We’re All Insecure When We Start

About a year and a half ago, in November 2013, my wife and I showed up at a bar in downtown Boston for my 10-year high school reunion.

It was a fun night filled with some awesome conversations with people I don’t get to see much anymore, and of course some awkward conversations with people I pretty much never spoke to in high school, but now that we’re 10 years out we act like we’re the best of friends.

There was also the guy who showed up in the suit and tie and wouldn’t stop talking about his high-powered job.

There was the girl who thought it was “super adorable” that I was about to have my second kid and couldn’t believe how much I had “grown up”.

There was the random hook-up and the guy who drank too much. The girl you couldn’t believe was doing so well and the guy you couldn’t believe was still at home with his parents.

You know, just like every other high school reunion ever.

But despite all the fun and hilarity, what I’ll really remember about that night was the intense insecurity I felt when asked one simple question again and again.

“So, what do you do?”

Normal question, right?

We all ask it when meeting someone for the first time or when it’s been a while since we’ve seen them. It’s really just a social convention at this point.

“What do you do?”

But for me personally, at that specific point in time, it was just about the scariest question out there.

I had just lost the only job I’d known since college. The start-up I had been a part of simply didn’t work out and it had only been two weeks since the official end.

And although I was still weighing my options, I was most of the way committed to starting this crazy adventure of building the business I’m running today.

I should have been excited.

I should have talked about all the fun and interesting ideas I had.

I should have admitted that I was nervous, but that I saw a ton of opportunity here and couldn’t wait to get started.

But I’m human. So I didn’t say any of those things.

Instead, when people asked me what I did, for the most part my answer sounded something like this:

“Well, actually, technically I’m unemployed right now, but…”

Why did I do that?

Why did I tell people I was unemployed instead of talking about this exciting new business idea I had?

Why did I sell myself so short?

Well, the simple truth is that I was insecure.

See, I knew what I wanted to do. Starting this business was something I had been dreaming about for years and I was incredibly excited about the possibility of actually getting to do it.

But it was still all so new to me. I was at the very beginning of a completely new and unfamiliar journey. I could see where I wanted to get to, but I could also see just how far away that was from where I currently stood.

And the gap between the two scared me.

I was filled with doubt about my ability to actually do it successfully. And my ego was still hurt from the failure of the startup I had just left.

And on top of all that, my wife and I were due to have our second child in just a couple of weeks, which brought up its own set of questions and anxieties.

So when people asked me what I did, my heart would skip a beat, my stomach would tie up in knots, and I let my insecurity show in full force.

We’re all insecure when we start

Although I wish I had acted differently that night, the truth is that my actions were pretty normal.

Whenever we start something new, no matter how excited we are about where it might take us, we can’t help but see that huge gap that separates where we are now from where we want to be.

As we look at that gap, we start to think about ALL of the things we’ll have to do in order to get to the other side. Some of them are things we’ve never done before, things we’re not all that sure we can actually do yet.

And as we think about all of those things, the excitement of this new venture starts to be replaced by fear, doubt and insecurity.

We start thinking things like “Who am I to think I could actually pull this off?” And “Maybe I should just play it safe and stick with what I know.”

You might have thoughts like this when you’re thinking about getting married or having children.

They may creep in when you think about pursuing a new job or negotiating a raise.

And they can definitely take hold when you start along the path of improving your financial situation and reaching for some of your biggest life dreams.

These doubts, this insecurity, it all sucks. But it’s also totally normal.

And if you want to be successful, your job is to fight it off like all hell.

How to get past the insecurity

So, how can you fight off that insecurity and actually get where you want to go? It’s not easy, but here are a few things I’ve learned along the way.

1. Find someone who supports you

At one point when we were talking about whether I should start my business or get a job for the bazillionth time, my wife finally said: “We have all this savings. If it isn’t for this, then what’s it for?”

I’ll never forget that.

Her support was the real reason I had the courage to take this leap. And it continues to be a driving force behind why I’m still here.

Finding that one person who believes in you could be all the push you need.

2. Focus on small steps

You aren’t going to bridge the entire gap in one day. There’s no single action that will solve all your problems.

So instead of trying to do everything all at once, write down 1-5 things you can do RIGHT NOW to make progress. Then put all your energy into doing those things.

Repeat that process enough times and you’ll be amazed by just how far you can travel.

3. Celebrate progress

Keeping your sights set on your goals is important, but it can feel defeating if you’re always looking ahead.

So take some time to look back and acknowledge the progress you’ve already made AND to appreciate where you are right now. Chances are you have some things you can be proud of, and you should give yourself the same kind of praise you would give to others.

4. Give it time

To some extent, getting past your insecurities is just a matter of time. The more time you spend doing something, the more routine it will feel and the more confident you will be in your abilities.

So again, don’t feel like you have to conquer this all at once. It’s a long, difficult, sometimes triumphant, sometimes discouraging process for everyone, and the longer you stick with it the better your chances of success.

5. Accept that insecurity is part of the deal

I’m MUCH more confident talking about my business today than I was a year and a half ago. But the truth is that I still have many moments of doubt and insecurity as well.

If you’re doing something challenging, those feelings probably won’t ever completely go away. If anything, that doubt can be a sign that you’re on the right path. There wouldn’t be any reason to doubt if you weren’t pushing yourself outside of your normal comfort zone.

Learning to live with those waves of insecurity and keep moving forward anyway is an incredible strength.

What are you going to start?

If you’re starting something new, something you care about, something you’ve never tried before, or maybe something you have tried before and failed, you’re going to feel insecure.

You’re going to doubt whether you can do it. You’re going to have a voice in your head telling you to turn and run the other way.

Everyone feels that way. It’s normal.

But it’s NOT a sign that you should give up.

It’s a sign that you’re on to something big. Keep moving forward.