5 Career Decisions That Can Backfire and Crush Your Success

Part of Kathy Caprino's series “Finding Brave to Build Your Best Life and Career”

Before I mustered the bravery to reinvent my career from unhappy corporate VP to career coach, writer and speaker, I was stuck in a corporate marketing career that was just plain wrong on so many levels. While it was “successful” on the outside (meaning, I made good money, had high-level responsibility, earned lots of perks and benefits, oversaw large projects, etc.), it was a train wreck from an emotional perspective.

Looking back on those 18 years of corporate life, I see now that my real talents and abilities – the ones that make me feel alive and of value and use to others – weren’t being tapped at all. Because of that, I often felt the success I achieved never delivered the impact or satisfaction I wanted. The work and outcomes I focused on in my corporate jobs rarely matched the real me or aligned with my truest values and ideals.

According to a recent Gallup study, global employee engagement overall is now declining again. Following a steady rise over the last decade, employee engagement decreased globally by two percentage points, from 22% in 2019 to 20% in 2020. That means a full 80% of employees are NOT engaged in their work. Clearly, leaders need to take different kinds of actions to address this decrease and its negative business impact on workplace culture, employee retention and performance.

Back in my corporate career, I felt disengaged in my work, and found very little meaning or constructive purpose in this career I’d worked so hard to build. Despite all the “sensible” decisions I made in managing my career, I ended up shattered and lost at 41.

What kept me stuck in this career pain and dissatisfaction? It amounted to a series of critical career choices and decisions that I believed made sense and were wise to make at the time, but in the end, they completely failed me. And the core mistake I made, over and over, was not recognizing that what we are most naturally gifted and talented at doing – what comes easily and joyfully to us – are the same talents we should be leveraging in our careers, instead of focusing on skills that are deeply challenging or demotivating to use. Further, if the outcomes we’re focused on in our work don’t honor our core values and ideals, we’ll suffer.

Working with hundreds of professionals each year, I’ve seen that there are 5 career decisions and choices people make that often backfire, and lead to failed careers and painful outcomes. 

Over 95% of the professionals who come to my firm for career help are making at least one of these mistakes, and on average they’re making three of these at the same time.

These errors in decision-making around our career choices destroy great opportunities, and slam the door on career happiness and true, heart-aligned success.

These 5 critical career decisions that fail us are:

Going only for the “safest” thing

Understandably, professionals want something safe and secure for their careers and profession. The problem is, nothing today is really “safe and secure” (as we've seen once again this past year) except the talents you possess inside of you and your commitment to using and growing them. Entire industries and fields can evaporate quickly, or morph into new directions. Many professionals over 45 whom I've worked with have stopped refreshing and updating their knowledge base and skill set and are finding that they’re being viewed as obsolete, replaced by younger professionals who have their finger on the pulse of the new innovations and directions in their fields.

For more on this, check out my Finding Brave podcast interview with Fawn Germer, about How to Win the Job You Want When You've Lost the Job You Need:

Midlife professionals sometimes admit that they simply can’t keep up with the pace that’s demanded of them, but they feel it’s too late to make a change. It’s too risky, too unknown, too scary, to make a significant shift. And they're afraid of all the money they believe they'll lose. So they stay in what they think is safe only to find that staying safe was about the most unsafe thing they could do.

Tip:  Stop worrying about safe. The only safe thing is growing yourself, and making great use of all that you know to help others.

What is the scariest thing you’ve been wishing you could do? Seriously evaluate what it would take to do that scary thing, or some version of it, that could make you great money but also honor what you know to be true about yourself and who you want to be in the world.

Not fully leveraging your deepest, most needed talents

What many corporate professionals fail to understand is that each of us possesses great natural talents and abilities that the world needs, and that organizations must have to thrive. The key is to identify those talents within you (they’re often not readily apparent to you because you’re so naturally good at them), and learn to apply those in new ways that are needed by organizations or others to help them grow.

Tip: Many people can’t even answer the question “What are you great at?” If you can't answer that question, then you can't speak compellingly about your talents either, and that leaves money, opportunities and advancement on the table.

If that’s you, take the time now to identify your true, natural talents that have been with you since your teen years. Think about how these talents have helped organizations, teams and people grow and thrive. What outcomes were you able to achieve that others couldn't have, because of what you do and what you know. Then determine how you can now leverage these talents more powerfully to make a difference in new roles that you’ll find juicy and rewarding. (Take my free Career Path Self-Assessment to gain greater awareness of what you're truly great at.)

Not pivoting to a new direction that “connects the dots” AND addresses the changes in the market

I’m a big fan of doing work that elicits passion in you, because passion keeps your work fresh and new, and motivates you to continue to find new ways to leverage that stream of energy and commitment for exciting outcomes.

Where passion goes wrong for people is that they think that’s all they need to be successful, and that’s not accurate. And it goes wrong when people refuse to see that the world has changed and they can't be successful the way they used to go about it. They need to pivot.

For instance, I know so many musicians, artists and creatives who can no longer earn what they need to because the business and financial model for the arts has dramatically shifted. Yet they refuse to apply their artistic talents in other ways that would generate income.

Here's a firsthand account, from Grammy-nominated composer and orchestrator Jeremy Levy, at how a very talented artist pivoted to use his creative gifts in new ways to great success:

The type of “pivot” I'm referring to is a change in direction that honors everything you’ve learned and know, but also allows you to direct your energies in more satisfying ways where your skills are most needed.

For example, after my corporate life I became a marriage and family therapist. While I loved every minute of the learning and training required to become a therapist, and it was a life-altering experience, I ended up not enjoying or thriving in the professional identity of serving as a therapist – the day-to-day realities and requirements of a working therapist. But my dissatisfaction as a therapist pushed me to pivot to a new identity I love – serving as a career and leadership coach, writer and educator. 

This role allows me to utilize all that I’ve learned as a therapist, but also draw on my corporate experience, and my experiences as a manager, performer and writer. And running my own business gives me the chance to utilize the expertise I gained from my corporate marketing, research, management and product development roles. 

When done correctly, a pivot can bring out all of you, and nothing is wasted.

Tip: Explore and “try on" in risk-free ways 5 different potential directions that will allow you to pivot so that you can use everything you know, but leverage it in a new direction that will generate what you need and want.

Not recognizing that you have to think of yourself as more than just one job or title

I hear from hundreds of professionals who’ve been in one job for many years, and that’s all they think they are. They’ve been disengaged from the world outside. They haven’t been involved in the essential aspects of networking we need, or utilizing LinkedIn and other social platforms to build their profile or community.

They haven’t connected to colleagues outside their company. They’ve stayed small, hiding. They haven’t attended conferences or industry association meetings. They haven’t learned anything new. They believe that all they are is their current job. In short, they know only their limited role and function, and haven’t expanded beyond that or their organization. I call this "Power Gap #4: Isolating from Influential Support," one of the 7 most damaging power gaps that 98% of professional women face today.

Tip: If you’re reading this post, you most likely want to significantly revise your career. Take the time this week and month to begin to stretch yourself far beyond your one role and employer. It’s a big, beautiful world out of there of amazing people doing inspiring things, sharing enlivening ideas. Join that bigger world.

Start reaching out to former colleagues on LinkedIn, and build your personal brand there. Give endorsements and testimonials, update your resume, contact recruiters, and reach out to 10 new people a week and make a new connection. Change your LinkedIn profile headline so it's not just about this one job you have - it's about all that you are and have been in the workforce. Start talking about what you’d like to do next, and ask for help, even if your ideas about what you want to do aren’t fully baked yet.

Remember, you are so much more than this one job or function.

Not committing to stretching yourself farther

Finally, there is one career decision that’s sure to lead to failure – it’s deciding NOT to grow and expand your skills set because you think you’re fine where you are. I’m working with two mid-level clients right now who did this – they admittedly failed to stretch, grow and learn more or refine their skills. They didn’t make use of tuition reimbursement at their jobs and take additional courses they needed to build cutting-edge skills.

They knew they had power gaps (and even what I call "dirty little secrets") in their current role or from their past and couldn’t perform at the top level, but wouldn’t address those gaps. They chose not to accept an exciting new project in a different department because they were either scared they’d fail, or didn’t think they “needed” to engage in this new direction. And they refused to look for another job until they were forced out of their current one.

Tip: You simply can’t achieve the success and impact you long for if you don’t commit to growing. Stretching out of your comfort zone (which for many people has lost any feeling of "comfort") isn’t just a nice thing to do. It’s vital to success, happiness and growth. Determine three ways today that you can start growing and learning something new, and get moving to stretch beyond who you think you are today.

For more career growth support, visit KathyCaprino.com, her Finding Brave podcast, and work with her in a Career Breakthrough program. And check out her latest book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss, and the upcoming digital companion course, The Most Powerful You.