The ‘Second Half’ of Your Career: Less about you, more about others

Depending on where you are in your career, you’ve probably started to realize that your career journey isn’t a very linear path. There tends to be quite a few twists, turns, and sometimes complete 180-degree pivots, and guess what: it’s all normal. Careers can be organized in two big chunks: first half and second half. Each “half” has its own challenges and rewards, and each requires you to be adaptable.

Denise Hutton, a business executive specializing in HR and a 4word mentor, talks about how the beginning of her career set up the “second half” she’s currently in, and shares the 10-year blocks most careers can be broken down into.


Tell us a little about yourself!

I am a wife, mother and leader. I am blessed to have married my best friend, Mark, and my greatest accomplishment is my family, including my two amazing boys.

I am a servant leader who values connection, a learner who believes in staying curious, and an executive who values change. I am a business executive who happens to specialize in HR. My passion is helping leaders unlock their purpose and potential. I love building strong, purpose-driven organizations that deliver exceptional results!

In my spare time, you will find me outside hiking, kayaking, or in our hay field on the farm surrounded by one of my American Eskimo dogs. 

My personal motto: Work Hard, Stay Humble, Find Purposeful Work.

How would you define the “second half” of a career?

The “back half,” as my mentor calls it, can happen at different milestones for everyone, but as a general rule, it is the point of your career when you’ve shifted from exploring and developing functional expertise and are beginning to teach and invest in the next generation of those coming behind you. 

I’ve heard the seasons of a career defined in 10-year blocks:

What are some unique challenges someone can expect in the second half of her career? Are there some unique opportunities?

I’ve found that many women in high stress roles hit the “wall” as they begin the transition into the back half of their careers. Oftentimes, they’ve spent many years building a career and they now find themselves not as fulfilled as they once were or thought they would be once they got “there.” That wall occurs at a different place for all of us, but a common question that signals its approach is, “Is all this worth it?”  

That question can be scary if you come at it from a place of regret instead of curiosity and gratefulness. Remember: all that the Lord has prepared you for has brought you to this particular moment in your career. 

I did executive coaching for women in this career season and it was remarkable how consistent the questioning was with many of them. Everyone was on a different journey, but they each were questioning the things they used to hold of great importance. Why, at what was supposed to be the highlight of their careers, did they feel so unfulfilled? They wanted to know that all the effort was worth it, that it mattered. Exploring these questions is what helps people emerge with focus, passion, and grit to tackle the next season of their careers.

How have you navigated the second half of your career? How did it differ from the first half?

I’m not as fearful of adversity in my career as I once was. I’ve gotten on the other side of enough seasons of unemployment, toxic teammates, and horrible bosses and found that it didn’t matter if the outcome was what I thought it should be, or not. The Lord is gracious and has something for me to learn through it. Early in my career, I spent so much energy on trying to “fix” the problem instead of pausing to ask the Lord, “What are you teaching me through this?”

My identity is not as wrapped up in the position I hold. A year of unemployment was the blessing that revealed to me how much of my identity was connected to my work. When I didn’t have work, who was I? 

The gift of that year was clarity and I now find myself making career decisions that are driven by my sense of purpose instead of a specific position. I’m grateful for the incredible leaders and opportunities I’ve had over my career, but now I’m much more thoughtful about the potential “next role” and think of my career as a lattice to explore versus a ladder to get somewhere. 

What advice would you offer to someone about to start the second half of their career? What are some valuable lessons you’ve learned along the way?

Lean into the season and use the questions that might be coming up for you as an opportunity to get clear on what the Lord is calling you toward for this season. Sometimes the Lord calls us into and out of careers.

Reevaluate your goals. Is what you are working towards aligned to where/what you feel the Lord calling you? You should have different goals in your “second half” than you did in your first half of your career.

Don’t be afraid to make a career pivot. I believe that oftentimes, our greatest calling is on the other side of some of our greatest fears.

Companies are realizing that needed skills and capabilities can shift quickly (COVID-19 taught us this!) and what they really need are employees who demonstrate learning agility. I am seeing this become a much higher priority than traditional functional skills. If you are feeling led to a career shift, how might you apply your learnings thus far in your career to this new opportunity?

Anything else you’d like to share?

Seek out someone who is at a career stage behind you; invest in them, offer your mentorship. Looking back and helping someone else through a season you’ve already walked can reveal quite a bit about how you might look forward to the future.


With over 20 years’ experience in executive roles across Learning Development, Talent Management, Sales, Service and Operations, Denise Hutton understands what it takes to drive both business operations and strong cultural performance. She was Vice President of Learning and Organizational Development for a $5B retail technology company and held Vice President roles in Customer Experience Strategy and Sales & Service Operations for international companies.

Denise takes pride in developing others and leading teams who are engaged and inspired to serve customers. She is a leader with a successful track record of building organizations that improve the customer experience and operational performance. With a blend of strategy and execution she is gifted in translating the “why” into the “how” – leveraging insights into action. She is a respected thought leader within the Learning & Talent Management community with a strategic mind, strong leadership aptitude and the ability to identify, design and implement practical solutions which drive large-scale change. She holds a Bachelor’s Degree in Business Administration from Cardinal Stritch University and has credentials in executive coaching and  instructional design. Her leadership development programs have been featured at the Robert Greenleaf Institute for Servant Leadership, Skillsoft, Executive Learning Exchange and Argyle Forums.