5 Ways You’re Self-Sabotaging Your Chances of Success

A Few Things You Can Do to Stop

I’m coming to the end of my first week as a freelance writer. I’ve spent months reading all the “how to…” articles on Medium, networking, planning, and setting myself up for a smooth start.

I’ve been lucky enough to meet some amazing writers, who are even better people, including Matt LillywhiteClaire StapleyStephen Moore, and Jon Hawkins, who have given me invaluable advice and encouragement. I was confident that I was all set up. I was ready to go. And yet, it hasn’t felt like a smooth start at all. Does it ever?

It’s Day 5 and I’m already failing to apply an important piece of advice. It’s something that anyone aspiring to be great at something needs to do. To achieve success, in any area, you need to actually make a start.

“The secret to getting ahead is getting started” — Mark Twain



It may seem obvious, but it’s easier said than done. Starting something new, especially something that you’re passionate about can be petrifying. Why? Because when you aspire for success, whether you realize it or not, you’re vulnerable. Vulnerable to failure; vulnerable because you’ve taken yourself out of your comfort zone; vulnerable because you need to take risks. You feel completely exposed, so it’s easy for things to shake you and knock you down.

The good news is, that this is something you can overcome. Because that ‘thing’ that shakes you and knocks you down, is often just you.


Making a start

Why is it so hard to make a start? Even when it’s something you’re excited about, there’s a pit in your stomach that makes you hesitate. It makes you procrastinate and come up with excuses to justify why ‘now is not a good time’.

I’m definitely guilty of this. My plan this month was to juggle client work and write on Medium. Following Tom Kuegler’s advice, my target was to write 5 articles for Medium a week. You can probably guess what happened. I prioritized client work. This is my third Medium post this month, and we’re two weeks in. I failed to hit my target just because I couldn’t find the courage to make a decent start.

It’s strange because it wasn’t something that I could even really ‘fail’ at. The only thing that stopped me from writing 5 articles per week was me.

Have you ever experienced something like this? A sense of frustration because you know that you’re the only one that’s holding you back, but at the same time, you’re not sure why you’re doing it?

Well, you’re not alone. Have you ever heard of the impostor syndrome?

The Impostor Syndrome

It’s a psychological phenomenon used to describe high achievers who deep down feel like complete frauds. Like their accomplishments are a result of luck; luck that will eventually run out, and they’ll be found out.

Dr. Valerie Young has identified five different types of impostor syndrome. I identify pretty strongly with two of these. Let’s see if you see yourself reflected too.


1) The Expert

‘Experts’ feel as though they need to be completely prepared and know absolutely everything there is to know about something before giving it a go.

The other day I wanted to write an article about ways in which we can reduce the negative impact we’re having on the world’s oceans. Why didn’t I? Because I’m not an environmentalist. Who’s going to read my article if I don’t have a Ph.D. in how to chemically engineer biodegradable plastics?

How to Overcome it

If you feel like this too, know this. Anyone can write about anything. Your experience and your opinion is just as valid as anyone else’s. By all means, if you’re relying on research, cite your source. But you’re free to interpret the facts and express them however you choose. You’re never going to feel 100% ready so just go for it.

“You don’t need to be an expert in something to try it” — Michael Bloomberg


2) The Perfectionist

The other category I fall into is that of ‘The Perfectionist’. This isn’t me trying to come up with a lame response to the “What’s one of your weaknesses” question in a job interview. It’s me telling you that this is a genuine weakness. And, it’s a weakness of mine.

Perfectionists feel like they can always do better; there’s always more they can do. But it’s not productive or healthy. You can wear yourself out and lessen your chances of doing the best that you can do because you’ll be exhausted!

When it comes to client work, I probably dedicate more hours than I really need to (in my quest to make each piece perfect). By the time I’m done with that, it’s late, I’m exhausted, and I can’t find the energy to do what I really want to do, which is to write a truly valuable piece on Medium! I sometimes start a piece, only to hit ‘Select All’, ‘Delete’ when I realize it looks like it’s been written by a six-year-old.

How to Overcome it

For those of you who might be feeling this way, remember that perfection doesn’t exist. Therefore, anyone who seeks to attain it is bound to fail. By definition. You can’t attain something that doesn’t exist; that’s unobtainable. All you can do is work to the best of your ability, and do the best that you can do with what you have.

Throw yourself into the deep end and force yourself to act even if you don’t feel 100% ready. Don’t be afraid to fail, and consider it a part of the process. In fact, it could even help to plan to fail. I’m not kidding — factor in some “additional time” into your plan so that you know that you’ve got a little room for error. That way, you won’t be afraid by the prospect of making an error, and you’ll know you’ve left enough time for correction.

“Perfectionism is not a way to avoid shame. Perfectionism is a form of shame.” -Brené Brown


3) The Superwoman/man

Do you feel stressed when you’re not working? Are you someone who sees downtime as a complete waste of time? There’s so much work that you could be doing instead of going to that art class you used to like; let’s face it you’re never going to be an artist, so what’s the point?

The superwomen and supermen among us are those who feel like they haven’t really earned their title; like their colleagues are actually more competent and they need to work extra hard to prove themselves. But this over-work is just a false cover-up for their insecurities.

If you see yourself reflected here, know that this work overload can harm all of the other aspects of your life that you’re neglecting. This includes your mental health, your physical health, your relationships. You could wake up one day and realize that the only thing you’ve cultivated in your life is your work. You have no hobbies, no passions, no interests…

How to Overcome it

I received some wise words of advice from an inspirational woman that I now consider a life-mentor. Her name is Laura Sheehan, and she essentially dedicates her time towards helping people find fulfillment in life. The exercise that she made me do will work wonders for all the superwomen and supermen out there.

She asked me to make a list of my ‘core values’. A list of words that represent the things I value the most in life. Elements that I simply don’t ever want to be missing from my life, or characteristics that I want to uphold no matter what the circumstances are. To give you some examples, these can range from — Family, Love, Generosity, Tolerance, Peace, Health…

When you work towards becoming the best version of yourself; the best person that you can be, being the best at work will no longer worry you, because your career becomes just one of the elements in your life. You’re working hard to uphold your values, and live the life that you want to live. And remember:

“No one on his deathbed ever said, ‘I wish I had spent more time at the office” — Paul Tsongas


4) The Natural Genius

These are the people who think that you need to be a natural genius to do a particular thing. They think they’ll only be successful at the things that come easily and quickly to them. So, these are the people that easily feel discouraged when they try something new and see that it takes then a while to master. They feel ashamed and give up before they’re able to reap the benefits of their efforts.

How to Overcome it

You need to see yourself as a work in progress. The reason why you’re not succeeding is because the level of achievement you expect right out of the gate is impossibly high! Think about the hours and hours of training that top athletes go through to prepare themselves for a single game or a race. They spend hours and hours practicing before they succeed.

Try setting milestones for yourself along your journey to success. Start off easy, and incrementally build your way up. This way you’ll be able to observe the incremental progress that you’re making, and you’ll feel encouraged to keep going!

I think generally…real change, enduring change, happens one step at a time” — Ruth Bader Ginsburg


5) The Soloist

This describes the stereotypical TV-Dad that refuses to ask for directions, refuses to call a plumber, and throws away every instruction manual. It’s the typical person that feels as though asking for help is a sign of weakness; they refuse to accept that they can’t do it all.

The thing is, even in times when you do start, you’re making things harder for yourself. You’re likely to invest a lot more time and effort than you really need to. Although you might think that you’re being hands-on and productive, you’re really just covering up your insecurity, when in reality, you could obtain a better and quicker result if you just ask for help.

How to Overcome it

Make a list of your strengths and weaknesses. Focus on applying your strengths to get the job done, and leverage the knowledge and experience of others to help you learn and supplement your weaknesses.

Don’t be afraid to ask questions. Don’t be afraid to ask for help when you need it. I do that every day. Asking for help isn’t a sign of weakness, it’s a sign of strength. It shows you have the courage to admit when you don’t know something, and to learn something new” — Barack Obama.


Don’t stand in your way

These categories aren’t all bad. If you identify with any of these groups, you’re probably someone who’s ambitious, who constantly pushes themselves to be better, and that’s a great way to be! Just remember not to wait to be the best before you even get started, because the things that you learn along the journey are the things you need to learn to be great!

I put my faith and my trust into those who advised me; those who are killing it as writers! Be consistent, and trust that you’ll only get better with practice. One day, the compound effect will work in your favor, and you’ll be able to reap the benefits of all your hard work. So shake off any doubt that you have in yourself, and make a start.

“Doubt Kills More dreams than failure ever will” — Suzy Kassem

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