Your Career Rearview Mirror – Learning From the Bumps in the Road

They say that experience is the best teacher, but only the lessons are bought dearly. As managers, our careers are full of ups and downs, victories and setbacks, smart moves and regrettable blunders. The journey is rarely a smooth highway – it’s more like a winding backroad with potholes, detours, and blind curves at every turn. 

The most successful managers are not those who have flawless careers without a single misstep. Rather, they are the ones who are able to reflect deeply on their experiences, both positive and negative, and extract valuable insights to apply going forward. Just as a skilled driver uses their rearview mirror to navigate safely, an effective manager must continuously look back on where they’ve been in order to chart the best path ahead.

Over my 25 years in leadership roles across various industries, I’ve had my share of accomplishments and failures. Each peak and valley has been an opportunity for growth if I took the time to stop, take a deep breath, and consciously learn from that experience. It’s a practice I’m still honing, but one that has been absolutely essential to my own professional development.

If you’re ready to start mining the gold from your career journey – the good, the bad, and the ugly – here are five techniques to try:

1. The Quarterly Reflection

This simple but powerful exercise involves scheduled reflection every 3 months. Block off 2-3 hours of uninterrupted time, either at home or an offsite location. Leave your devices behind and bring only a paper notebook.

Start by reviewing your calendar and emails for the past quarter to resurface major events, meetings, and situations. What were the highs and lows? The accomplishments and dropped balls? Jot down a chronological list spanning the highlights and lowlights. 

Next, select 3-5 of the most significant experiences, both positive and negative. Spend 20-30 minutes free-writing on each one, digging into not just what happened, but how you felt, how you responded, what you might do differently next time, and what lessons you can extract. 

The final step is to review all of your notes and synthesise your top 3 takeaways from the quarter. Write out an action plan for how you will apply these lessons over the next 3 months.

2. The Restart Interview

Based on a practice from researchers at Yale University (Ibarra, 2003), the Restart Interview involves imagining yourself at the start of your career again with the opportunity for a fresh start. With that freedom, who would you want to be? What paths would you want to take?

Sit down with a trusted friend, family member, or mentor. Have them ask you a series of powerful questions to spark self-reflection:

“Imagine it’s 20 years ago and you’re just beginning your professional journey. What advice would you give your younger self?”

“What’s the smallest change you could have made early on that would have put you on a better path?”

“What’s one interest, passion, or opportunity that you let slip away? And why?”

Dig deep, be honest with yourself, and write down the responses that resonate most with you. Are there inflection points you missed? Risks you didn’t take? Parts of yourself you suppressed?  

The exercise allows you to reimagine and reclaim the areas where you may have strayed from your most authentic path. Use those insights to course-correct in your current reality.

3. The Anti-Resume

We’re all familiar with resumes that market our skills and accomplishments. But what about shining a light on our shortcomings and failures? The Anti-Resume does just that in a powerfully vulnerable way.

On one side of a paper, craft a traditional resume highlighting your career achievements thus far. On the other side, create an “Anti-Resume” – a chronological list of your biggest professional mistakes, failures, fired jobs, and learning experiences.

For each Anti-Resume item, ask yourself:

– What went wrong and what was my role in it?

– What did I learn from this experience that has made me better?

– How has this helped me course-correct professionally?

The Anti-Resume is the ultimate humility exercise. It forces you to confront your insecurities, admit your flaws, and find the growth opportunities within your failures. Review it often as a reminder of how far you’ve come.

4. The Odyssey Map

We tend to think of our careers as a linear progression – Start at Company A, work up to Manager, jump to Company B for a Director role, and so on. But in reality, our paths are rarely so simple and straightforward. They zigzag and loop back through unexpected detours.

The Odyssey Map is a visual depiction of your entire career journey to this point. Either draw it by hand or use online mapping tools. Plot each job, role, industry, location, and transition as a series of stops along your personal Odyssey. 

Don’t just focus on the paid roles. Include volunteer work, sabbaticals, job searches, gaps in employment, passion projects, and any other meaningful experiences. For each stop, note down a few words capturing the key lessons, skills, or impacts from that particular chapter.

Once fully mapped out, spend some time analysing where your journey has taken you and what has shaped you most. Look for the pivotal forks where you made difficult choices. See if you can spot any full-circle moments or re-emerging threads. And importantly, recognise the roadblocks that may have sent you down detours – those are often the biggest teachers.

5. The Mentor Journey

We tend to consider mentorship as a one-way relationship – the protégé gleaning wisdom from the been-there-done-that mentor. But the truth is, those mentor relationships can be just as insightful and impactful for the mentor.

Make a list of every individual you’ve mentored during your career to date – direct reports, university students, company program participants, community mentees, etc. For each person, reflect anon:

– What was this individual’s unique ambition, challenge or area for growth?

– How did my own experience allow me to guide or advise them?

– What did I learn about myself through our interactions?

– How did this mentorship shape or evolve my own management philosophy?

Too often, we undervalue the growth that can occur through the act of mentorship. But these relationships not only impact the mentee, they also shed light on our own strengths, weaknesses, and blind spots as managers. Learn from the mirror they’ve held up.

No matter which of these techniques you try, the critical step is taking the time to stop, pause, and reflect intentionally. Left unexamined, the ups and downs of your career can simply feel like a crazy rollercoaster ride. 

But when you commit to extracting the lessons from each loop and drop, you give meaning to the journey itself. You start to connect the dots and see how each experience has been builder knowledge, wisdom, and decision-making skills. Like a great coach who studies game films, you’ll start recognising your own patterns – what causes you to stumble as well as what unlocks your highest performance.

The path ahead may still have twists and turns, but you’ll be a more self-aware driver able to navigate with confidence. So use that career rearview mirror, learn from the bumps, and mark a few potholes to avoid next time. The journey is never as important as where it leaves you.