of creativity. Even just doing a good job with setting up a Facebook or Instagram page that is attractive and draws in viewership requires some degree of creativity.
Thinking outside the box has become a cliché, but it’s a cliché because it’s true! When you’re your own boss you will often need to look at situations in new, creative ways to come up with solutions that will work for you and work for your customers.
Fortunately, you can learn to think more creatively. And you can learn processes that will help you generate more innovative ideas. So don’t worry that you might not be creative enough to make it out on your own; this is definitely an area that we are all capable of improving in if we’re willing to learn some new ways of thinking about the challenges we face.
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