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Things to Remember as You Move Through Your Career

Today’s Tuesday Reading is from Kerry Flynn, newly retired as CIO at the Ross School of Business at the University of Michigan, and a MOR alum, sharing career advice for IT leaders. Kerry may be reached at [email protected] or via LinkedIn.

As I prepared to retire, one question came up again and again: “What are you going to do?”

Quite frankly, I had no idea. After spending more than 45 hours a week working for over 36 years, I hadn’t spent much time thinking about what would come next. People often seemed disappointed when I answered, “I don’t know. I’ll figure it out.” I would explain that I had lists upon lists of things I wanted to do, read, experience, and cook. When I was ready, I would simply start working my way through them. I was comfortable with the idea of being flexible and letting retirement unfold naturally. 

As my retirement date approached, many members of my staff also asked me for advice, feedback, and suggestions for their careers and professional development. While there are countless lessons to share after a long career filled with learning and change, three pieces of advice stand out as particularly important. 

1. Leadership Is a Practice, Not an Inborn Trait

You are not born a leader. Leadership is a skill that must be continually practiced, developed, and refined. How you practice depends on your individual strengths and areas for growth. That ongoing commitment is what keeps a leader effective, relevant, and adaptable. 

Once we become comfortable in our roles and understand our jobs and the environment around us, it can be tempting to coast. I believe great leaders recognize when they reach that point and make a conscious choice: either move on from their positions or challenge themselves to keep growing and practicing leadership. 

I had a teacher who used to say, “Study on a regular, daily basis.” I believe the same principle applies to leadership. It requires consistent, intentional practice. 

Choose one leadership skill each week and make it a goal to practice it. It might be the Four I’s, providing meaningful feedback, improving communication, or strengthening another leadership skill. Whatever you choose, be deliberate about putting it into practice. Leadership development doesn’t stop when you get the job or earn the title. That is when the real work begins. 

2. Keep Humor Front and Center 

When I talk about humor, I don’t mean that everyone needs to be a comedian. Humor simply has a way of lightening the moment, easing stress, and diffusing tension in a difficult meeting or challenging situation. 

In IT, we often deal with system outages, critical incidents, and situations where the stakes are high. When something goes wrong, it can feel as though we need to be serious at all times to demonstrate that we understand the severity of the situation and are working hard to resolve it. 

Of course, resolving the issue quickly and effectively is critical. But being serious about the problem doesn’t mean we have to be serious every second of the process. 

Too often, team members feel they must maintain a solemn demeanor to prove they are taking the situation seriously – and they are. But a little humor, a well-timed joke, or a moment of levity can relieve tension and help everyone regain perspective. 

As a team member or leader, you can acknowledge the seriousness of a situation while still creating an environment where people can breathe, think clearly, and work together. Humor doesn’t diminish the importance of the work; it can make the work more manageable and the team more resilient. 

3. None of Us Are Perfect, So Stop Taking Yourself So Seriously 

We spend years climbing the ladder, working toward the next position, promotion, or salary increase. Along the way, we often develop an idea of what success looks like – and sometimes, we convince ourselves that if we do everything perfectly, we will be recognized, promoted, or move on to the next opportunity on our list. 

But careers rarely unfold exactly as planned, and perfection is an unrealistic standard to hold ourselves to. At the end of the day, all we can do is our best. Mistakes will happen, plans will change, and sometimes things won’t turn out the way we hoped. It means we’re human. 

There is a reason people say that perfection is the enemy of good. When we focus too much on getting everything exactly right, we can lose sight of what we’ve accomplished, what we’ve learned, and the value we’ve contributed along the way. 

So, give yourself a break. Celebrate the wins, learn from the setbacks, and remember that your career is a journey, not a checklist of positions to achieve. You’ll enjoy that journey a whole lot more when you allow yourself to be human along the way.

Which of Kerry’s lessons resonates most with you?

Last week, we asked about the most meaningful action you could take in the next week to increase the return on your experiences.

  • 50% said I have something else in mind.
  • 34% said establish greater accountability.
  • 7% said contact a colleague for candid perspective.
  • 5% said revisit a framework connected to a current challenge.
  • 4% said reflect on a recent experience and adjust.

The importance of accountability and follow-up resonated from last week’s reading. This is such a foundation to applying tools and frameworks in a meaningful and beneficial way. What resonated even more was making your experience your own. Finding those ideas that meaningfully resonate for you and being intentional in leveraging them.

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