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How to Build Confidence as an Entrepreneur

The idea of breaking away from the corporate world and heading out on our own is very appealing. Most of us harbour secret (or not so secret) ambitions to be our own boss and set the (insert industry here) world on fire with our trailblazing and innovative ideas.  But entrepreneurship is tough, very tough. It’s not for the faint-of-heart. No matter how hard your current job is, no matter how much you dislike your boss, no matter how great your idea is, striking out into the world of entrepreneurship is tough and stressful.

But don’t let this deter you. Despite the (initial) hardships, it’s worth it. Just be sure and set yourself up for success by starting with the right attitude, and an ample dose of confidence (but not the delusional kind). Here’s how to build the confidence you need to get a jump out of the gate.

Start Small

You need to be realistic with what you want to accomplish. Don’t set out to dethrone Apple in the tech world. You’ll fail. Don’t plan to replace The Huffington Post as the source for online news. You won’t. Start small with your plans. Instead of trying to replace Apple, aim to create a better Mail app, or a stronger, open-source and more secure operating system. Or even just a free game for iOS. Small goals are achievable, actionable, and let you quickly celebrate small successes. You’re going to need that.

A word on time frame...you may eventually become the new Apple. Everyone starts from nothing. But you work towards that through an infinite series of small goals. Never set something monumental as your end game. It’s heartbreaking and soul crushing when you fail. Small goals mean success, and success means greater confidence.

Recognize and Plan for Failure

Too many entrepreneurs go charging in with inflated and false bravado. You need to be confident of success, but a smart individual also plans for failure. After all, it happens to everyone. Thomas Edison famously said “I have not failed. I’ve just found 10,000 ways that won’t work.” That’s the attitude you need to embrace. Think of the worst-case scenario in your endeavor. If absolutely everything went wrong, how would you get yourself out of it? Financial considerations, project and production delays, bad press, lacklustre sales...everything. Then, make a plan to fix it. Be specific and concrete. Don’t use tired cliches, promising that if you fail, you’ll “double your effort” or some other platitude. Write out exactly what you would do in each situation to learn from the mistake, and move forward. Once you have that, you have the confidence to do. Failure may happen, but you’re flawlessly prepared for it.

Don’t Be Afraid to Say “I Don’t Know”

Why, oh why, are we so afraid to admit when we don’t know something?! In the entrepreneurial world, too many people see it as weakness. It’s not. It shows a keen business mind, and a confident individual. Lying and making it up as you go along eventually catches up with you. When you don’t know something, admit it. Then seek out someone who does know. Get their advice and expertise.

Far from making you seem unprepared or amateurish, admitting your shortcomings allows you to address them, learn, and improve. And what’s better than that? Not seeing improvement - however gradual - is a sure-fire way to lose confidence in yourself and what you’re doing. Seek out answers to what you don’t know, and your confidence will soar.

Don’t Try and Do It All

The industry leaders that you know and admire don’t do this. New entrepreneurs, eager to prove themselves, often do. Trying to do it all, or too much, is a recipe for failure. The smartest minds out there surround themselves with able experts. They delegate. They ask for input. They collaborate.

Two heads are better than one, right? Sharing the load increases the likelihood of success. Of reaching those (small and achievable) goals that you painstakingly set. Utilise your strengths. Seek answers for what you don’t know. And work with like-minded individuals.


Get out there and experience. Meet people in your industry. Share ideas. Share opinions. Share obstacles and failures. Demonstrate your expertise. Reach out to influencers, in the real world, and online (Twitter, Facebook, Google+, their personal website or blog).

Meeting others doing the same thing as you - or in the same industry, at least - let’s you see that you’re not alone. Your struggles are their struggles. You can feel good about your direction. You gain confidence from being recognised as an expert. Cultivate your authority in your niche. Get your name out there. Create a website to track your progress and growth. Share your experience, and others will reciprocate and comment. Read websites and magazines within your area (Entrepreneur is a great place to start). You’ll gain confidence by simply being part of a community.

Start Before You’re Ready

This last one sounds counter-productive. It’s not. When we’re gearing up for something, we tend to stall. We plan too much. We research too much. We agonise over tiny decisions that should take mere seconds. And during this time, we fixate on everything that could go wrong. It’s a human condition. And the longer you wait, the more you’ll resist. The potential for failure will reach epic proportions in your mind.

So, don’t wait. Just go. I do not, of course, mean leaping in without due diligence. You do need a plan. You do need goals (small and achievable). You do need to anticipate and plan for failure. Just don’t spend too much time on it. Start before you feel you’re ready, because in all probability, you are. Our resistance to change, and challenge, and difficulty is a master of keeping us fooled and believing we can’t do something. Do it. Your confidence will hit heretofore unparalleled heights because you’re doing “it”...whatever that is.

It’s a tough road, this entrepreneurship thing. But worth it. So worth it. Head in with cautious optimism and confidence, and use these tips to build on that. Now go. Do.


Photo by Next TwentyEight

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