“I lost my job and I don’t know if I will be able to get one soon…”
These were the words my mentee shared with me three months ago.
His voice was shaking, confidence shattered, and future uncertain.
What happened next is why I’m passionate about mentorship.
Together, we took a step back to understand why he lost his position.
Not to place blame, but to identify growth opportunities.
We discovered patterns in his work approach that needed adjustment and skills that required strengthening.
Instead of rushing into the job search, we created a strategic development plan:
đ Upskilling in key technical areas
đ Rebuilding his professional narrative
đ Strengthening his network connections
đ Practicing difficult interview scenarios
The breakthrough didn’t happen overnight.
There were moments of doubt, rejection emails, and the inevitable “what if I never…” thoughts.
But last week, he called me with news that brought tears to my eyes:
“I just accepted an offer for a role that’s better than the one I lost.”
His success wasn’t just about landing a new jobâit was about the transformation in how he views his career, his resilience, and his potential.
This is why I mentor.
Because sometimes, what looks like a career disaster is actually the catalyst for someone’s greatest professional evolution.
Have you experienced a similar career setback that ultimately led to something better? Share your story below.
I Had to Say No to Mentoring Last Week.. I didn’t want to but…
Saying ânoâ isnât something I enjoyâespecially when it comes to mentoring. But last week, I had to do exactly that.
One of my mentees reached out, eager for a session. They wanted guidance on their next career move, some clarity on a tough decision. Normally, Iâd jump at the chance to help. But this time, I said no.
Not because I was too busy. Not because I didnât want to help. But because I realized that sometimes, stepping back is the best way to push someone forward.
This mentee had already asked me the same question multiple times in the past. And each time, I had given them detailed insights, frameworks, and action steps. Yet, instead of taking action, they kept coming back for more validation.
Thatâs when I recognized something: They werenât stuck because of a lack of knowledge. They were stuck because of a lack of action.
So instead of another conversation, I told them: âYou donât need more advice. You need to trust yourself and take the first step.â
It wasnât the answer they expected, but it was the answer they needed.
Mentorship isnât just about giving answersâitâs about knowing when to step back and let someone figure things out for themselves.
And sometimes, the most valuable lesson you can teach is that no one else can make the move for you.
Have you ever had to step back to truly help someone move forward?,
I wish I knew this before as a mentor…
The frameworks and systems we rely on as mentors are invaluable, but sometimes the most impactful guidance happens when we step beyond them.
Here’s how one mentoring experience transformed my approach:
My mentee had 8 years of experience but felt trapped.
Instead of jumping straight to career change, here’s what we did differently:
Started with a “Day in the Life” Exercise
- We mapped out his current workday, identifying moments when he felt most energized vs. drained.
- This revealed that he loved strategic problem-solving but was drowning in operational tasks.
Created a “Value Inventory”
- Rather than focusing on skills, we listed every instance where he’d created significant impact in his role.
- This uncovered his unique strengths: turning complex problems into actionable solutions.
Redesigned His Current Role Instead of leaving, we:
- Documented his high-impact contributions
- Created a proposal for role restructuring
- Identified projects aligned with his strengths
- Built a business case for delegation of operational tasks
Experimented with “Career Prototypes”
We tested small changes before big moves:
- Volunteered for strategic projects
- Shadowed roles he thought he wanted
- Took on advisory roles in other departments
The result?
He didn’t need a new career – he needed to reshape his current one.
By focusing on impact rather than titles, he negotiated a hybrid role that combined his expertise with his desired growth direction.
Key Learning:
- Sometimes what looks like career fatigue is actually role misalignment.
- Before making a complete switch, explore how to redesign your current position.
What I wish I knew earlier:
- The best career guidance isn’t always about plotting a new path – sometimes it’s about reimagining the current one.
Has anyone else discovered innovative ways to help mentees find fulfillment in their existing careers?
The tears in her eyes caught me off guard.
‘I feel like I’m letting everyone down,’ she whispered during our first goal-setting session.”
That vulnerable moment changed everything about how I approach mentorship.
It reminded me that behind every “professional challenge” lies a deeply personal journey.
Six months ago, I met a mentee who would transform my understanding of what it means to truly support someone’s growth.
On paper, she was brilliant – the kind of team member who could light up a room with her ideas.
But beneath that capable exterior was someone wrestling with the weight of undefined potential.
I still remember her nervously fidgeting with her notebook, trying to hide her frustration as we talked about quarterly objectives.
“Everyone else seems to get it,” she said, her voice barely steady.
“Why can’t I just figure this out?” My heart ached, recognizing that familiar dance of self-doubt.
It wasn’t the frameworks or templates that changed everything.
It was the day I shared my own story of struggling with goal-setting early in my career.
The relief in her eyes was immediate – like finally finding someone who spoke her language.
We laughed together about my own messy journey, and suddenly, the pressure valve released.
Magic happened when we stopped trying to fit her brilliant, creative mind into traditional boxes.
Instead of rigid structures, we created a vision board that looked more like an artist’s storyboard. Her entire energy shifted.
For the first time, I saw her shoulders relax and her eyes spark with possibility.
Nothing prepared me for the emotion of watching her present her first successfully completed project.
Her voice strong, hands steady, sharing not just results but the story of how she got there.
The pride in her smile mirrored the warmth in my chest – this was what true mentorship felt like.
What I’ve learned is that goal-setting isn’t just a professional skill –
- It’s an emotional journey.
- It’s about finding the courage to dream big while acknowledging our fears.
- It’s about building trust in ourselves and others.
- Most importantly, it’s about creating space for vulnerability in our professional lives.
đ To every leader reading this:
- When was the last time you let your guard down with your mentee?
- Sometimes, sharing our own struggles is the greatest gift we can give.
đ To every mentee:
- Your journey doesn’t have to look like anyone else’s.
- Your struggles don’t make you less capable – they make you human.
When has vulnerability in professional relationships led to unexpected breakthroughs?
“It’s 11 PM, and I’m staring at lines of code, realizing I want to be the one deciding what to build, not just how to build it.”
This was the message my mentee sent me 8 months ago, marking the beginning of an incredible journey from software development to product leadership.
When he first reached out, he was an exceptional software developer with 5 years of experience but felt something was missing.
He had the technical expertise but dreamed of shaping product strategy rather than just implementing it.
What followed was a transformative partnership that went far beyond just career advice.
Key Milestones in Our Journey:
1ď¸âŁ Foundation Building (Months 1-2):
- Mapped out gaps between development and product management
- Created a structured learning plan focusing on product strategy, user research, and business metrics
- Weekly deep-dives into real-world product cases, analyzing both successes and failures
2ď¸âŁ Skill Development (Months 3-5):
- Transitioned from writing code to writing PRDs (Product Requirements Documents)
- Practiced stakeholder management through role-play scenarios
- Developed frameworks for prioritization and decision-making
- Enhanced market analysis and competitive research capabilities
3ď¸âŁ Practical Application (Months 6-8):
- I connected him with product leaders in my network for informational interviews
- Conducted mock product presentations and interviews
- Built a portfolio of hypothetical product solutions
- Refined his unique value proposition as a technical PM
Just Last week, he called with exciting news – he’d landed his dream role!
But what truly moved me was when he shared how a framework we’d developed together helped him navigate a complex product challenge during his final interview. He didn’t just answer the question; he demonstrated the strategic thinking that sets exceptional PMs apart.
Key Learnings as a Mentor:
đ Technical expertise can be a unique advantage in product management when properly positioned
đ The best mentorship relationships are two-way streets of learning
đ Structured preparation beats sporadic advice every time
đ Confidence comes from repeated practice and constructive feedback
đ The transition from builder to strategic thinker requires patience and persistence
To aspiring mentors:
- The impact of mentorship extends far beyond career transitions.
- Every session taught me something new about leadership, challenged my assumptions, and helped me articulate knowledge I’d taken for granted.
- As he explored product management through fresh eyes, I rediscovered my own passion for the field.
Remember…
Every successful person you admire likely had a mentor who believed in them before success was guaranteed.
Who will you help write their next chapter?
“I’ve failed, Six months of work, and I couldn’t even get them to consider our proposal.”
This was my mentee!
Her presentation to the executive board hadn’t gone as planned, and I recognized that familiar look of disappointment â the same one I’d worn years ago before learning the power of gratitude.
Instead of jumping into problem-solving mode or offering immediate consolation, I reached into my drawer and pulled out a small, leather-bound notebook.
It was similar to the one my own mentor had given me years ago, a gift that had transformed my approach to both life and leadership.
“Tell me three things that went right today,” I said, sliding the notebook across my desk.
Sheh looked at me as if I’d suggested she could fly.
“Right? Nothing went right. The board…”
“Start small,” I encouraged.
“What happened before the presentation?”
Reluctantly, she began:
- “Well, the junior analysts stayed late last night to help me polish the numbers.”
- “The tech team fixed my laptop issues just in time.”
- “My team… they all came to support me, even though it wasn’t required.”
As she spoke, I saw the first glimmer of something shifting in her expression.
That’s the moment I knew she was ready for the real lesson â one that had taken me years to learn and now formed the cornerstone of my mentoring philosophy.
It wasn’t about ignoring problems; it was about approaching them from a foundation of strength and perspective.
I watched as her leadership style evolved.
The same determination that had once manifested as rigid perfectionism softened into resilient adaptability.
Her team meetings, once focused solely on targets and metrics, now included moments of recognition and celebration.
The change in team dynamics was remarkable â productivity increased naturally as people felt seen and appreciated.
Watching her transformation reminded me that gratitude isn’t just a personal practice â it’s a leadership tool that can reshape entire team cultures.
The greatest joy of mentorship isn’t in seeing your mentee succeed â though that’s certainly rewarding.
It’s in watching them discover their own path to joy and fulfillment, then passing those lessons on to others.
As mentors, we often think our role is to guide others toward success.
But what I’ve learned is that our real gift is showing them how to find joy in the journey.
Gratitude isn’t just a practice we teach; it’s the foundation that makes all other lessons possible.
When we teach gratitude, we’re not just developing better professionals; we’re nurturing more fulfilled human beings.
And isn’t that the greatest measure of success as a mentor?
Not too long ago, I spoke with a colleague who had recently transitioned into a leadership role.
On paper, everything seemed perfectâa significant promotion, a bigger team, and high expectations from the organization.
But during our conversation, she admitted something surprising: she felt completely overwhelmed.
The problem wasnât a lack of competence; she had always excelled in her previous roles. The challenge lay in transitioning from an Individual Contributor (IC) to a People Managerâa dilemma many professionals face at some point in their careers.
She found herself constantly questioning her decisions, wondering if she was spending too much time managing others and not enough doing the hands-on work she had always been great at.
This is where coaching made a world of difference for her.
Her coach didnât just offer generic adviceâthey helped her peel back the layers of self-doubt and uncertainty to uncover her true motivations.
Together, they worked to align her leadership style with her strengths and career aspirations, giving her the clarity she needed to embrace her new role with confidence.
This story highlights one of the five critical signs that indicate it might be time to seek coaching: the IC vs. People Manager dilemma.
Making this leap is about more than just new responsibilities; itâs about redefining your value, building new skills, and embracing a mindset shift.
Here are four other signs you might be ready to benefit from coaching:
1ď¸âŁ You Need an Outside-In Perspective
Feeling stuck in repetitive patterns?
A coach can help you see blind spots and uncover new possibilities.
2ď¸âŁ Maximum Effort, Minimum Results
Coaching can refine your approach for greater impact if youâre putting in the work but not seeing the outcomes.
3ď¸âŁ The Inspiration Tank is Running Low
Lost the spark that used to fuel your work?
A coach can help reignite your passion and realign your purpose.
4ď¸âŁ Navigating Role Transitions
Whether itâs a promotion, lateral move, or career pivot, a coach can help you thrive in unfamiliar territory.
Remember, seeking coaching isnât a sign of weaknessâitâs a bold step toward self-awareness and growth.
Have you ever faced a moment in your career where coaching could have helped? đ
Ps: I can guide/coach you through your journey.
âThe 2 AM Realization That Changed My Careerâ
Last night, one of my mentees shared a story that struck a chord with me.
She described a moment weâve all faced at some point: staring at her laptop at 2 a.m., not tired from overwork, but exhausted from monotony.
She said, âI realized I wasnât drained because I was doing too muchâI was drained because I wasnât doing enough of what truly excited me.â
Like many professionals, she had slipped into her comfort zoneâa good salary, a decent title, and predictable tasks.
But deep down, she knew something was missingâgrowth, challenge, and the spark that makes Mondays feel like opportunities, not obligations.
She recalled Milton Berle’s famous words: âIf opportunity doesnât knock, build a door.â Yet, like many of us, she stuck in the âplateau paradox.â
Comfortable enough to stay, but restless enough to know she needed change.
She started to recognize the signs:
- Projects that once excited her felt mundane.
- Her skills had stagnated.
- Team meetings felt like reruns.
And the dreaded phrase, âThatâs how weâve always done it,â echoed far too often.
When she reached out to me, she described feeling like she was lost without a map. Thatâs when I asked her to think of her career as a journey.
“Would you set out without a destination in mind?” I asked.
“If not, why let your career meander aimlessly?”
Together, we worked to redefine her goals.
She embraced the idea of her career as a growing vine, needing the right structure to climb.
She sought clarity and took bold steps:
- Enrolled in certifications to sharpen her skills.
- Shadowed leaders to gain fresh perspectives.
- Challenged herself with cross-functional projects.
Now, six months later, her career GPS has recalculated. Sheâs charted new routes, found exciting opportunities, and rediscovered her passion.
Her story is a powerful reminder: hitting a plateau isnât the problemâitâs what you do next that defines your growth.
Will you let it be a landing pad or a launching pad?
Whatâs your next move?