Sanity Check: Why Do We Keep Making the Same Career (and Life) Mistakes?
Definition of Insanity…
The Power of Reflection
Too often, we’re so focused on where we want to go that we forget to appreciate the journey. The milestones, the detours, even the flat tires — they all hold clues about what drives us and what holds us back. This blog invites you to take just a moment to pause, reflect, and create a roadmap for your future that’s rooted in understanding your past.
This isn’t about romanticizing “the good old days” or obsessing over past missteps. Instead, it’s about recognising patterns, identifying your true strengths, and finally letting go of the things that no longer serve you.
A Career Timeline: Your Personal Highlight Reel
Think of your career as a movie. There are scenes you’re proud of, moments you’d edit out, and plot twists that surprised even you. Now, let’s create your highlight reel:
Positions: List every role you’ve held. What did you love? What felt draining?
Teams: Who brought out the best in you, and who made you question your patience?
Feelings: How did you feel at each stage? Energized? Trapped? Excited? Burned out?
Money: While not the sole measure of success, how did each role align with your financial goals and values?
One of my clients, Sarah, started this exercise feeling unsure about her career trajectory. She’d spent years comparing herself to others and romanticising an old job she left long ago. But once we laid it all out — her roles, emotions, and outcomes — she realised that her “dream job” wasn’t so dreamy. The highs felt high only because the lows were unbearably low. The clarity was liberating.
The Relationship Parallel
This process isn’t limited to careers. It’s a game-changer for relationships, too. You know that ex you’ve been idealising? The one who sends you into a nostalgic spiral every time you hear that song? Write it out. The highs and the lows. When you see it in black and white, you’ll often find that the “good” wasn’t nearly as magical as your mind made it out to be. There were a lot more lows that made those high seem “higher” then reality… Perspective is everything.
Actionable Steps: Creating Your Career Map
Here’s how you can turn reflection into a powerful planning tool:
Create Your Timeline: Use a journal or a simple spreadsheet to list your career highlights and low points.
Spot the Patterns: Look for trends. Do you thrive in creative environments? Do structured roles sap your energy?
Define Your Non-Negotiables: Just like a future partner checklist, identify what you must have and what you absolutely won’t tolerate.
Visualize Your Future: With a clear understanding of your past, design your roadmap. What roles, industries, or projects align with your strengths and values?
What to Takeaway
As you glance in the rearview mirror of your career, you’re not just reminiscing. You’re recalibrating. You’re identifying the roads worth revisiting and the ones best left behind. Most importantly, you’re proving to yourself just how far you’ve come.
So the next time you feel stuck or uncertain, take a moment. Lay it all out. Your journey holds the answers you’ve been seeking. And when you’re ready to move forward, you’ll do so with a sense of purpose, clarity, and gratitude for the incredible road you’ve already travelled. Remember, the definition of insanity is repeating the same thing over and over and expecting a different result! So learn those lessons so that you can create new lessons for future you!
… Repeating the same thing and expecting a different result? Let’s pivot that today.