Overcoming My Biggest Entrepreneurial Doubts as An Introvert

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When it came to my first foray into entrepreneurship several years ago, most of the time I couldn’t even start.

And, you know what? I think that’s actually the biggest problem for most introverts.

There are many reasons I put the important things off. It would start when I’d think “I need to spend more time preparing” or “I need to do more research.”

Then I’d have thoughts like “I don’t have enough time in my schedule to start a business” and “this is just the wrong time to get into the market.”

Or along those lines: “there’s not even any demand for what I have to offer- why should I try?”

That’s when I’d fall down the rabbit hole. The little confidence and motivation I had mustered would drop off a cliff and my mind became a whirlwind.

  • “Other people can provide this service better than me- I shouldn’t take away from their business.”
  • “I’m not just hurting people by taking away from their business- but maybe I’m leading customers and clients in the wrong direction.”
  • If I fail I’ll look like an idiot. I shouldn’t try. I’ve never been able to do anything like this.”

I’d put things off and put them off and when I did finally start I would half-ass it.

Half of the time I wallowed in self pity, prematurely worrying about some made-up hurdle like the competition or whether I was too early or late to the market.

“This is not the right time” I’d think.

And that too lead me to procrastinate… or at best put forth crap effort and feel like I wasted time.

On a rare occasion I put forth good effort, would be somewhat successful and make a bit of progress- maybe even making a sale.

After I finished I’d think “that felt good but it was sooo draining. I can take a break until tomorrow.”

The next day would come and “I did so well yesterday- a full day off is fine. I’m on a roll, anyways…”

That procrastination rolled over day after day until the momentum completely dried up. I would have fallen far behind by the time I’d finally give things another shot and then consider quitting again.

“What’s the point?! I tried so hard- got out of my comfort zone- but I’ve gotten NOWHERE.”

In reality, it’s not that I’d gotten nowhere- it’s that I’d taken one step forward and three backwards. I didn’t take another the next day. I just stopped working.

Procrastinate, lose momentum and fall behind.

Day after day.

Week after week.

Ad infinitum.

I didn’t think smart or plan things out for business and put forth my best effort.

So if I thought “I don’t have time in my schedule” I wouldn’t look for time- I would just assume there was none.

Or maybe I would try, but not with the intention of “winning.” And it felt like people picked up on that subconsciously (“he’s not so serious about this”).

Sometimes I would avoid the hardest work and focus on the wrong things -à la quick tips from “experts”- instead of relying on my own faculties to plan things out. I’d end up in an endless loop of meaningless research that I didn’t act on.

“I’ll follow these top three tips!”

When it failed: “I’m useless- why am I trying?”

Oh those feelings of uselessness and futility! I was just planning how to plan. And people don’t care what you think and plan- they care what you say and do.

I wasn’t saying or doing anything.

Eventually I realized that I had to change how I thought before I could change what I did. This major fear and doubt I had about connecting with people- it’s just another skill that I can become proficient in.

“I don’t have to master this. I only really need to master something if I want to teach it. Proficiency is enough.”

A famous aphorism that I’ve brought up many times (one that I strongly dislike) is “fake it till you make it.” As cliche as it is, it’s largely true. By forcing yourself to make and take certain actions, you change your perception around them because they create such a large cognitive load.

Even if it doesn’t seem to be a very big step compared to other people, if it’s big and uncomfortable for you it’s going to rewire your brain.

But- and this is a BIG but- you need to have a business plan. You need to take positive action on that on a regular, consistent basis. And you need to review what you’ve done, learn from your mistakes and then try again.

Fortunately, I had a mentor at the time when I was working through this. He pushed me through the discomfort by forcing me to take action and take action and take action.

I had no experience working on my own business. So I had to remind myself that there were many things I hadn’t done before that, after repeatedly taking action (i.e. practicing), I was able to successfully do.

Nobody in my family was interested in the health, but I had taught myself about nutrition, exercise and sleep. And there was a point that I had never driven a car before- but now I’m good at it (at least in my own opinion).

I’d learned how to do things before. The only difference was that the vast majority of businesses involve other people and this venture was no exception.

“Dealing with people” can be the toughest hurdle for introverts.

Therefore, I had to keep in the front of my mind that this is just another skill.

So “dealing with people” became another skill- something that anybody can learn given enough time and the right tools.

Once I had that context and changed my perceptions around it I could start planning things out, working one step at a time through the discomfort and maintaining that momentum, that progress.

Now, I started this venture while continuing to work unappreciated at my full-time job- for many months in fact. Months where I was calling leads everyday and not getting anywhere.

But once the biggest mindset changes started taking shape, I had a first sale.

Then another.

It was still difficult, painful and there were times I was stuck in a funk for weeks.

However, seeing the changes and seeing how I could push the needle. How I could push through these barriers that I didn’t think were possible to push through if you’re “a certain kind of person” made a huge, inspiring impact on me.

Not only that, but I could see that people trusted and liked me enough to give me money for my services.

It was the tangible proof I needed.

Then I had a sale every week. Two every week. On and on.

I ended up being very successful for someone so new to the industry- especially as shy as I was at the time (and, of course, introverted). And it felt incredible.

I was finally able to really push boundaries I didn’t think I could. I could also see that didn’t just have potential in this one thing, but potential for so much growth as a person.

Sure it was very uncomfortable. No- it was downright scary!

Getting things started and pushing through beginner’s inertia was extremely stressful and those feelings honestly never completely go away. It’s just that you expect them and learn how to manage them.

In the worst case scenario- a failure- you simply look back and say “this is what happened, this is what I can learn and this is how I can fix it going forward.”

That change started to feel like an addiction… I needed to constantly move forward.

Every single time I pushed through that daily measurable goal I felt so fulfilled and proud. It motivated me to want to show other people how to do it.

If I could do it- especially coming from where I came from- I knew I could help others get to the same place. Nobody does any good being in a cycle of fruitless planning.

I mean: life is all about moving onto new, better things and growing.

And growing feels great- that drive to take bigger and bigger steps forward.

But… you have to take those first few smaller steps to crush the doubts holding you back before you can make waves.


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