The Regret Reset: How Midlife Women Can Transform Regrets Into Career Clarity
Ladies, let's talk about something that's been keeping way too many brilliant midlife women awake at 3 AM: regrets.
You know the ones I'm talking about. Those persistent "If only" thoughts that whisper (or sometimes shout) in your ear:
"If only I'd gotten my MBA when my company offered to pay for it..."
"If only I'd learned social media marketing when it was emerging..."
"If only I'd built a stronger financial foundation so I'd have more freedom now..."
"If only I'd been braver and started my own business ten years ago..."
Sound familiar? If you're nodding your head right now, you're in excellent company. These regrets are showing up in my coaching practice constantly, and here's what I've discovered that's going to completely shift your perspective:
Your regrets aren't evidence that you've failed. They're actually your secret career compass in disguise.
Why Midlife Women and Regrets Go Hand in Hand
Here's what I know to be true: having career regrets at midlife isn't a sign that you've messed up your life. Not even close! It's actually proof that you've lived long enough to develop the wisdom to know the difference between what you thought you should want and what you actually need to thrive.
Your 25-year-old self made career decisions based on what she thought would make everyone else happy - stability, prestige, fitting in, checking all the "right" boxes. But your midlife self? She gets to make decisions based on what you now KNOW lights you up from the inside out: meaning, purpose, authentic expression of who you really are.
And here's the beautiful plot twist: this wisdom you've gained through experience? It's your competitive advantage, not your setback.
The Four Types of Regrets That Are Actually Gifts
Based on Daniel Pink's research in The Power of Regret, there are four main categories of regrets - and I'm absolutely fascinated by how these show up for midlife women specifically. Over the next several weeks, I'll be diving deep into each one during my Morning 20 LinkedIn series, but let me give you a preview of why each type is actually pointing you toward something powerful:
Foundation Regrets: "If Only I'd Built a Better Base"
These are the regrets about things you wish you'd done to set yourself up for success - degrees, certifications, financial cushions, different early career choices. But here's what I see in my coaching practice: women who obsess over their "missing" MBA often overlook the incredible experience and wisdom they've gained through years of real-world leadership.
Boldness Regrets: "If Only I'd Been Braver"
These sting the most because they're about chances not taken and playing it safe when your soul was calling you to leap. But these regrets are actually revealing your deep desire for authentic expression and meaningful impact.
Moral Regrets: "If Only I'd Done What Felt Right to Me"
These are about times when you compromised your values or didn't stand up for what you believed in. These regrets are your internal moral compass recalibrating and showing you exactly what matters most to you now.
Connection Regrets: "If Only I'd Prioritized the Relationships That Really Mattered”
These are about the personal relationships that got overlooked while climbing the corporate ladder - missing family moments, letting friendships fade, or not nurturing the connections that feed your soul. For many Gen X women, these regrets reveal how the pressure to "have it all" often meant sacrificing the relationships that actually sustain us. But these regrets are pointing you toward something beautiful: a desire for deeper authenticity in all your relationships, both personal and professional.
The Regret Reset Mindset: From Paralysis to Power
Here's where it gets exciting, ladies. Instead of using these regrets as evidence that it's "too late" for you, what if we used them as the GPS system for your next career chapter?
Every single regret is pointing you toward something you value deeply. If you regret not getting that MBA, it's because education and growth matter to you. If you regret not being bolder, it's because authentic expression and meaningful impact are calling to you. If you regret compromising your values, it's because integrity is non-negotiable for you now.
Your regrets are the tuition you paid for this incredible wisdom.
Why Midlife Women Have the Advantage
You have something those bright-eyed younger colleagues don't have: clarity that only comes from decades of real-world experience. You know what drains your soul and what fills your cup. You know which environments bring out your absolute best and which situations make you feel like you're shrinking instead of growing.
This isn't about having it all figured out at 25 - you weren't supposed to! You were supposed to live, learn, grow, and arrive at THIS moment with the clarity to create a career that feels like home. This aligns with research from Harvard Business Review showing that while satisfaction may dip in our 40s, it typically rebounds stronger than ever in later years.
Your Regret Reset Action Plan
Over the next month, I'll be taking you through my complete Regret Reset framework during my Morning 20 series on LinkedIn, but here's how you can start shifting your relationship with regrets right now:
Step 1: Inventory Your "If Only's" Write down every career-related regret that comes to mind. Don't judge them - just acknowledge them.
Step 2: Find the Values For each regret, ask yourself: "What does this regret tell me about what I value?" If you regret not being bolder, boldness and authentic expression matter to you. If you regret not building stronger relationships, connection and collaboration are important to you.
Step 3: Look for Patterns What themes emerge? Are most of your regrets about not taking action (boldness)? Not preparing enough (foundation)? Not staying true to yourself (moral)? Not prioritizing certain relationships(connection)?
Step 4: Use Regrets as Your Roadmap Instead of evidence of failure, treat your regrets as a roadmap for your next career chapter. What do they tell you about the kind of work environment, role, or career path that would feel authentic to you now?
The Beautiful Truth About Starting Over at Midlife
Here's what lights me up about working with midlife women: when you finally stop apologizing for not having it all figured out earlier and start using your regrets as wisdom, everything shifts. Your posture changes, your energy lifts, and career clarity starts flowing naturally.
I've seen women in their 50s launch successful consulting businesses using skills they thought were "just part of their old job." I've watched women in their 40s pivot into completely new fields because they finally gave themselves permission to follow what energized them rather than what they thought they "should" do. And the data backs this up! Research shows that millions of people successfully change careers at midlife, with most reporting greater happiness as a result.
Your regrets aren't evidence that you're behind. They're evidence that you're ready to build something meaningful.
What's Coming Next
This is just the beginning of our Regret Reset journey together. Over the next several weeks during my Morning 20 series, we'll dive deep into each type of regret and how to transform them into your career advantages:
Foundation Regrets: How to build your launch pad without having to boil the ocean
Boldness Regrets: Why your "missed" opportunities are actually pointing you toward your next brave move
Moral Regrets: How to use your values as your career north star
Connection Regrets: Building the relationships that support your wellbeing and authentic self
Click here to follow me on LinkedIn and join my Morning 20 series!
Your Next Step
What career regret are you ready to reframe as wisdom gained? What "If only" has been haunting you that might actually be pointing you toward your next chapter?
Remember, those regrets you're carrying aren't mistakes - they're the tuition you paid for this incredible wisdom. And now it's time to put that wisdom to work creating a career that feels like home.
Ready to stop letting regrets hold you back? Take my FREE Career Alignment Assessment and discover how to use your "If Only" moments as the foundation for your dream career.
I’m Dawn LaRae, The Midlife Career Whisperer™! I help midlife women design their dream career so they can experience passion and purpose in their work.
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