How Your Best Lessons Can Become Your Biggest Obstacles
Beginners Mind Can Help
When I was a little girl, I remember adults talking about "emotional baggage." Imagining a heavy suitcase, I wondered, "Why don't they just put it down and move on?" As an adult, I now understand how difficult that can be. Hard-earned lessons and battle scars from life, relationships, and difficult situations become deeply ingrained in our way of seeing and interacting with the world, making it hard for us to notice them, much less set them aside. This can be just as problematic at work.
Last week, I was chatting with a CMO who was expressing her frustration that her hard-earned lessons weren't helpful in each new company, and several were actually working against her. The mistakes she’d learned to avoid, the things she wanted to do right next time, weren’t even on this playing field. The goalposts had moved. Different CEO, different culture, different market moment, different challenges.
I could empathize. When I ran awareness advertising for Oracle, success meant learning every preference of Larry Ellison's and quickly aligning everyone across every global touchpoint with his decisions. Although Atlassian's CEOs initially sought my Oracle experience, it was quickly apparent that success at Atlassian was about appeasing the democracy, bringing everyone along: navigating the differing opinions of, at the time, two CEOs, a president, and three general managers, and testing many ideas instead of dominating with one big bet. Many patterns and recommendations from my previous jobs were no longer relevant as we developed new ways of doing things. I had trouble context switching and had to quickly retrain myself to do things at Atlassian that would have been abominable at Oracle. It was hard.
I frequently encounter this in my advisory business. Executives who were rewarded for thrifty, measured growth needing to experiment in bold ways with budget bets to drive faster growth. Or big company executives who found success hiring and delegating needing to get deep in the weeds with their smaller-company teams. Or CMOs who ultimately found success with a micromanaging CEOs feeling uncomfortable and distant from their new, completely hands-off CEO.
In each new company and role, we face challenges big and small. We build playbooks, we build scar tissue, we form operating principles. And while so often new companies tell us they are hiring us for our experience and perspective, it often needs to get checked at the door.
As I commiserated with this CMO on the challenges of navigating our corporate emotional baggage, I mentioned that “We must enter again with a beginner's mind.”
When we got off the phone, I looked up the tenets of beginner’s mind (or "Shoshin" in Zen Buddhism). It encompasses several key concepts:
Openness and Curiosity - Approaching situations without preconceived notions about how things "should" work. Instead of assuming you know the answer, you remain genuinely curious about possibilities you haven't considered.
Freedom from Expert's Bias - As the famous Zen saying goes: "In the beginner's mind there are many possibilities, but in the expert's mind there are few." Expertise can create blind spots and rigid thinking patterns that prevent us from seeing new solutions.
Present-Moment Awareness - Focusing on what's actually happening now rather than filtering everything through past experiences or future expectations. This allows you to respond to current reality rather than to your memories or assumptions.
Non-Attachment to Outcomes - Being willing to let go of how you think things should unfold and remaining open to unexpected results or approaches.
Intellectual Humility - Acknowledging that you don't know everything and being comfortable with uncertainty. This creates space for learning and growth.
Fresh Perspective - Seeing familiar situations as if encountering them for the first time, which can reveal insights that experience-based assumptions might obscure.
These principles were helpful reminders. The most successful CMOs I know operate with a deep confidence in their ability to learn and adapt, paired with genuine curiosity about what will work in each new context. They treat their past successes as data points, not rules. They ask more questions in their first 90 days than they answer. And they don’t overuse “At my last company we…”
This adaptive mindset isn't just about professional success - it's about professional survival. The marketing landscape is changing too quickly, and companies vary too widely, for most of our playbooks to work time and again. The CMOs who thrive are the ones who've made peace with constantly reconstructing their approach.
So if you're feeling frustrated that your hard-earned lessons aren't translating, or that you're having to "unlearn" things that served you well before, you're not alone. It’s not that easy to put down those heavy suitcases of experience. Your experience matters. But your willingness to adapt it, challenge it, and sometimes set it aside entirely is required on this wild ride.
Carilu Dietrich is a former CMO, most notably the head of marketing who took Atlassian public. She currently advises CEOs and CMOs of high-growth tech companies. Carilu helps leaders operationalize the chaos of scale, see around corners, and improve marketing and company performance.
Loved this read and spot on. Not attaching from outcomes when you are wired for impact is hard, but I'm learning there is impact in the journey and process if you focus on that and not a defined outcome.