My 3 Biggest Failures In 2020

Do you feel limited by the job titles and career paths you’re seeing?

I’m a planner and a dreamer. I love thinking about the future—all the things I want to create, and, yes, all the bad things that could happen. This has its pros and cons.

That said, I do love a good look-back: revisiting my original plans and dreams to see how they actually unfolded.

You know what they say about best laid plans…2020 was an unprecedented year.

It makes me sad to see people write off the entire year, universally condemn it as horrible, or attempt to “just get through it.” To me, that misses a huge opportunity for important reflection that helps us move forward.

And, especially for high-achievers, it’s critical to remind ourselves—and actually celebrate—all we have accomplished. Since it felt like all of my plans were canceled (and involved travel, large gatherings and/or restaurants), I was shocked at how many goals I actually met.

(Important caveat: if you’re currently in the sh&!, now is probably not the time to reflect. Take care of yourself, and you can reflect once you reach the other side.)

I bring you my 2020 reflections and 2021 plans in two parts—

  1. Failures and Lessons

  2. 2021 Goals

Failures and Lessons

I had three big misses in 2020:

1. Meeting a romantic partner

This was one of my top goals this year. And I FAILED.

Because I’m a loser and no one will ever love me.

(I do not actually believe this. But isn’t it interesting how we often make our failures mean something bad about who we are?)

Dating is not my strong suit. The pandemic didn’t help.

That said, the pandemic is not the reason I’m still single.

I’m fairly certain I’d have missed this goal anyway. Because I have some pretty sticky limiting beliefs about the process of dating and what’s possible.

The lesson: there’s a difference between intentionally de-prioritizing your goals because you choose to spend your time and energy elsewhere versus allowing limiting beliefs to de-prioritize them for you.

For me and dating, it’s a bit of both, so I’ll continue taking steps in 2021.

What goals did you consciously modify this year? Be honest, which ones were actually delayed because of fear and/or limiting beliefs? Which goals did you revise due to 2020 events and find a different way in?

2. Writing a book

I did not write a book this year.

I was iffy on my commitment to this goal even as I was setting it. But I ignored that inkling and made it a goal anyway.

The thing is, I’m a doer. So if it’s on the to-do list, I want to get it done.

So even though I wasn’t fully committed, I felt compelled to follow through.

Here’s where patience comes in—and where I feel like I failed upward on this goal. Because I didn't force it just to check the box and say I did it.

The more I step into creativity and entrepreneurship, the more I learn to create space for things to unfold. The word “trust” comes to mind.

And, the more I practice moving toward something without forcing it, the better the result—and the process of getting it.

Even if that means taking the L on the original goal.

I’m going to follow my intuition in 2021 and be okay with not having a book goal this year either. It will happen.

What are you ready to commit to in your career—truly commit—in 2021? And where might you practice patience?

3. Meeting my stretch income goals

I set 3 income goals every year - one that’s aspirational, one that’s a stretch but has clear path to achieve, and one that’s the minimum I need if the bottom falls out.

This was a bottom-falling-out year. (Luckily this is one of my biggest fears, so I’ve literally been anticipating and planning for it for years.)

I met my minimum income goal, and I’m okay with that.

I even turned down a lucrative opportunity that wasn’t aligned with my values.

(Honestly, there’s no bigger power move than walking away from money because you know you can make it in a way that also feels good.)

The lesson I hope you’ll take away is that you can always find a path forward financially, so you might as well find it doing something you love.

Plus, it’s a great reminder that even the worst case scenarios aren’t nearly as bad as we imagine, especially when we plan for them!

Let’s Normalize Failure

Failure is simply one of many steps on the path to success.

It makes me feel so powerful to publicly post my failures. 💪

Although not gonna lie, there’s still a part of me that feels a little weird…like I should post 3 successes for every failure to prove myself, like admitting failure detracts from my credibility, like entrepreneurship is supposed to be travel and glamour and 100% living my best life (I see you, limiting beliefs!)

But that’s not real life. No career worth having exists without some failure.

I used to be so afraid of failure that I wouldn’t even try. Or only set goals I knew I could meet. (?!)

What a small and inconsequential life.

And if one of the things you’re searching for more of in your career is confidence, well…

…Imagine being okay with setting BIG goals even if it means you might miss them because they’re worth going after and you know you’ll meet them next time.

…Imagine not letting money concerns take you down the wrong path…and knowing you have the power to make as much money as you want the way you want to.

…Imagine trusting your intuition and committing to what you want because you know you’ll be successful—even if it’s different from how you planned it.

That’s confidence.

What would you do in 2021 if you weren’t afraid to fail?

The absolute worst thing we can do is sink into embarrassment or shame when we try and fail.

What if, instead of trying to hide your misses, you shouted them from the mountaintops? Seriously. Would people gather to point and jeer? Probably not.

What would you do if a colleague or loved one shared a failure? You’d likely rally around them, listen, and offer support. Why do we assume others wouldn’t act as we would?

We can feel all the feelings and still learn. Failing hurts. But it’s the trying and learning parts that move us forward. It’s the courage that people take note of.

“Gosh, Caroline, it’s almost as if failure is a normal part of life.”

I wish people spent as much time bragging on their failures as they do with their successes. Those are the people I’m going to follow.

Read Part 2 - Looking Forward: 2021 Goals


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Author Bio: 

Before becoming a coach, Caroline worked in management consulting and financial services. She's made it her mission to help people grow, contribute, and get wherever they want to go.

She’s also a tennis fanatic, aspiring Minimalist, FIRE (Financial Independence and Retire Early) enthusiast, and Aloha Spirit seeker 🤙. She loves to share stories from her unconventional life and career focused on freedom, creativity, fun, health, family, and community. If she can do it, you can, too.

The life and career you want is possible once you have the roadmap. Take the first step by downloading your free guide: 4 Steps To Take Back Your Life and Design a Career With Purpose.


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