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7 Ways You Are Sabotaging Your Own Business

7 Ways You Are Sabotaging Your Own Business

One of the first times I ever spoke to a potential client over the phone, she was almost ready to hire me when she asked, “Is this what you plan to do for the rest of your life?”

I was completely caught off guard. How was I supposed to know? What did it matter what I wanted to do for the rest of my life, after all? How did that affect my ability to write for her now? Why was she making me so uncomfortable?

If I had been better prepared, of course, I would have realized that what she really wanted to know was how committed I was to this work. Did I care about it? Did I invest time and money into improving myself? Would I do a half-assed job and leave her to clean up the mess? Was I a professional or a dabbler?

I don’t actually remember what I said, to be honest. But I know it was pretty stupid, and probably a little defensive, and that I didn’t get the job. I didn’t inspire confidence in myself and my work, so she took her business elsewhere.

I sabotaged myself.

When you work for yourself, it’s amazing how often that can happen. I see it all the time on websites and in emails. I see small businesses failing to inspire confidence in their work, freelancers panicking and losing clients for no reason, writers who feel uncomfortable asking for what they are owed. And the worst part is, they don’t even realize they are doing it.

If your business is failing to grow, you could be sabotaging yourself without realizing it.

How? Probably by doing one of these seven things.


1. Dismissing yourself

Have you ever told a potential client, “Well, I’m pretty new at this, so I don’t know much about…” or something similar?

Don’t. Stop that. Right away.

When you dismiss your own work, you don’t give a client any reason to trust you or take you on. Put another way, if you don’t sound like you have confidence in yourself, why should they? Instead of talking about what you don’t know how to do, or how inexperienced you are, talk about your accomplishments. It’s not that you don’t know anything about long-form articles, it’s that you specialize in blogging. And by the way, you’re always willing to give something new a shot, right?

2. Sharing unhelpful information

This includes such gems as “I began freelancing because I couldn’t find another job” and “This is the fourth business I’ve started, I’m really hoping this one finally works out.”

There’s nothing wrong with trying out a new idea when the old one didn’t work. And starting your own business when you can’t find work is not a bad idea. But do you need to tell potential clients or new colleagues that? No, not really. Sharing unhelpful information can seriously hurt your chances of landing new work, making you look unprofessional at best and incompetent at worst. Keep the information you share positive and leave out the unhelpful stuff.

3. Demanding work

Here’s something important to remember: No one owes you work.

Not the editor that you emailed, not the friend who works at a big company, not the new client you’re courting. They don’t owe you anything (except to treat you like a human being and to pay you if they do hire you.) Don’t treat them as if they do. Don’t harass them if work is not forthcoming. Don’t insist that they explain in minute detail why they decided not to work with you. Be professional and polite and move on.

As a bonus, demanding work makes you look desperate, but acting like you don’t need it makes you look like you’re already successful. Which makes people want to work with you even more.

4. Not following up

The flipside of that, of course, is that you should follow up politely when an opportunity presents itself.

Add that new colleague on LinkedIn. Send a new pitch to an editor that rejected your first one. Reach out to a lukewarm lead at a later date with a new offer. You’d be amazed how much work you can land just by waiting a little while and then following up. (Respectfully and politely, of course.)

5. Going MIA

I’ve admitted before that I am terrible about expecting bad news. At least 50% of the time I assume emails from clients are going to be negative and get scared to open and read them. But guess what? I still have to. Because going MIA is far worse than getting something wrong.

If you are working with someone, keep in touch. Send them updates. If something goes wrong, or you’re going to be delayed, or a product is no longer available, tell them. Apologize, and do what you can to make it right. Disappearing will not prevent them from noticing that something went wrong. It will make you look bad and cause you to lose business. But if you reach out and keep in touch and explain yourself, you’re far more likely to smooth things over and keep the client.

6. Ignoring guidelines and instructions

Did your client tell you specifically how they want something formatted? Does the website you’re pitching have set writer’s guidelines? Did a new client ask you to contact them by phone rather than email?

And did you do it your way anyway, just because?

Whether through laziness, inattention, or that-applies-to-everyone-but-me-ness, failing to follow instructions or guidelines is just annoying. It’s not cute, it’s unhelpful, and it slows everything down. If there are instructions or systems, odds are, they are there for a reason. (Even if that reason is just to weed out people who can’t or won’t follow instructions.) You should follow them. It will make everyone’s lives easier, make you look better, and leave you far more likely to get the work you’re looking for.

7. Not invoicing

It’s amazing how many small business owners, and especially freelancers, are afraid to ask for the money they are owed.

Do it. Send those invoices. If they’re not paid, follow up and send them again. You did work, you are entitled to get paid for it. Don’t immediatelly treat someone like they’re trying to rip you off, of course, because there’s a good chance they did just forget. (My first “you didn’t pay me” email has the subject line, “Whoops, looks like you forgot something!”) But it’s okay to insist on payment, firmly and politely. This isn’t like hounding a friend for the five bucks they owe you. This is the difference between paying your rent and not. Don’t be afraid to invoice.

Do you have any self-sabotaging habits that you need to break?

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