Learning from My Biggest Career Regrets

U Turn Dirt Road WildernessCelebrating a milestone birthday recently has brought with it reflection, perspective and a slice or two of humble pie. So as I begin my 6th decade (I’ll let you do the math), I’d like to share some things I’d do differently if I were starting my career over again.

1. Find what I love to do and do it – sooner.

Thankfully, I am in a great career that I love. But it took me a while to get here. I began my career in systems design, corporate finance and HR process and program design roles. These roles played to my business, strategic thinking and analysis bents, and I learned much from the experiences. But nine years of liking my jobs 20-30% of the time was probably seven years too long.

Once I shifted to a career focus I loved – for me it’s been moving to roles where people development was my “major” rather than a “minor” – I’ve liked my job 70-80% of the time. And this has made all the difference. Lesson learned: life is too short and work takes too much time NOT to go after jobs that we love when we have the opportunity.

2. Don’t avoid politics.

I remember one headline from my first performance review: “Joe, you do great work but you need to promote yourself more.” At the time, I dismissed the feedback; it ran counter to personal values I had that involved being humble and letting my work speak for itself versus tooting my own horn. Years later, I was passed over for a promotion and wound up working for a peer who was more politically astute than I was. Through this experience, I learned the hard way how naïve and self-righteous I had been.

There is a way to maintain integrity while learning to operate in the “political savvy zone.” Looking back, I wish I would have learned this earlier in my career – not only for my own career advancement – but in order for me and my teams to have greater influence, impact and effectiveness.

3. Take more risk.

I’m a calculated risk-taker. But sometimes I calculate too much. Because I tend to look before I leap, I have avoided some serious mistakes. But I have also gotten stuck or delayed in analysis paralysis. Making a decision often involves risk and requires guts and faith; we rarely have all the data or certainty we want.

Speaking up with an unpopular opinion. Making a needed career change. Initiating a difficult conversation. Trying something outside your comfort zone. Pulling the trigger to begin a strategic initiative. Or leading others through a change. For any of these, there is only so much looking you can do before it’s time to leap. (See a great article in HBR from my colleague @PattiBJohnson if you, like me, find managing uncertainty challenging.)

Do you have career regrets? The good news about acknowledging regrets or failures is that lessons learned from them can benefit you and others. Whether your career regrets involve finding work you love, being politically savvy, taking more risk or something else, may you turn regrets into wisdom from lessons learned.

Joe Baker is a Partner with PeopleResults. As a leadership consultant and executive coach, he helps leaders and their teams learn and improve from their own and others’ successes and mistakes. You can reach him at jbaker@people-results.com or on Twitter @JoeBakerJr.