The Best Way to Overcome Obstacles in Life

It was late October, and we were facing a crisis. One of the major tours that we had been planning for well over a year was falling apart.

Due to a perfect storm of challenges, the tour could not be salvaged unless we could raise $50,000 practically overnight.

Have you ever been in this boat? Think back to times you had to overcome obstacles in life — whether in your career, a relationship, or school.

Do you remember how you reacted to those challenges?

Typical reactions include everything from ignoring the problem to overthinking it. Maybe you can relate to some of these common thoughts:

I don’t know how to solve this problem! I know it will damage my reputation, destroy my income, ruin my chances… fill in the blank.

It’s no use, I should just quit.

Why does everyone else have it easier than me? I can’t handle this.

If any of these thoughts sound familiar, don’t worry. You’re not alone. Having to overcome obstacles in life brings up fear — and fear brings up strong reactions.

Reactions That Don’t Help You Overcome Obstacles in Life

Worrying about the consequences of an obstacle pulls you out of your present power and creates unnecessary drama.

Using the first example above, if your reputation isn’t damaged now, if your income isn’t destroyed yet, then it’s not time to worry about those things. Doing so will only exacerbate the problem.

Dealing with our tour, I came up with all sorts of doomsday scenarios. The venues had already announced the concerts and started selling tickets for them. I imagined an upset crowd mobbing the venue, demanding their money back. I envisioned an overwhelmed presenter who swore that he would never work with us again. But that was all in my head.

Giving up or ignoring obstacles won’t really solve the problem either. Most of the time it delays the inevitable — and often, makes it more challenging than it would have been if you faced it head on.

Comparing yourself to other people is a way to shift the focus off of your own power. It’s a tricky distraction that makes you feel like a victim — like you’re powerless to affect the outcome of your circumstances because things just happen to you and they don’t happen to anyone else.

None of these options will help you overcome obstacles in life with ease. But there’s a better way to handle uncertainty and frustration.

Lean into Your Discomfort

It might sound counterintuitive, but leaning into your fears, discomfort, and anxiety can help you overcome obstacles in life much quicker.

Here’s why: letting yourself feel your fears (rather than looping your thoughts around those fears) brings your emotions to the surface where they can be released.

After this release, you’re left with more clarity, focus, and energy.

Let’s break this down further:

First, let your emotions be your emotions. Don’t attach stories to the feelings — simply feel them and process them. Do that first, before taking any action.

Once you have fully processed things emotionally, realize that this will not make or break the rest of your life, unless you let it.

Commit to bringing the crisis to conclusion, and — this is key — do so even if conclusion is unfavorable for you. Conclusion is the goal.

Decide that you’re committed to solving this now and don’t make up stalling techniques or excuses as to why it’s better to wait to handle it later.

Lastly, bring other people in. Dealing with our tour debacle, the last thing that I wanted was to alert the venue directors (who were trusting us to ensure that the artists would make it on the tour as planned) that the upcoming tour was at risk.

That said, once I finally took a breath and made those crucial calls, I learned that I had partners in the venue directors, not adversaries. When I brought them into the challenge, we got their heads together and they actually helped us brainstorm and explore solutions.

Be Open to Introspection

When Jennifer and I run workshops, we often put our participants through the paces by breaking them up in pairs and helping them think of ways to overcome obstacles in life in new and exciting ways.

Often, these lead to major aha moments. Frequently, one of them will raise their hand and say, “Wow, this is amazing! Do you two do this all the time? How do you handle all that introspection?”

After enough practice, introspection and “leaning in” doesn’t feel like a lot of work! It becomes a natural, welcome way to process our experiences, emotions, and circumstances.

In reality, doing this work makes life easier. You put up less of a fight. You accept reality and think of creative solutions to what some people might call “problems” (but you see as opportunities).

Here’s a great example we heard from Michael Drapkin:

A major milestone in skiing was taking a lesson where my instructor made me lean into the fall line rather than always fighting it. From then on, that downhill pull of gravity started to work for me instead of being afraid of losing control, and the mountains suddenly felt flatter.

A crisis can be a signal for you to lean in, rather than fight.

How Do You Overcome Obstacles in Life?

What’s your typical response when faced with a crisis?

Does your usual response help or hurt in the long run?

Leave a comment below.