How to Conquer Entrepreneurial Self-Doubt and Sabotage

Posted by Heather Gray on January 5, 2017 in Career & Entrepreneurship , 1760 words.

Entrepreneurial Self-doubt and Sabotage

The entrepreneurial journey looks something like this…

You get an idea. You start to think about it more and more.

You get excited. You start to research. Your idea builds. You research more. You get more and more excited.

It’s like anticipating a vacation as you add more and more things to your itinerary and wish list. Everything is filled with hope and excitement. Potential is everywhere. You start to dream about your first 7 figure year because, you know, everywhere you go, people are telling you and showing you how it’s possible.

You get to work.

Maybe it’s when you’re staring at your computer trying to do your website DIY style. Maybe it’s after you write your first blog only to realize that the only people who read it were your friends and family.

Whatever it is, overwhelm starts to storm its way in. There’s just so much you don’t know.

Suddenly, it’s like being on an island vacation with rain or a ski vacation without snow.

Everything comes to a screeching halt and there you are.

Welcome to entrepreneurship and the accompanying entrepreneurial mood swings.

One minute you feel on top of the world and the next, you’re wondering what the hell you were thinking. Every little win or success feels incredibly small while every failure feels harshly public as your friends and family start to ask “How’s it going?”

Entrepreneurship is filled with these ups and downs.

Highs and lows come with the territory. In order to stay the course without giving up, the challenge is to stay steady regardless if things are swinging up or down. If you are going to succeed as an entrepreneur, you simply cannot react to every little thing.

You have so much riding on this. You have invested your time and money and you likely have sacrificed time with loved ones. It’s understandable but rapid mood swings can often come with rapid behavior changes and that can damage your business.

You can’t shift the course or plan for your business with every shift or mood swing. If you did, you’d be increasing your ad spend one day and changing your target market the next.

Here’s the one question entrepreneurs need to ask themselves when faced with a sudden high or low:

Is this part of the climate or just a weather event?

If sales or traffic slow for a few days, if you receive a negative review, if you miss a goal, it’s important that you not go into feast or famine mode. That’s essentially a fight or flight response and your behavior and decisions become erratic, impulsive, and ineffective.

Likewise, if you had a goal for X number of orders and you exceed that goal by 75% don’t go charging forward with plans of growth and scale.

New Englanders, for example, know that winters can be hard. They get those annoying Nor’ Easters that dump piles of snow on the region. In the fall, they can have 40 degree days followed by 60 degree days.

They can’t just pack their summer clothes away at the first signs of fall weather because at any point, that can change. That’s why they say “Don’t like the weather? Wait a minute. It’ll change.”

That’s their climate. They can get annoyed, they can poke fun, but they can’t overreact every time the temperature changes. Doing so will leave them unprepared for whatever comes next.

Being an entrepreneur means understanding and appreciating the climate. The entrepreneurial climate includes amazing wins that can easily be followed by crushing losses and vice versa. Things change all the time. Ten seconds ago, Periscope was all the rage and everyone was building their social media following on Periscope. Now everyone has moved on to Facebook Live.

Those types of shifts come with entrepreneurship. They are part of what you are signing up for. People will love you on second and hate on you the next. That, too, comes with the territory. If you are going to succeed as an entrepreneur, you have to accept that that’s the climate you are working in.

When you understand and accept the climate, you can then know, predict, and plan for the weather events that are bound to happen within the climate. Seattle, Washington residents either carry an umbrella regularly or they accept that getting wet is par for the course where they live.

As a new entrepreneur, you may not know the climate of your business just yet. That’s why it’s even more important not to react, pivot, or make a change until you see where everything lands. You need to stay steady, observe, and figure out what it is you need to learn to go forward before you make a move.

That’s how you prepare for storms.


Entrepreneurial self-doubt and sabotage


Failure is part of your climate.

Get used to this. Owners of homes on the water need to know that flooding comes with the territory during hurricane season. They buy insurance for it, they build their homes in ways that can specifically reduce the damage big storms cause, and they get used to boarding up windows.

They do this because living on the water during the sunny season is worth it.

Failure is an inevitable storm you will face so build the insurance policy, make the plans, and get ready to hunker down through it. Know, too, that unlike a hurricane that comes with few lessons, failure is a storm that always comes with lessons and things you can do better next time.

Don’t create your own weather event.

You might remember a science experiment from childhood. We learned to create tornados inside soda bottles. We’d fill the bottle, screw on the cap, turn the bottle upside down and shake and shake and shake until we could see the tornado funnel.

Be careful not to be the source of the storms in your business.

Entrepreneurship comes with anxiety and worry. That excess energy can sit inside you and spin and spin, leading to impulsive behavior and decisions. You can get yourself all wrapped around the axle by comparing yourself to others. You notice this person doing “this” and hear about some other person doing “that” and suddenly, you’re telling yourself a story that you are doing it all wrong.

That’s your anxiety talking, not a real storm and it’s important to know the difference.



To stay steady, you’re going to need support.

It’s all well and good to say “don’t react” but without other tools in your arsenal, it simply isn’t realistic.

Get informed and get educated:

Anyone who starts planning a business without a solid plan, foundation, and knowledge base is set up for failure. Those are the folks that will most likely react as soon as things start to go awry. You don’t have to know everything about everything you are setting out to do but you shouldn’t move forward until you have the necessary base knowledge.

Get a coach or a mentor:

You don’t know what you don’t know. Coaches, mentors, and mastermind groups are your insurance policy against impulsive, irrational thinking. They can hold the big picture for you in moments of doubt and fear. Because they aren’t so close to it, they can sometimes see opportunities or solutions that you might miss.

Know who supports you and who doesn’t:

Part of knowing the entrepreneurial climate will always mean accepting and understanding that not everyone is going to get what you’re doing. Entrepreneurship is risky and the risk averse people will struggle with buying in to your ideas and vision, even if they love you. Know who your people are and lean on them. You don’t have to avoid those who don’t understand your dream. You just can’t rely on them for support with your dream.

Set business hours:

Know when you’re working and when you’re not. If we look at anything under a microscope 24/7, we’re bound to get an exaggerated perspective on every nook and cranny. Getting away from your work for a while will help you see things more clearly. It’ll be easier for you to identify real problems as opposed to self-created or self-imagined ones.

Have a physical outlet:

Exercise is one of the first things people give up when they start new businesses and it’s a mistake. As we know and have talked about here, entrepreneurship comes with a storm of feelings. Feelings are just energy. We have control over how they move in our body and what we do with them. However, if we don’t offer them a release, or some way of escaping, they control us. By scheduling and prioritizing exercise, you are giving yourself a release and that’s so important when you are working to stay steady.

Drink water:

Seriously. I know you just rolled your eyes at that one but here’s the deal. When we are dehydrated, our systems become physically depressed and slowed. We experience symptoms that are distracting like headaches. Some entrepreneurs drink coffee like it’s going out of style. That only adds to the jitters and shakes. By balancing that out with some straight water, you are setting your body up for optimal success.

You’re more than an entrepreneur:

Your business can swallow you whole if you let it. It’s on you to remember who you are aside from being an entrepreneur, dreamer, and business owner. Make sure you still make periodic time for your hobbies. Don’t just read business books or listen to business podcasts. Mix it up. Make time for your relationships, family, and friends. If you balance your life a little bit, things won’t feel so all or nothing when things shift in your business. Remember who you are.


The mood swings are real.

It’s understandable that when something is so intensely personal as your dream and your business that you are going to have moments of overwhelming emotion. You’ll feel elation and fear quite intensely. Make sure you take care of yourself through it. Rather than soothing the feeling with a business move, just take care of yourself. Accept yourself and let that feeling pass as a quick moment.

Your feelings are beyond your control and as an entrepreneur, you’ll get a lot of them. They’ll come swiftly but you are always in control of what you do with them. Keep your eye on the prize and on your goal. You don’t have to let your feelings run the show.

Stay in control. Stay in your own lane. You’ve got this.

If things feel bumpy, pull over and regroup. Ask for help but keep moving.

So long as you never quit, anything is possible.


Feature illustration by Allys Pineda

About the Author

Heather Gray Profile

Heather Gray is an executive coach, therapist, and writer with 16 years of clinical experience. Heather regularly writes for Huffington Post,, and She is also a Lead Editor and contributing writer for The Good Men Project.


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