Designing a Career That Holds You
Reflections from a Black Sherpa 29k Club Masterclass with Jeffrey Boakye — Author, Educator and Cultural Commentator
Why Your Experiences, Values and Perspective Matter More Than You Think
“Your opinions sit at the front of your lived experiences.”
“Your career is an ongoing design process.”
“What are you working on?”
Sometimes a session lands differently.
You can feel it happening.
The chat becomes more active.
People unmute themselves.
Laughter breaks the tension.
Someone pauses and says something that makes the room stop for a second.
That was the energy during our recent Black Sherpa 29k Club masterclass with Jeffrey Boakye… educator, author, cultural commentator and one of the most thoughtful voices exploring identity, culture and education today.
Jeffrey didn’t arrive with a corporate framework or a polished “five steps to success.”
Instead, he invited us into something far more powerful.
A conversation about:
perspective
identity
curiosity
and the quiet insights we gather as we move through our careers
Because the truth is, most professionals are walking around with valuable insight… but very few have been taught how to recognise it.
Three Cups and a Room That Came Alive
Early in the session Jeffrey showed a simple slide.
Three cups:
a red mug
a wooden tumbler
a white disposable plastic cup
Then he asked a question.
“Which one would you choose?”
Immediately the room woke up.
People began explaining their choices.
One participant liked the red mug because it matched the mug they already owned.
Another preferred the wooden cup because it felt more sustainable.
Someone chose the plastic cup because it was simple and practical.
The conversation became animated.
People laughed.
Someone jokingly reacted with mock horror when the plastic cup was chosen.
It was playful.
But Jeffrey pointed out something deeper.
None of these opinions were random.
Every preference came from lived experience.
What you’ve done.
What you’ve learned.
What you care about.
What you’ve been taught to value.
That’s where your perspective comes from.
And the same principle applies to your career.
Your Career Is a Design Problem
One of the most powerful ideas Jeffrey introduced was that careers are not simply discovered… they are designed.
Think about the cups again.
Everyone is a one-of-one design classic
They all serve the same purpose: holding liquid.
But each one has been designed differently.
One works better for hot drinks.
One prioritises sustainability.
One is cheap, disposable and practical.
None of them are objectively “better.”
They are designed for different needs.
Jeffrey encouraged the group to think about their careers in the same way.
Most people enter industries without asking the design questions:
What kind of environment allows me to thrive?
What does this career actually need to hold?
What values do I want reflected in my work?
Instead, we often inherit systems that evolved around assumptions about how careers should look and who typically progressed through them.
As workplaces become more diverse, more professionals are discovering that some of those structures don’t always fit the realities of today’s workforce.
Which means careers sometimes require redesign.
The Four Spaces We All Move Between
At one point Jeffrey introduced a framework that helped people think about their relationship with work.
He asked participants to choose their favourite and least favourite spaces from four options:
Gym
Stage
Home
Workshop
Each represents a different way we experience our professional lives.
Growth happens across four spaces: where you train, where you think, where you share, and where you build
The Gym
Work as training.
The gym is where you test yourself, push limits and build strength through effort.
Many careers start here… learning the craft, building resilience and developing confidence.
The Stage
Work as performance.
The stage is where we present a version of ourselves to the world.
Think:
presentations
meetings
conferences
professional profiles
As Jeffrey joked during the session, our professional profiles often show the most polished version of ourselves.
The stage matters… but it is still a performance.
Home
Work as belonging.
Home is where we feel comfortable being ourselves.
Some workplaces create this environment.
Others are still learning how.
The deeper leadership question becomes:
how do we create cultures where people feel safe enough to show up fully?
The Workshop
Work as experimentation.
The workshop is where things go wrong.
Where ideas are tested.
Where prototypes fail.
Where insights emerge.
And according to Jeffrey, this is where the most important learning happens.
But many professionals avoid the workshop.
Because experimentation requires vulnerability.
The Question That Changes Everything
Throughout the session Jeffrey returned to one simple question:
“What are you working on?”
Not:
What’s your job title?
What’s your next promotion?
What’s your five-year plan?
But:
What are you working on?
When Jeffrey managed teachers earlier in his career, he asked them two questions during every review:
What’s going well?
What are you working on?
The first builds confidence.
The second creates direction.
Because if someone knows what they’re working on, they’re already growing.
Without that clarity, people drift.
Identity Isn’t Just Personal… It’s Professional
Another powerful part of the session explored how identity shapes professional experience.
Jeffrey invited the group to think about the labels that shape who we are.
Name.
Nationality.
Gender.
Race.
Sexuality.
Background.
Profession.
Each element influences how we move through institutions and systems.
Experiencing the edges of systems can be difficult and frustrating.
But it can also create a vantage point… allowing people to see patterns and dynamics that those closer to the centre sometimes miss.
In other words:
perspective often grows from experience.
And the insights that come from those experiences can become incredibly valuable when they are shared.
The Golden Triangle of Professional Impact
Jeffrey also introduced a framework he uses when teaching.
In education he describes a triangle made up of:
The student
The teacher
The text
Each element matters equally.
But the triangle is surrounded by context.
Context includes:
culture
technology
politics
economics
inequality
social change
He then translated this framework for professionals.
In most industries the triangle becomes:
The client or end user
You
Your expertise
And once again everything sits inside context.
Many professionals focus only on the expertise corner.
But the most effective leaders understand all three:
Who they serve
What they know
How the wider world is shaping the work
Ignore context and strategy quickly becomes outdated.
Your career isn’t a ladder to climb… it’s a design process shaped by your experiences, values, and perspective
Your Winning Strategy
Towards the end of the session Jeffrey shared a story from childhood.
“Someone saw the potential early... I’ve been trying to live up to that report ever since“
He showed a school report describing him as:
talented
hardworking
well behaved
“one of the nicest children I’ve ever taught”
The room laughed.
But Jeffrey explained something important.
This wasn’t accidental.
Growing up as the child of immigrants on a South London estate, he realised early on that his winning strategy was simple:
Work hard. Be perfect. Don’t cause trouble.
Many high-performing professionals develop similar strategies early in life… especially when they feel they need to prove themselves.
Those strategies often work.
But every strategy has a shadow.
For some professionals that strategy becomes:
perfectionism
people-pleasing
overworking
avoiding conflict
The behaviours that once helped someone succeed can eventually become limiting.
Which is why understanding your winning strategy matters.
Because once you see it clearly, you can decide whether it still serves you.
Enthusiasm and Meaning
At another moment in the session Jeffrey explained the origin of the word enthusiasm.
It comes from the Greek word entheos, often translated as inspired or filled with spirit.
When someone is enthusiastic about something, it feels like they carry something bigger than themselves.
This is why people are drawn to individuals who speak with conviction.
Not because they are perfect.
But because their work connects to meaning.
Key Lessons from the Masterclass
Some of the most practical takeaways included:
Your experiences shape your perspective
Every opinion you hold comes from what you’ve lived through.
Careers are designed, not discovered
Ask better questions about what you want your work to hold.
Treat work like a workshop
Experimentation and failure are sources of insight.
Capture your insights
The moments that make you pause often contain valuable learning.
Ask yourself what you’re working on
Growth requires direction.
Your identity can be a source of perspective
Experiences that challenge you can also sharpen your insight.
Your winning strategy deserves reflection
What helped you succeed early on may not always serve your future.
Meaning fuels enthusiasm
People are drawn to work that connects to purpose.
Why This Conversation Matters
When organisations ignore these dynamics, the consequences are real.
Talented professionals begin to:
feel disconnected from their work
question their value
hide parts of themselves
or quietly disengage
Innovation slows.
Trust erodes.
And organisations lose the very insight they need to evolve.
Leaders who create environments where people can reflect, experiment and share insight unlock learning that no training programme can manufacture.
The Black Sherpa 29k Club Difference
Conversations like this are exactly why The Black Sherpa 29k Club was created.
Many talented professionals… particularly those from underrepresented backgrounds… are navigating workplaces that feel confusing or opaque.
They are capable.
They are ambitious.
But they often lack three things:
Clarity about how systems really work
Confidence to trust their own voice
Community to share experiences with others on similar journeys
The 29k Club exists to create those spaces.
Spaces where people can reflect on their experiences, challenge assumptions and turn insight into action.
Because when professionals learn from each other, the climb becomes clearer.
As Jeffrey put it during the session:
“No one tells you that when you enter a profession, one of your biggest responsibilities is to interrogate it.”
About the Speaker
Jeffrey Boakye is an award-winning author, educator, and cultural commentator known for turning complex ideas about identity, education, and culture into clear, thought-provoking insights.
A former teacher, Jeffrey is the author of acclaimed books including Black, Listed, Musical Truth, and I Heard What You Said, and regularly speaks and writes about culture, language, education, and lived experience.
In this 29k Club session, Jeffrey shared a powerful question he asks in every review conversation:
“What are you working on?”
A simple shift that moves the focus away from job titles and towards direction, growth, and impact.
Connect with Jeffrey
Website: jeffreyboakye.com
Instagram: @jeffreyboakye
LinkedIn: Jeffrey Boakye
A Final Leadership Challenge
Before you move on, take a moment to reflect.
Ask yourself:
What am I currently working on… really?
What experiences are shaping how I see my sector right now?
What insight have I gained that others might benefit from hearing?
Your career is not just a path.
It’s a design process.
And every experience you’ve had so far is part of the blueprint.
Climb steady 🖤
I’m Yam – Founder of The Black Sherpa
Founder | Strategist | Speaker | Host of The Black Sherpa Podcast
I founded The Black Sherpa to create a world where talent rises on merit and no one’s potential is held back by bias or barriers.
Through bold strategy, storytelling, and our flagship community, The 29k Club - I help professionals grow with confidence and support leaders to build cultures that truly live their values.
Let’s connect and build a future where inclusion powers performance, and leadership reflects the world we serve.