10 Ways Entrepreneurs Sabotage Their Success

One night you go to sleep thinking you have it in you to take over the world, to build a great business, to build great relationships, to have a great family. Then you wake up the next morning and nothing makes sense…


You start asking yourself “Why? Why me? Why should I sign that contract? Why should I marry that person? Why should I keep going?” You question your first big sale, you question the business model that is actually working, you question everything, including yourself. All of the sudden, you no longer deserve the contract, you no longer deserve your significant other, you no longer deserve your success. Distractions and fear come in.


If you have ever felt that way, I want you to take a deep breath and know that you are not alone. Almost every human being has at least once felt one of the above. The difference between those who make it and those who don’t is the fact that those who make it don’t allow those doubts and feelings of self-sabotage to stop them. Why should they, anyways? Why should you?


Below are the 10 ways entrepreneurs sabotage their success. Read them, internalize them and do the exact opposite.


Harradox Images

Harradox Images

1. Keep saying yes to everything. Know that you have a very limited and precious amount of time and resources on this earth. Spend them accordingly. If you keep saying yes to every request, to every project, and to everyone, sooner than you think, not only will you be in a perpetual frustration mode, but you won’t have time to do what matters most. A good measuring stick for this is: If after you said yes, you felt angry for saying it, you probably shouldn’t have said it. Sounds common sense, but common sense isn’t so common these days.


2. Don’t show up for your appointments. People are expecting you? No worries. People are counting on your for something? No worries. You have promised something to someone and don’t feel like following through? No big deal, right? Wrong. There is absolutely no excuse for the “sorry, I forgot.” I once hired someone to do a simple banner work and he was a no-show for two appointments. I immediately cut ties with him. When a friend came to me asking if I knew someone trustworthy to interview for a very lucrative media project, guess who I recommended? Not that guy. Referral and word-of-mouth are the best forms of winning business. Show up. Be present. Do what you said you would do.


3. Compare yourself to others. Johnny has nice benefits, a “safe” job, and he just got a nice raise while you are working 14 hour days, most of which are paid in sweat only, in your start-up. You look at him and say, “What am I doing with my life?” Don’t. Just don’t. When you start to wonder in those terms, stop. You shouldn’t care about Johnny at all. You should care about yourself, your family and your customers. Society has done a good job of making you think you should act and feel a certain way, and that if you don’t, there’s something wrong with you. There is nothing wrong with you. Don’t compare yourself to anyone. Ever. You should be your priority. Put some horse blinders on, ignore the distractions around you, and keep hustling.


4. Don’t believe in your product or idea. If you don’t believe in your stuff, who will? No one. If your eyes don’t shine and if you don’t get as excited as a 5th grader talking about their love for insects as you talk about your idea, then something is wrong. If you are not passionate about it, no one else will be. It all starts with you. The moment you start passionately and enthusiastically talking about your project, it will rub off to others. They will be your customers and evangelists for life.


5. Keep thinking that you’re bothering people. A friend once told me he had a problem contacting prospective clients because he always felt he was bothering them. He never got any clients. He let his vision fade away because of what he thought others thought about him. A lack of self-esteem will ruthlessly bring you down. Be careful.

6. Have no clear idea where your business, and your life, are going. A well thought-out plan is an absolute must. You have to know where you are going if you ever want to get there. As a fellow author once put it, “A man/woman who aims at nothing, hits it with amazing accuracy.” Do leave some room open to serendipity and to occasional twists and turns – you will change direction many times and your vision will evolve – but if you don’t set out a destination, you will be stuck. What’s worse, you will reach results and places you dread.

7. Promise the world and deliver a city. Never, ever tell anyone you can do X, Y and Z and end up delivering half of X. Be more than that. Promise little. Then wow your customers, friends and family by always delivering way more than expected. Zappos has mastered this art pretty well. They promise a pair of shoes will get to your house in five days. Three days later, you get your shoes in the mail. Sometimes they also upgrade you to overnight delivery without your knowledge. That’s why they are so successful and that’s why they have customers for life.


8. Keep procrastinating. That’s the most common form of self-sabotage. We are always waiting for the ‘perfect’ conditions to start a project, or to simply fulfill existing ones. Our brains are lazy. They look for the easy way out. They don’t like change, or hard work. Fight those feelings. You’re bigger than them. Train your brain to withstand the pain of starting projects whenever you have to, instead of whenever you feel like it.

As Pablo Picasso once said…

Harradox Images

Harradox Images

Inspiration exists, but it has to find you working.


9. Just don’t finish the stuff you started. A fast way to fail is to never finish what you started. An even faster way to fail is to start several things and never finish any of them. Don’t waste your energy, and time, on many things. Start one thing, finish it, and then move on to the next project. Be a master of one thing, not a jack-of-all-trades who knows nothing deeply about any of those subjects.


10. Treat your customers poorly. Well-Fargo will never have my business just because of one bad encounter – that could have easily been avoided – with one of its branch managers. Today’s markets are relationship-based. You don’t have to agree with everything your customers say, but you should always greet them with a larger-than-life smile and with a warm handshake. They are the reason you are in business. Your customers are the reason why you are able to pay your bills. Treat them well. Also, treat each client as if he/she were your highest-paying one. If you do that, I promise you will get more clients, faster, and get more business from the existing ones.