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4 Strategies to Master Your Midlife Career Transitions

career Apr 15, 2022
Diverse people holding up signs

There was a time when career paths were clearly defined. If lucky, you'd be hired on with a good company and progress to higher levels at the appropriate times. Ultimately, you'd retire having dedicated your prime years to the company. Unfortunately, those days have long disappeared. It's no longer about company loyalty but loyalty to self-interests. The last two generations of employees have focused on better compensation and job satisfaction. At the same time, employers have focused their attention on operating lean, productive, and efficient machines.

Today, on average, a person will change careers 5-7 times during their working life. The average person will change jobs about 10-15 times within those career shifts. Between downsizing, outsourcing, telecommuting, and the entrepreneurial boom, our once clear career paths have become more like career mazes.

You may be on your second career and investigating a third if you're reading this. You're perfectly normal.

In Jon Acuff's book, Do Over, he talks about the four reasons we may find ourselves in a career transition. As a result of one of the above rationales, you may have experienced one of the following in your career:

  • Jump - a chosen career transition
  • Bump - an involuntary change due to a layoff or firing
  • Ceiling - where you've reached the height of your current career ladder
  • Opportunity - where an unexpected new position has emerged

To master these various transitions, you must accumulate career capital in the form of business contacts, technical skills, character, and gumption. Together, the combined wealth of this career currency will support you in achieving your desired results. However, each transition requires an abundance of one over the others.

I will use one of my favorite movies to further demonstrate these transitions.

Career Jumps

Working Girl is a classic movie that turned 30 this year. While it's woefully outdated in several ways, some great lessons can still be learned.

I have nostalgia for this movie because I worked in the Financial District on "Chicago's Wall Street" in sales, wearing my shoulder pads and sneakers to work, dreaming of my career trajectory in the late 1980s. I left a position as a retail supervisor because I longed for a job with an office and a view. But unfortunately, my dreams were dashed when I found myself working for my own version of Katharine Parker.

Like Tess, I decided to make a career jump. I thought about becoming a lawyer for several years, and my current situation gave me the motivation I needed to make the leap.

To successfully go through a career jump, however, you must have a strength of character. It's scary learning to navigate new terrain when fear and self-doubt are your constant companions. Know who you are and rely on the strength of your convictions that are pointing you in the direction you need to go. Tess "jumped" from secretary to financial executive, and it took a belief in her abilities to step into Katharine's shoes.

Whenever you start something new, you may feel like you're back at the novice level. For a seasoned professional, this can be pretty uncomfortable. However, if you approach the new role with open-mindedness, like a hungry newbie, you'll see you know more than you know while also finding new and creative ways of doing the work and advancing your current skill level.

Career Bumps

When you go through a career bump, and Tess went through a couple of times in the movie, it's essential to cash in on the career capital of business contacts.

Katharine once told Tess, “Never burn bridges. Today’s junior prick is tomorrow’s senior partner.” She was absolutely correct. Your business relationships won't all become close personal relationships, and that's ok. Building good business contacts will be helpful when you find yourself unexpectedly out of work. Let your network know when you're available for new opportunities and specifically what you're looking for.

Whether you need an informational interview, mentor, or a job, reach out to those connections you developed so they can access their network on your behalf.

Career Ceilings

Career ceilings occur when you reach the top of a career ladder or hold a position that no longer maximizes your skills and abilities.

When you hit the ceiling, it's time to gain additional skills, knowledge, education, or experience to position yourself for what's next. Tess reached her "ceiling" as a secretary, so she honed her skills over time in various positions and added to her knowledge by receiving a business degree with honors. She said, "I read a lot of things. You never know where the big ideas could come from." 

Up-leveling your skills will support your next move and prepare you for those career opportunities that may come your way.

Career Opportunities

We don't often get the opportunity to go from secretary to financial executive overnight; or get offered a new job while literally walking out of another as Tess did, but that's what career opportunities are all about.

When an opportunity presents itself, how do you react? You can see your next best steps before they present themselves when you have true vision clarity. In fact, you work to put yourself in opportunities way.

Tess captured it when she said, "I’m not going to spend the rest of my life working my ass off and getting nowhere just because I followed rules that I had nothing to do with setting up." Opportunities call for gumption. Whether you call it gumption, chutzpah, or hustle, the key is to be agile and ready to take advantage of the right opportunity for you.

Without gumption, you'll miss out. Instead, you'll be left with doubt, confusion, and fear, unsure about what to do when your best opportunities arise.

A Word About Your Brand

When going through various career transitions, you must consider your personal brand. It's critical to update or entirely revamp your brand to stay current and prepared for what's next.

Personal branding is about impression management. Like it or not, your clothes speak. What you wear influences how you feel about yourself and how others perceive you. Quoting Coco Chanel, Katharine told Tess, “Dress shabbily, and they notice the dress. Dress impeccably, and they notice the woman.”  Picking up on this, Tess shifted her appearance from wild and trendy to sophisticated and classic. Hey, “You wanna be taken seriously, you need serious hair.”

If you're in transition, take a moment to evaluate your visual brand and make the necessary adjustments. Your visual brand should give you the confidence to leverage your career capital.


I've made a few career transitions over my working life to appreciate the importance of career capital. In hindsight, I can also see the importance of having someone who can help you gain the clarity you need to navigate the career maze. It's no longer a straight line to where you want to go and what you want to do. I'm grateful for the twists and turns in my career because it's made me a better coach and consultant, and it has informed my life's work.

I'm confident it was the combination of investing in relationships, advancing my skills, gaining character, a lot of gumption, and a kick-ass personal brand.

Would you like support mastering your career capital to support your transitions? Let's connect today!


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