How to Build More Career Confidence

​On a recent trip to Panama, my travel companion and I climbed up a volcano in the middle of the night that reached over 11,000 feet in height.

​Rain was penetrating us from all sides, and the flimsy poncho I bought last minute was proving to be insufficient in the face of intense rain and wind. My tights were soaked, my head was cold, my hands were chilled, and I was nauseous and throwing up from alpine sickness.

At the summit, there was nothing to greet us other than more rain and wind — no sunrise was to be seen other than the black sky slowly turning a dark, cloudy grey. We were fortunate to catch a ride back down the mountain in a 4x4 — a serious lifesaver after 6 hours of uphill climbing, unable to retain any food or water.

Back at the bottom of the volcano, we head to Boquete — a cute little expat town we’re staying in for a few nights. At dinner, I order a glass of water, “Una agua por favor.”

I get a weird look from the server and upon a quick look on Google translate, I realize “Un agua por favor” makes more sense — a nuance of the language I could have only learn from getting a weird look.

On our trip, we also visit the tropical islands of San Blas, where there’s over 350 islands spotting the ocean, most of which you can walk the perimeter of in ten minutes or less.

Sitting in a tiny speedboat, with only an overhead tarp to shelter us, I notice my raincoat (that I’d bought specifically for the trip) is soaked through. Apparently not all raincoats are waterproof in torrential downpours?!

Just outside of Panama City, we decide to go for a hike through the jungle in a nearby park. I’ve worn my Blundstone boots with high ankles and low-cut runners’ socks. I quickly realize this is an equation for mad blisters on the back of my calf. (It hurts!!)

Stopping in the middle of a swarm of ants that make it look like the ground is swimming, I bend over to take a video because it looks so interesting. However, it doesn’t take long for the ants to start crawling up my boots, down my boots, and along my legs, biting me in the process. (Again, it hurts!!)

Noticing a theme here?

Lots of mistakes. And a lack of preparedness — because how can we be prepared for the unknown and unfamiliar?

During this two-week trip to Panama, we got a lot wrong. But I wouldn’t change a thing because I’ve learned so much:

• Some basic Spanish
• The importance of having proper rain gear (and that there’s different levels of “waterproof”)
• Alpine sickness can hit anywhere above 8,000 feet (and I’m more sensitive to it than most people)
• If you stop in a swarm of ants, they will crawl up your legs and bite you
• Proper hiking gear is essential and worth the extra space it will take up in your backpack

Ok, so how is this related to career?

It really struck me on this trip how much we learn through mistakes.

If we’d had sunny skies, proper raincoats, and perfect Spanish on the first try, we would have had a more comfortable trip for sure, but we wouldn’t have been nearly as prepared for the next time we travel, hike, and converse in a different country with less-than-ideal conditions.

Now we know how to prepare better in the future AND we feel much more resilient.

It’s the same when it comes to career — or anything in life, for that matter.

There are no wrong decisions because mistakes only lead to greater learning and the knowledge that we can handle the more challenging experiences that come our way.

Imagine this: you get the exact job you want right out of University. You get along with your coworkers, you have a great relationship with your boss, and you excel in your role. You feel confident and on track. Eventually, you’re promoted to Manager, then Senior Manager, then VP — with lots of ease. You like your job, but you aren’t particularly challenged. You aren’t sure you deserve the title you’ve been given and that you’d be able to perform at that level outside of your current company — because you’ve never had to!

Suddenly, you learn that the company is being bought out and your position has been eliminated — how do you feel?

(By the way — I’ve heard this tale many times, from many different clients.)

Now, imagine an alternative scenario: you don’t know what you want to do after college, so you float around from job to job. You try many different things and by the time you’re 30, you’ve had over 30 different jobs. You feel confident in your ability to find and land opportunities, and you know you can kill it in an interview — even if other people look at you as a bit directionless.

One day, you land a great job as a Manager at a company you love. You’re quickly promoted to Senior Manager and shortly after, you find an opportunity as a Senior Manager at another company you’re even more crazy about. You move into a new role, but find it isn’t quite the right fit, so you take a stab at applying for a VP role at a company where you know the President. You’re over the moon when you find that you’ve landed the role!

After a few years, living it up in your dream job, you learn that the company is being bought out and your position has been eliminated — how do you feel?

It seems clear that the person in the latter scenario has built more resilience for themselves in their career — but their path and journey has also been much more challenging.

Who would you rather be? Who do you think has a better understanding of themselves? Who do you think has grown and developed more? Who do you think, upon the announcement of an unexpected layoff, will be more equipped to seek out the next opportunity that’s a good fit?

It’s often the wiggly-squiggly path (as opposed to the linear one) that provides the greatest fulfillment. It’s simply a matter of knowing how to connect the dots and be self-reflective along the way so that the most learning, growth, and resilience may be gained.

Uncertainty about the future is always lurking around the corner. It’s only through taking action, trying different things, and making lots of mistakes (and then some more mistakes) that we can build resilience and reduce the fear that lurks in the face of inevitable uncertainty.

If you’re feeling stuck in your career and lacking confidence, try something new. Put yourself in an uncomfortable position. Follow the path where you feel least confidence, and from that, build the confidence that you can handle new situations and challenges.

As I once read on a t-shirt, “Nothing great ever comes from being in your comfort zone.”

We must move through discomfort and a lack of confidence in order to build confidence. Action is key.

Don’t get stuck in the when/then scenario. (E.g., “When I have more confidence, then I’ll go out and start meeting new people.)

As someone who’s had over 30 different jobs before I turned 30, built up a business from scratch with no business experience or pre-existing knowledge, and designed one-on-one coaching programs purely through trial and error — I can personally attest: this shit works.

And let’s not forget all the mistakes that happened on my recent trip to Panama.

Oh, how I love you mistakes — keep ’em comin’ 😉