Stuck in a Career Rut? How Successful Men Overcome Midlife Dissatisfaction
Do you feel a sense of dread creeping in as Sunday evening winds down and Monday looms ahead? While your role was once exciting and engaging, it has now become repetitive tasks and petty politics. If you’re experiencing this, you’re not alone. Many successful men in midlife encounter this precise career plateau. Though disorienting, the good news is that it’s relatively common and consider it your (sometimes unwelcome) invitation to a more meaningful next chapter.
Understanding Your Career Plateau
Research from economists David Blanchflower and Andrew Oswald highlights a powerful insight:
Life and work satisfaction typically follow a U-shaped curve, dipping to their lowest in your 40s before rising again.
While not exactly a rite of passage for everyone, it’s also not a sign that you have made the wrong choices or are simply ungrateful. It simply tells you it’s time for some adjustments.
Several factors often contribute to this plateau:
Changing personal values: Our first decades in true careers (as opposed to just jobs) usually involve trying to ensure that we are progressing in our career, getting to financial security and earning our status. As we get established and settle into our roles we shift our values wanting much more meaning, autonomy and contribution.
Repetitive challenges: Experience means you have the wisdom to know how to handle things That usually comes from doing the same things enough times. In some circumstances that can get repetitive and stagnant as your learning curve flattens dramatically.
The Golden handcuffs: Our lifestyles tend to grow with our incomes. Financial comfort can trap you in roles you no longer enjoy, amplifying the fear of leaving stability behind.
Misalignment with leadership: The company’s vision might no longer align with your personal values, turning even a good job into a burden. This can happen because of the arrival of a new leader or simply realizing that you have changed and you don’t feel like you can get behind where the senior leadership team has identified.
I’ve faced my own career plateau. Despite an amazing leadership team I built and continue to invest in their growth, there came a moment when I realized my personal growth and deeper satisfaction lay elsewhere. It took me about ten months of strategic planning and quiet preparation to transition confidently. Ensuring I had laid the appropriate groundwork to create something to shift into as well as the right runways to support the in between time. Ultimately, leaving opened new paths I couldn’t have imagined.
Recognizing Signs of Career Dissatisfaction
Do these resonate with you?
– You dread Mondays more intensely each week or too much of your year centres around a few precious vacation weeks?
– You’re increasingly disconnected from your leadership’s vision.
– You know that you aren’t engaged at work but also feel trapped in the financial security waiting around for a particular event or date years in the future.
– You’re struggling with a feeling of restlessness, despite your outward success. You minimize the boredom by reminding yourself how many people aspire to be in a role like yours.
If these ring true, your discomfort isn’t just an inconvenience — it’s a sign you’re ready for growth.
Facing Fear of Change
Change can feel overwhelming, especially at midlife. Common fears include:
– Financial insecurity: “What if I can’t replicate my current income?”
– Fear of judgment: “What will people think if I walk away?”
– Loss of identity: “Who am I without my professional title?”
– Feeling outdated: The thought of marketing yourself or switching industries feels overwhelming after years of stability.
It means accepting that change usually requires some discomfort but letting fear make the decision for you leaves you trapped in a place of unhappiness and will continue to rob you of energy and inspiration every day.
“The cave you fear to enter holds the treasure you seek.”
Joseph Campbell
If your work life feels misaligned but you’re not sure what’s next, the Midlife Clarity Self-Assessment can help.
This free, thoughtfully designed workbook helps you uncover what’s working, what’s not, and where to go from here.
Practical Steps to Reignite Career Satisfaction
Here are concrete strategies that can ease your transition and reignite your passion:
1. Conduct a skills and passion audit
Take inventory of your skills and passions to pinpoint what excites you now. Your skills have a market value and knowing what type of work energizes you helps match you to the best future opportunities.
2. Run Small Experiments
Don’t quit impulsively. Instead, try out new career options through side projects, freelancing, or networking events. This doesn’t have to be all or nothing. Give yourself the time and space but keep moving forward.
3. Create a Transition Plan
Financial concerns are valid. Plan your financial runway, engage in strategic networking, and thoroughly research new opportunities before you move.
4. Adjust Your Mindset
Rather than radical reinvention, think of this as refining your existing skills and experiences to match your evolving goals and interests.
Reignite Your Career Satisfaction
If you’re experiencing midlife dissatisfaction, take heart — this period of restlessness is your opportunity to redefine your career, reignite your passion, and realign your life with your true values.
You’ve achieved so much. Now it’s time to intentionally design the next stage of your life.
Brendan Abbott blends sharp strategic insight with emotional depth — providing a confidential, judgment-free space to discuss anything. From career pivots to addressing deeper personal truths. He acts as a guide, coach, and confidential advisor.
