27 September 2023

Failing safe: How to remove the fear of failure

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Kathy Caprino* has some advice for people who find themselves stuck in a job or career they hate, but who worry that any change will make things even worse.


When I was in my most unhappy period at the end of my 18-year corporate career, I was the definition of ‘stuck’.

At age 40, I had spent all those years slogging through jobs and promotions, trying so hard to finally land a senior role that I could love and feel I was great at.

I desperately wanted to be a part of a company that was delivering products and services that made me feel I was doing something meaningful with my time.

It just wasn’t happening.

Worse than that, I was chronically ill, exhausted and extremely isolated and burnt out.

The core problem was I was clueless as to what else I could for a living that would earn what I and my family needed and not require me to start completely over.

Nothing I pursued in the way of help offered a concrete solution or a new direction.

I had already worked so hard that I didn’t want to make a huge mistake and fail big again.

I did the worst thing anyone can do if they want to change careers or pivot to a new direction — I did absolutely nothing.

I didn’t network or explore new avenues; I didn’t talk to inspiring people; I didn’t attend conferences or workshops that would teach new skills.

I didn’t even accept a great new job that was offered to me because I worried it might be more of the same.

Progress just doesn’t work that way.

Nothing will change if you wait until you think you know exactly what you want to do before you take any steps.

Success won’t come at all if you’re so desperately afraid of failing that you won’t even consider exploring a new direction.

Instead, you have to begin to get moving now, and start taking brave, empowered micro-steps that will open new doors for you.

It’s in the execution of these brave (and often intimidating) steps that will guarantee you will grow in the confidence and self-esteem you need to make a change.

If you’re unhappy in your career but have absolutely no idea what else you could do that would earn good money, here are three steps that you can take right now.

First, start recognising what you’re drawn to outside your job.

Explore how you can apply your existing skills to a new direction that has the same ‘essence’ as this thing you love

Let’s say you’re a sales director for a telecommunications company and you’re really good at and enjoy sales, but can’t stand working for a telco.

Let’s say too that you’ve always loved international travel and every chance you get, you’re off exploring distant cultures and lands.

Think about how you can potentially shift to a new sales role that is focused on selling or promoting cultural or international experiences.

Where can I leverage what I already know and do well, but in a new direction that I’m passionate about?

Start talking to anyone you can think of who might have some good ideas for you or contacts to explore how you can continue doing what you’re great at, but pivot to a new direction.

Second, if you want a completely new career, narrow down three directions that you’d like to explore.

Most professionals who want to chuck their careers completely have no idea what they would do instead.

That keeps them locked in paralysis.

Take a step back and identify fields you’ve always been interested in since you were young.

Identify what you really value, enjoy and cherish in life.

Brainstorm a full list of your skills and capabilities and research new career directions that need these skills.

Explore what it would take to get more training and experience in these exciting fields.

Talk to 10 professionals who are engaged in these fields, to get a real-world perspective of what’s involved.

Take a long, hard look at your finances, and wherever possible, do what’s necessary to build some savings for a ‘career growth fund’.

Narrow down three possible directions you want to learn more about, and connect with people on LinkedIn and in your personal network who are doing this work.

Get their feedback.

Finally, get an accountability buddy for this process.

You can’t create an amazing career alone.

You need inspiring and empowered people in your life to help you stay motivated, energised and engaged in the process of growth.

An accountability buddy, mentor or supporter can help you develop a concrete plan for exploring and trying on a new career or a pivot that will make you happier.

It takes time and commitment, but one thing is certain: If you don’t get on the path to exploration, nothing will ever change for you.

Who do you know that might be a great mentor or coaching buddy?

Reach out to a few good friends or colleagues who love what they’re doing professionally and have taken brave steps to get there.

Share what you’re hoping to do, and ask if they might be open to providing some ongoing mentorship for you.

*Kathy Caprino runs a leadership and career coaching and consulting firm for women. A therapist and coach, she has worked with more than 10,000 emerging women leaders and can be contacted at kathycaprino.com.

This article first appeared on Kathy’s blogsite.

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