Leadership – Craig Jamieson

Startups, You Don’t Need a CDO Yet

I was recently approached to take on a Chief Design Officer role for a startup. Pre-anything. Equity stake, interesting project, no compensation until the first round of funding. All reasonable asks given the requirements were minimal.

I will not get into the specifics of why I did not jump at the opportunity, but I will say this: they do not need a CDO.

Most early stage startups do not. Not even scale-ups until there is a larger set of resources in place who truly need that level of leadership. Sure, you can bring one in fractionally, but the work founders think a CDO should be doing is rarely the work of a CDO.

Yes, we carry years of wisdom, but you also need someone on the tools. Most CDOs are more than capable, but why disrespect them by asking them to do the job of a mid-level designer? That is not the work of a CDO. I have yet to meet a seasoned CTO who is expected to sit and code full time.

This is a role that is simply not required at the early stage. When you are bootstrapping, making promises you cannot guarantee, bringing in a CDO is not the solution.

The better opportunity is for a senior designer. Someone 5–10 years into their career. Someone who is comfortable wearing multiple hats, who can handle the hands-on work to ship an MVP and secure funding. Get a CTO and a CDO to advise if you like, but do not rope them in with a title and then expect them to do work they have not done in a decade.

I hear a lot about ICs, but even most of them are overly qualified unless this is just a side project they are passionate about. They deserve more respect than being used as a stop-gap. The role of a CDO is to lead the function, not just push the pixels.

That is not arrogance. I still jump in Figma. I still design every day. But my role has a better use of time. My value is in setting vision, representing the function, and scaling design so that it has the impact it should.

When you hire a CDO you get years of experience in navigating complexity, shaping organisations, building systems, and ensuring design serves the business at scale. You also get recognition given to the team, responsibility taken for the outcome, and a leader who knows the details without having to do every detail themselves.

I worked hard to reach this level, as have many others. It is not about being above the work, it is about applying hard-earned experience for the right impact.

A Chief Design Officer is not what an early stage startup needs. At that point, you need hands-on design, not design leadership. Bring in someone who can wear many hats, move fast, and get you to an MVP. Save the CDO role for when you are ready to scale design into a function that drives the business forward.

Respect the role. Respect the people. Put them where they can create the most value.

In Good Company

There are a few companies I wouldn’t mind working for. Some because they’re innovative, some out of curiosity, and others because I use them regularly and know I could help make them better. I admire the craft, the clarity, and the culture some have built. They’re real places where I believe I could add real value. My career has taught me that the best opportunities often come from unexpected places. Every role sharpens your instincts, strengthens your systems thinking and makes you a better designer.

Lego

Anyone who knows me knows I build Lego. I don’t want to be a set designer or a master builder, that’s my hobby. What I’d love to do is help elevate their digital experience. From the website to in-store journeys, there’s room to build more cohesion and consistency. With the right structure and creative leadership, their experience could feel as satisfying and smart as the product itself.

Grab

When I lived in Thailand, Grab became my go-to for everything. Rides, food, groceries, cleaning, you name it. It’s probably the most-used app I’ve ever had. The core product is powerful, but the experience can feel disjointed. I’d focus on bringing unity across services, sharpening the flow, and simplifying support. It’s a product I respect and use, and one I know I could make even better.

Amazon

Most of my experiences with Amazon have been difficult. I still can’t access my account, and the interface is hard to navigate. I use it often in design audits as an example of how inconsistency adds up over time. That’s exactly why I’d love to work there. I’d bring leadership, structure and clarity to a platform that millions rely on. This one is all about the challenge.

Apple

I use the ecosystem every day and it works the way I work. It supports, syncs and connects without friction. I also admire their willingness to take risks and stay the course. Their design team is one of the few that still moves with purpose. I’d love to be part of that environment and contribute to the next wave of experiences inside a system that values both restraint and innovation.

Porsche

I’ve grown to really appreciate Porsche. Not just for the product, but the precision of the brand. From language to visuals to touchpoints, everything feels thought through. That kind of consistency doesn’t happen by accident. I’d be proud to help maintain and extend that strength across digital products and future-facing platforms.

Red Bull

I don’t drink energy drinks, but I love what Red Bull has built. The strategy, the brand worlds, the culture around it, it’s an incredible ecosystem. The content, placement and community are on a different level. I’d love to build experiences that bring those stories to life digitally, with the same energy and originality they bring to everything else.

Liquid Death

It’s just water, but the way they’ve branded and built around it is clever. The tone, the packaging and the attitude all cut through. It’s not my typical style, but I respect how clear and bold they are. I’d like to help them grow without losing that edge.

Revolut, Wise, Monzo

These fintech platforms are part of my daily life. I use Wise the most, Monzo is polished and easy to use, but Revolut stands out in terms of potential. Their growth is impressive and their features are genuinely useful, but the experience could be sharper. I’d bring clarity, consistency and structure to help any of them move faster and more confidently. It’s a space I know well, and where I could contribute from day one.

Teenage Engineering

Their products make you feel something. The aesthetic is strong, the thinking is clear, and the connection between form and function is rare. They remind me of what Dieter Rams might be building today. I’d love to contribute to shaping the next digital layer of their ecosystem. Products like these deserve experiences that feel as considered as the design itself.

Formula 1

I’ve always liked the racing, but it’s the data, overlays and live interaction that I find fascinating. The way they present complex information clearly, and bring it into the broadcast experience, is world class. As F1 evolves into more than a sport, I see massive opportunity to contribute to the lifestyle, media and technology experiences around it.

A24

Everything they release feels crafted. The films are distinctive, bold and filled with creative details. I’d love to build immersive digital experiences around their sci-fi and genre pieces. Interfaces that fit the world, not just the film. There’s huge opportunity to create something original and meaningful in this space.

LV

Luxury is expanding its audience. Brands like Louis Vuitton are showing up in culture, sport and tech, not just fashion. The physical side is refined, but the digital side still has room to grow. I’d love to help elevate that. Something that feels like Moleskins Timepage, useful, elegant, clear. That level of product design is where I’d add value.

Tesla and SpaceX

I’d work on any of Elon’s companies, including X. The challenges are clear and I have ideas. I’ve already prototyped voice interfaces for Tesla, and know someone working on the rocket UI for SpaceX. These are spaces where traditional interface thinking doesn’t apply. That excites me. I’d give everything to help shape these experiences, because they’re not about browsers or phones, they’re about future interaction.

Gymshark

I train every day, and I respect how Gymshark built their brand from the ground up. I don’t wear their gear, but I know their story, and I admire their approach. The connection with athletes like CBUM is strong, and their community is massive. I’d love to help shape the digital tools and platforms that connect it all.

Dyson

Whether people love or challenge their products, I admire how design-led the company is. Dyson solves real-world problems across hardware, health and home, and does it with ambition. I’d move to Singapore if I had to, but the UK base also appeals to me. I’d bring creative leadership, system thinking and experience design to a company that experiments with purpose.

There are a few agencies I’d be happy to work with too, but that’s a conversation for another time. I’m not trying to build my own thing. I want to lead a creative team inside a company. That’s where I do my best work.

Which company would you want to work for?

Considering Fractional Leadership

Over the past few years, the market has shifted in ways that have forced many of us in executive creative roles to rethink how we work. The budgets that once supported full-time Chief Creative Officers or Chief Design Officers are harder to justify, especially for smaller or scaling businesses. This reality has prompted me to explore new ways to apply my experience and leadership without requiring a full-time executive headcount.

One option I have been considering is stepping into a fractional leadership role. In this arrangement, I would serve as the CCO or CDO of a business that needs senior guidance but is not in a place to bring on an executive permanently. The idea is simple: dedicate a predictable amount of time each month to the company and its teams, delivering strategic direction, supporting execution, and coaching internal talent. For example, this might look like two hours every day, which could cover team catch-ups, creative reviews, leadership discussions, workshops, or client meetings.

While that sounds like a lot of meetings, if time is structured thoughtfully, it becomes surprisingly manageable. The time allocation does not have to be a strict daily schedule. Some days could require only an hour, while others might need three. Some weeks could be lighter. The important thing is that there is a clear monthly commitment that everyone respects. As the business grows and the value of the role becomes more apparent, the hours can scale accordingly.

This is not an ideal substitute for a fully embedded executive. Building genuine relationships and understanding the nuances of a company’s culture and processes takes time that is hard to compress. However, when both sides are committed and communicate openly, it is possible to create an arrangement that delivers real impact.

To be effective as a fractional leader, you need to manage multiple clients at once, which requires discipline, transparency, and mature boundaries. It is essential to have regular check-ins with company leadership to confirm that expectations are met, to highlight any gaps you see, and to request additional time when deeper consideration is needed. Without that trust and clarity, the model will struggle to deliver value.

Despite the challenges, I believe fractional leadership holds promise. For companies under pressure to reduce fixed costs while still needing strategic creative guidance, it can be a practical solution. It can also be a more flexible way for experienced leaders to share their expertise across multiple organisations that otherwise might never have access to that level of support.

If you run a business or lead a team, I would be interested to hear whether this approach resonates with you. Could a fractional CCO or CDO help your company grow without the full cost of a permanent executive? Feel free to share your thoughts. This is an evolving idea, and the conversation is worth having.

The True Weight of Creative Leadership

Today, I read something from a creative outlier I deeply respect, who essentially stated, ‘In the age of AI, you’re all creative directors now,’ reducing the role to merely telling others what to do without doing the actual work. It hit a nerve. That has never been my experience, not by choice, anyway.

Delegation isn’t about avoiding work. It’s about maximising your impact by entrusting your team with responsibilities and not undermining them by doing their tasks when things go off track. It’s trusting them, nudging them, and ultimately becoming a ‘genius maker.’

But leadership is far more than delegation. It comes with great power, and as the Spider-Man comics remind us, ‘With great power, there must also come great responsibility,’ a phrase coined by Stan Lee. As I reflected on my journey, it became clear to me how much more there is to leadership.

You Own the Vision
You set the course for your team and projects. You must constantly ensure everyone stays aligned, reimagining that vision again and again as landscapes shift and challenges emerge. It’s not a one-time thing you delegate to someone else. It’s an ongoing responsibility that sits squarely on your shoulders.

You’re Responsible for Careers
The work your team produces shapes their professional identity. Poor quality leaves them with little to showcase and excellence sets them on an upward trajectory. When they move on, the standards you set become benchmarks for their future roles, influencing their careers long after they have left your team.

Personally, I have always kept my door open to former team members, helping them navigate their careers long after we have parted ways. This isn’t charity. It’s understanding that your leadership decisions have lasting impact on real people’s lives.

You Handle Fair Compensation
I strongly dislike negotiating salaries downward. I prefer paying people more than they expect, understanding the extraordinary commitment creativity demands. Creative professionals do not simply switch off when they go home so ensuring money isn’t a worry is crucial.

When your team is stressed about rent or whether they can afford decent equipment, they’re not bringing their best creative energy to the work. Your job is to remove that barrier.

You Fight for Investment
It’s not enough to pay salaries. You must convince the business to invest significantly in your team. This means securing funding for the latest technology, continuous education, and meaningful team-building experiences.

I have observed departments abundant with resources and seen resentment build in teams whose leaders haven’t successfully made the business case for investment. Your team notices when you’re not fighting for them, and they notice when you are.

You Deliver Consistently
Leaders must deliver projects on time, within budget, and meet quality expectations. You anticipate scope, resources, and stakeholder expectations long before the project kicks off. It’s educated guesswork backed by experience, planning, and intuition.

This is where the real work happens. Not in the creative execution, but in the orchestration of everything that makes great creative work possible.

You Own the Failures
When things go wrong, the responsibility falls squarely on your shoulders, even at the cost of your own reputation. Conversely, when your team succeeds, you highlight their achievements, ensuring they receive the deserved recognition.

This is perhaps the hardest part of leadership. Taking the heat when projects fail while stepping back when they succeed. It goes against every instinct, but it’s what separates real leaders from people who just like having authority.

The Reality Check
Leadership, in reality, is not glamorous. It is weighty, often invisible, and always demanding. If you deeply love the craft, stay close to it for as long as possible. Transition into leadership not because of status or the desire to delegate, but because you are ready and somewhat comfortable with the immense responsibility it entails.

Remember, leadership is caring for your team’s growth, not just handing out tasks. The moment you start thinking of it as just delegation is the moment you’ve missed the point entirely.

Keeping Remote Teams Connected

Simple rituals that kept our global design team aligned, motivated, and human. No matter where we worked from.

After the world shifted to remote work, MOHARA decided not to snap back.

Even after offices reopened, remote remained optional. We had hubs in the UK, South Africa, and Thailand, but no one was forced to show up. I was based in Bangkok. My design team was spread across South Africa, Portugal, Spain, and the UK. Sometimes working from home, sometimes working from somewhere new. It worked because we made it work.

Compared to engineering, design was a smaller team. And unlike engineering, design often felt isolated, especially in early-stage product work where generalist designers are embedded solo in startup teams. That’s why we built team rituals. Not performative. Not corporate theatre. Just consistent human habits to keep people aligned, supported, and inspired.

Here’s what worked:

Daily Standups
Every day, we’d jump on a quick call. Not just to list tasks, but to hear each other. Talk through roadblocks, share updates, vent, laugh, refocus. I’d use this moment to zoom out and re-align the team. It made each day feel connected, even when people were working alone on different projects.

1:1s That Actually Mattered
We made space for weekly check-ins. But many of the team dropped in more often to show work, talk career goals, get feedback, or just chat. It wasn’t pressure. It was presence. It was about making sure no one felt like they were figuring things out alone.

Design Training
From interns to seniors, we ran regular sessions. Foundational theory, tools, critiques, frameworks. There’s always something to sharpen. It helped us maintain high standards and grow together, regardless of timezone or title.

Monthly Design Retros
Outside of project retros with engineers and PMs, we had our own space as designers. A place to reflect on what wasn’t working, propose improvements, and bring ideas to the table. It gave us agency. We fixed things as a team, not just as individuals.

Design Quiz
Yes, a quiz. On theory, history, trends. Things designers should know beyond Figma. It wasn’t about scores or hierarchy. Just friendly competition, smart questions, and learning outside the typical project grind.

Design Onboarding
Every new designer got a proper introduction to how we worked. Our roles, tools, rituals, principles. Not just access to files, but actual orientation. It gave everyone confidence and context from day one.

Getting to Know You
One of our designers suggested adding a few random personal questions to our team calls. Where you grew up, what your guilty pleasure was, your weirdest food experience. It became a team favourite. We discovered things we never would’ve otherwise.

Playlists
We launched the MOHARA Mixtape. Weekly Spotify playlists submitted by the team. Different cultures, different sounds, one shared experience every Friday. It was a simple way to celebrate our global roots.

Food Challenges
It started with a debate over the best sandwich. It escalated into full-blown themed food competitions. We’d record ourselves cooking and eating, then vote on winners. Sandwiches, burgers, desserts. I proudly took the burger crown.

Remote Working Rhythms
Time zones were a reality. People worked from home, from airports, from beaches. We didn’t expect everyone to be online at the same time. We just agreed on a window of overlap. A shared four-hour block where everyone would be available for meetings, feedback, and connection. For some it was the start of the day, for others the end. It gave us enough structure to stay in sync without forcing anyone into rigid schedules.

These rituals weren’t complex. They weren’t expensive. But they worked.

They kept us connected not just as colleagues, but as people.

There were plenty of company-wide initiatives too, but these were the ones that made our designers feel like a team, even from opposite sides of the world.

What are the small things you’ve done to keep your team together?

Be a Kind Creative

It costs nothing, but means everything.

The creative industry is in a weird place.

We’re adapting daily, trying to stay relevant while everything around us feels like it’s shifting. Budgets are tighter. Expectations are higher. AI is encroaching. Clients want more for less. Designers are burnt out. Recruiters ghost. Teams are under pressure. Senior talent is being pushed out, junior talent is underpaid and overworked, and those in the middle are stuck holding everything together.

It’s hard out there.

But here’s the thing. We don’t have to make it harder for each other.

Too many people in this industry treat each other like competition. They act like someone else’s win automatically means their loss. Some even tear others down just to feel taller. That behaviour doesn’t reflect the talent or heart this industry is built on.

There’s no need to feel threatened by someone else’s talent, or their post, or their success. We’re all just trying to get paid doing what we love. That’s it. No one is out to take anything from you. Most people are simply looking for a little recognition, a sense of community, and a reason to keep showing up.

So here’s a thought. Just be a little nicer.

If you see something good, give it a thumbs up.

If someone looks happy, leave a heart.

If it made you laugh, use the damn laughing emoji.

If someone said something smart, thank them.

Seriously. That’s it. It’s not performative. It’s just human.

You never know what someone is going through. That one bit of kindness might be the thing that keeps them going. A small gesture can carry more weight than anyone realises.

Share your thoughts. Add something helpful. Offer your perspective. Give credit when it’s due. It doesn’t take much. You don’t need to post motivational quotes or start every comment with “Love this!” Just show a little appreciation. You might be the only person who does, and that might matter more than you’ll ever know.

We’ve all heard Jony Ive speak about caring deeply for the work. What about caring for the people doing the work. That part matters just as much. Maybe more. Because good ideas don’t come from stressed, bitter, isolated people. They come from people who feel seen, supported, and respected.

This might read like one of those toxic-positivity Instagram posts that usually get an eye roll. But this isn’t that. This is just from the heart. I’m tired of watching talented people turn cold on each other. Especially when they’re far more alike than they think.

The saddest part is seeing two creatives with the same experience, the same passion, and the same energy treat each other like enemies. That kind of behaviour comes from ego, insecurity, or some strange need to feel superior. It’s unnecessary and unkind.

At the very least, we can all be professional.

Tearing down someone’s work serves no purpose.

If there’s real feedback, offer it constructively.

If there’s nothing helpful to add, silence is better than cruelty.

Hate speech isn’t critique. It’s not useful. It helps no one. Not even the person who posts it.

This industry is already tough. What we all need is a little encouragement. A little kindness. A smile, even if it’s just in the form of a blue thumbs up.

Be a kind creative.

It’s free.

And it might just save someone’s day.

A Cautionary Tale for Designers Who Want to Lead

Many designers are chasing the next promotion before they’ve done the work that earns it.

There’s a growing trend to focus on levelling up instead of levelling in. Asking for bigger titles, more money, and more influence before proving your value. Ambition isn’t the problem. But skipping the hard parts is.

You can’t bypass the reps. And you can’t shortcut leadership.

Promotions Don’t Make Leaders
Being promoted doesn’t mean you’re a leader. It means someone has given you a new title.

Leadership isn’t about hierarchy or job titles. It’s about behaviour. About taking ownership, earning trust, and helping others grow. That often starts long before you’re officially in charge.

Many designers believe that climbing the ladder will unlock status, respect, and financial freedom. The title becomes the trophy. But leadership is not a reward for tenure. It’s a responsibility. One that gets harder, not easier, the higher you go.

The Job Changes. So Must You.
Being a manager doesn’t mean doing more of what you’ve always done. It means doing less of it and helping others do it better.

You move from creator to multiplier. From crafting the work to coaching the team. From being measured by what you make to being measured by what others make under your guidance.

You’ll need to give up control. Step away from the pixels. Start making decisions that impact people’s careers, not just the creative output. Most of those decisions aren’t glamorous. They’re messy. They involve budgets, resourcing, performance issues, and emotional intelligence. That’s the job.

Less Praise, More Pressure
One of the hardest lessons for new leaders is how little recognition you get.

You will not be thanked as often as you expect. You may be resented for having authority. You’ll be the target of frustration, even when you’re doing the right thing. Your decisions will be questioned. Your intentions misunderstood.

You are unlikely to be liked by everyone. If you’re lucky, you’ll be respected.

This isn’t a popularity contest. You’re here to create clarity, uphold standards, and carry the weight of responsibility. It can be lonely. But that’s part of the role.

Leadership Is Earned in the Reps
There is no fast track. The work always comes first. You have to build the foundation before asking for the corner office.

Learn how to think beyond the screen. Understand the business. Learn to manage time, energy, and expectations. Make peace with the fact that you’ll rarely be the one doing the work anymore. Your impact will come from elevating others.

Real leadership starts when people begin to follow your example without being told. When they look to you for direction, support, and inspiration. When your presence helps them become better at what they do.

Do Great Work, Then Share the Credit
Leadership requires humility. It requires you to give away the spotlight and take full responsibility when things go wrong. To protect your team and back their decisions. To lead by example, not ego.

This is not to discourage you. Leadership is vital. Good leaders shape the culture, raise the bar, and leave lasting impact. But it is not something you ask for. It is something others ask of you.

So enjoy where you are. Make things you’re proud of. Learn from the leaders who inspire you. Build your character before you build your title.

Then one day, when someone asks if you’re ready to lead, you’ll be able to answer with confidence.

And if you’re already making that transition and want support navigating it, I coach senior designers stepping into leadership. Get in touch if that’s a conversation you want to have.

The Best Creative Leaders Are Experienced

The best creative leaders are not just charismatic, visionary, or full of bold ideas. They are not great simply because they can sell a concept, win a room, or energise a team. What sets them apart is something quieter and more difficult to define. It is the depth that comes from lived experience. The kind that builds resilience, sharpens judgment, and shapes taste over time.

When skill isn’t enough

Becoming a Creative Director at 30 came with confidence and capability. There was strong expertise in digital, and creative direction came naturally. Projects were delivered. Clients were impressed. Teams moved fast. But beneath the surface, something was missing.

That gap only became clear when working alongside more seasoned creative leaders. They moved differently. Their feedback landed with clarity. Their presence created calm in moments of chaos. There was no need to posture or push. They had earned their authority through repetition, reflection, and results.

In contrast, early leadership was still tied to control. There was ego in the room. Pressure to prove value. A desire to push work through rather than pull the best out of people. The title had arrived before the maturity to carry it well.

Taste is not a trend

One of the clearest markers of experience is taste. Not style. Not trend-awareness. Taste.

It does not come from scrolling through curated portfolios or collecting references. It is shaped slowly over time through exposure, curiosity, and failure. Travel, music, writing, architecture, silence. The best creative leaders absorb the world. That depth filters into how they see, what they question, and how they guide others toward quality.

The most seasoned creatives can spot what others miss. They are not distracted by noise. They focus on what matters. Their instincts have been tested enough times that they can lead without overexplaining. This kind of taste cannot be taught in a workshop. It is cultivated through attention and intent.

What experience really gives us

Time in the product world made this even clearer. In fast-moving teams and high-growth environments, it is often execution that gets rewarded. But in the long run, the creatives who consistently raise the bar are not just fast or clever. They have depth.

Experienced leaders carry perspective. They have lived through changing technologies, shifts in team dynamics, and cycles of burnout and renewal. They know when to push and when to protect. They understand how to create space for others to grow, not just deliver. And they bring calm. Not because things are easy, but because they have faced harder before.

This is not about age. It is about exposure, repetition, and reflection. It is about the ability to hold both the work and the people with equal care.

Creative leadership is legacy work

A creative leader is not measured only by the work that gets produced under their watch. They are measured by the people they develop. The teams they shape. The future leaders they inspire and send forward.

The best creative leaders do more than oversee projects. They mentor, coach, and protect. They raise standards without crushing spirit. They teach others how to see more clearly, make better decisions, and build their own confidence.

Leadership is not what you do in the moment. It is what you leave behind. The impact of a strong creative leader is often only fully understood years later, when the people they supported go on to lead others with the same principles. That is the true legacy.

For those stepping into leadership

Ambition is a powerful driver, but titles arrive faster than depth. New leaders benefit most from being close to those who have done it well for a long time. Not just for inspiration, but for calibration.

It is not just about learning how to give feedback or present ideas. It is about learning when to hold back. When to pause. When to invest in someone quietly, with no immediate return. These lessons are rarely written down. They are observed, absorbed, and eventually practised.

For those hiring creative leaders

Experience should not be a risk factor. It should be a requirement.

The tendency to chase novelty over wisdom is short-sighted. The most experienced leaders bring more than just ability. They bring consistency, clarity, and confidence. They know how to balance quality and pace, ambition and sustainability. They know how to scale teams without losing the integrity of the work.

Most importantly, they build people. That is what keeps standards high long after the leader has left the room.

For those with experience

There is increasing pressure to reinvent or reposition. To prove relevance. But what seasoned creatives carry is more valuable than ever.

The ability to remain calm under pressure. To make decisions rooted in principle, not panic. To spot the crack before it becomes a fault line. To listen deeply. To mentor generously. These are the traits that hold teams together.

There is no need to shrink. There is no need to apologise for the depth that has been earned. The industry needs it.

This is what moves the work forward

Creative leadership is not a performance. It is a practice.

It is built over time, through mistakes, reflection, and a commitment to growth. The best creative leaders are not defined by their output alone. They are remembered for the standards they set, the people they empowered, and the culture they helped build.

Experience is not the past. It is the foundation. And the best leaders carry it forward not for themselves, but for everyone around them.

Why I Wear Black T-Shirts

And Probably Always Will

For as long as I can remember, I’ve gravitated toward black t-shirts. What started as a simple preference evolved into a habit. Over time, it became a kind of personal uniform. Today, black t-shirts aren’t just part of my wardrobe. They’re a reflection of how I live, think, and move through the world.

A Personal Story
I started wearing darker t-shirts over two decades ago. I run hot. With a fast metabolism and an active lifestyle, sweating was inevitable. White t-shirts quickly betrayed every mark.

What began as a straightforward fix became something more. I remember finding a particular Polo branded black v-neck that fit perfectly. I bought several of the same one. Not out of obsession, but because it worked. Over time, I grew self-conscious about appearing repetitive. So I started mixing brands and subtle logo variations to keep things interesting without losing the formula.

Eventually, even that felt unnecessary. Prints faded from fashion. Clean, unbranded staples took their place. That’s when I found my ideal t-shirt. A $9 crew neck from Uniqlo. Minimal. Durable. Cut just right. I could buy it anywhere in the world. I phased out the branded versions and bulk-bought the one that simply did the job.

Now, getting dressed requires no second thought. I throw one on and look, and feel, sharp. Without the noise.

Covered in tattoos, I already stand out without trying. The black t-shirt acts as a counterbalance. I’m not a goth. I’m not trying to be mysterious. I’m just comfortable being myself.

I’ve worn these t-shirts on stage, in my videos, at the gym, and in boardrooms packed with executives. Always the same. Plain black. Flawless fit. No logos. Easily replaced. Consistently sharp.

The Industry’s ‘Uniform’
It turns out, I’m not alone. Black t-shirts have quietly become the unofficial uniform across creative industries. Design, tech, media, advertising. In places where expression matters but decision fatigue is real, black becomes a kind of silent badge of belonging.

In the film industry, it’s almost a joke. You can always spot production crew by the sea of black. It is tactical. Black doesn’t catch stage lights. It hides stains. It lets the work, not the wardrobe, take centre stage.

Across creative and production circles, the black t-shirt is more than a trend. It is a tool. Whether you are a designer, a director, a developer, or a producer, a black tee says: I’m here to build, not perform. It is neutral. It is functional. It is part of the unspoken language of people who solve problems behind the scenes.

Steve Jobs and Mark Zuckerberg understood this intuitively. Jobs’ black turtleneck. Zuckerberg’s grey t-shirt. It wasn’t about fashion. It was about protecting focus. Minimising the trivial. Maximising the important.

Others have embraced the same idea. André 3000, once known for bold style, now lives in uniformed dungarees. A reflection of his evolution. Matt D’Avella, the filmmaker behind Minimalism, adopted a personal uniform and even extends it to his newborn. Same outfits. Fewer decisions. More focus on what matters.

Interestingly, while Zuckerberg once championed simplicity, he has lately pivoted toward a more colourful wardrobe. Some see reinvention. To me, it reads closer to midlife restlessness than useful evolution.

Even in science fiction, uniform dressing isn’t accidental. Think of Star Trek’s iconic uniforms. Clarity. Identity. Order. In real life and fiction alike, uniformity reduces distraction and sharpens collective focus.

Why It Works For Me
I know myself. I’m a creature of habit by design, not by default. I value efficiency. I believe that starting the day without wasting energy on trivial choices is a quiet form of discipline.

It is a tactic against decision fatigue. The mental drain that comes from making endless small decisions. James Clear, in Atomic Habits, talks about reducing friction to improve incrementally every day. Wearing black is my personal version of that. One less decision. One more edge.

Minimal. Clean. Casual. Functional. Sharp. That’s my style. I don’t need loud brands or showy logos to feel confident. Being in shape, I don’t crave extra attention through clothing. I often see loud fashion as less about personal taste and more about flexing supposed wealth.

True wealth, the kind that doesn’t shout, has always done it differently. Those with old money don’t plaster themselves in other people’s brands. They wear well-constructed, beautifully tailored, quietly confident pieces that speak for themselves.

That’s the ethos I believe in. Confidence should radiate naturally, not through stitched-on labels.

I blend in when I want to. I stand out, paradoxically, by not trying to. A black t-shirt lets me move through different worlds. Boardrooms. Studios. Gyms. Without losing myself.

Reining It In (Or Not)
The rest of my wardrobe evolved the same way. Traveling through Southeast Asia sharpened my eye. Clothes needed to be versatile, lightweight, and enduring. Black became the natural answer.

I also realised how much clothing we accumulate and barely use. It is wasteful, financially and environmentally. That insight changed how I buy.

Today, I invest only in pieces that are built like tools. Engineered. Technical. Purposeful. Outdoor gear like Terrex by Adidas. Durable, functional warmth like The North Face. Pieces where every stitch has a reason and earns its keep.

My wardrobe today is deliberate, not accidental. Everything works together. Everything is used. Everything has a reason to be there.

That said, I do feel the occasional pull toward more colour. I used to mix it into sneakers, trousers (never denim), and hoodies. There is still room for evolution.

But when the dust settles, simplicity always calls me back.

The Bigger Picture
This was never really about clothes. It has always been about making life simpler, removing unnecessary choices, and focusing on the things that actually matter.

Wearing black makes my days easier. It saves energy for the work I care about. It keeps me consistent without feeling restricted.

It fits who I am, how I live, and how I work. And after all this time, I still wouldn’t change it.

CEO’s Your Design Team is Broken

What CEOs need to know about the state of their design function
If your design team isn’t delivering what you expect, the issue may not lie with them. It may be everything around them.

Most CEOs do not have direct visibility into the design function. It often sits under digital, technology, or marketing, far removed from the boardroom. The information reaching you is filtered through layers of leadership, metrics, and assumptions. What looks like slow progress or underwhelming output is usually the result of poor structure, misplaced priorities, and a culture that makes great design difficult to deliver.

You might be feeling the pressure to modernise, especially with the rise of AI promising faster results and leaner teams. But in the rush to stay competitive, there is a growing risk of sidelining your design team just when you should be investing in them most.

This is not about blame. It is about awareness.

Here is what you need to understand in order to unlock the real value of the team you have already invested in.

Broken Hiring and Team Structure
Most design teams report into departments that are not design-led. They sit under technology, digital, or marketing functions, none of which are structured to prioritise or nurture design thinking. This removes design from the strategic level and positions it as a service or support layer. As a result, critical product and experience decisions are often made without meaningful design involvement.

In some cases, the person leading design has no background in the discipline. They may have transitioned from project management or operations, completed a short course at a fancy university that gave them superficial credibility, and stepped into a leadership role because they aligned with the right internal stakeholder. They may be great at reporting upwards, but they often lack the experience to guide design teams through complex, ambiguous challenges.

The consequences of this are long-term. You end up with bloated teams made up of junior staff with no mentorship, senior staff with no authority, and design leaders who cannot lead. This is not a problem of resourcing. It is a problem of structure and responsibility.

Toxic Work Culture
Design thrives in environments that support focus, autonomy, and exploration. But most corporate workspaces are designed for consistency, control, and operational efficiency. Designers are often asked to operate under the same norms as legal, finance, or HR, even though their work requires entirely different conditions.

Telling people to return to the office without addressing what they are returning to does not rebuild culture. What is the point of going into the office to have a Zoom call?

Open-plan floorplans, generic spaces, and restricted software access do not support deep, creative work. Designers find themselves stuck in back-to-back Microsoft Teams meetings, working in environments that are not designed for thinking or problem-solving.

In many organisations, designers are not even allowed to use modern tools that would enable their work. AI tools, cloud platforms, and open-source systems are often blocked by IT, which operates from outdated security models. The result is frustration, inefficiency, and disengagement.

If the team has no space to call their own, they spend half the day trying to find a seat in the new office that has consolidated the entire company into a single space. You no longer needed those extra offices, but now you’ve decided you want everyone back.

Even small blockers, like software restrictions or micromanagement of process, can significantly reduce creative output. Trust your team more than your blanket policies.

Contractor Culture
Contractors are often brought in to boost delivery speed or fill short-term gaps. On paper, it looks like efficiency. In reality, it often leads to inconsistency and friction. These roles are usually filled through expensive consultancies that supply mid-level talent at high rates. While the external staff do their hours and move on, the internal team is left to integrate, fix, and maintain the work.

This creates a two-tier system. Contractors are protected by their agency structure, often better paid, and excluded from internal pressures. The full-time team carries the long-term responsibility, often working overtime out of fear that underperformance will lead to cuts.

Using external contractors is not the issue. The issue is how they are used. If your internal team is constantly cleaning up or onboarding new faces, you are not building capability. You are burning out the very people who are committed to your organisation.

Consultancy Dependency and Outsourcing
External agencies are often given the most exciting work. The rebrands. The campaigns. The vision decks. Internal teams are left with execution and support. This imbalance signals that the in-house team cannot be trusted with strategic work, even if they have the skills and context to do it better.

Worse still, many consultancies do not deeply understand your product, users, or constraints. They hand over incomplete strategies, over-designed concepts, or pitch-driven deliverables that cannot be executed in the real world. The internal team then spends weeks trying to make sense of it all, often with less time, less clarity, and fewer resources.

I once worked with a company that launched a major initiative built by an external agency. The work looked stunning, but when it hit the internal team, nothing fit. It did not align with the tech stack. It ignored user constraints. And it lacked any roadmap for support. Within weeks, it was stripped down and patched just to function. Six months later, the initiative was shut down quietly. The executive who championed it had already moved on. The cost was hundreds of thousands in sunk time, vendor fees, and brand credibility. All of it could have been avoided if the internal team had been trusted from the start.

This cycle creates waste. It damages morale. And it keeps design in a reactive posture.

Shiny Object Syndrome
Many businesses fall into a pattern of investing in new tools, platforms, or features without clear evidence of user need. These initiatives are often driven by senior stakeholders, rushed through third parties, and launched without integration into the broader product strategy.

At its most basic, your product needs to work. That means refining the core flows, fixing small frustrations, and continuing to iterate on what matters most to users. But these basics are often neglected in favour of the new and exciting. You end up chasing parity with competitors, rushing out features to impress the board, or building tools that go unused, all while fundamental user journeys remain broken.

One of the most common mistakes is building features just because a department with the biggest budget asked for them. If you are not using data to trim the fat, identifying what is actually being used and what is just noise, then you are not managing a product. You are feeding a backlog of politics.

Most features are underused. The cost of not focusing is hidden, until the user leaves, the team burns out, or the system starts to collapse under its own weight.

Undervaluing Design
Design is often expected to drive business impact but treated as a cost centre. Salaries are uncompetitive. Career paths are unclear. Titles are capped below what the market recognises. At the same time, consultants and contractors are brought in at higher rates, given more strategic work, and publicly recognised for their contributions.

Worse still, designers are placed on internal career paths that are disconnected from how the design industry actually works. HR frameworks are often modelled after marketing, project management, or IT roles, which makes progress feel performative, not meaningful. Designers are told they cannot have the title that reflects their level because it does not exist in the internal structure. That forces them to leave to grow.

HR teams must stop treating design like an edge case and start collaborating with design leadership to define what growth looks like in this function. That means aligning your job levels, salary bands, and promotion criteria with how the industry operates.

The result is stronger retention, clearer role definition, and a team that can grow with your business instead of out of it.  AI Hype and Creative Fear

AI is changing what’s possible. With a few prompts, you can now create visuals, motion, and layouts that once required the most experienced specialists in the industry. That’s real. But design is not just execution. It’s not something you automate because a dashboard looks good or a pitch deck said so.

When leadership buys into the hype that AI will replace creatives, your team hears it loud and clear. Not as a challenge. As a threat. Instead of being empowered to explore what these tools could unlock, they brace for impact while consultants fly in to present generic strategies designed to sell more software, not solve your specific problems.

AI will not design for you. It will not understand your business. It will not ask the right questions, navigate trade-offs, or tailor solutions to your users. The companies that win are the ones that give their team time to think, space to test, and permission to build better. The ones that lose will chase the trend, generate faster versions of the same broken experiences, and call it innovation.

Disconnected Teams and No Source of Truth
You already have a design system. If you have a product in market, you are relying on shared patterns, components, and conventions. But what was once a tool for clarity and alignment becomes useless when it’s handed off to people who don’t understand its purpose, treat it as a side project, or let it grow without guidance.

Eventually, no one trusts it. Design teams create their own versions. Engineers build around it. Contractors ignore it entirely. Visual inconsistencies creep in, decisions aren’t recorded, documentation is outdated, and every new project starts with a mess someone else created.

This isn’t just inefficient. It erodes brand trust, slows teams down, and disconnects your product from the people building it. You can’t keep scaling teams without a shared foundation. You can’t deliver quality when no one knows what good looks like. And you can’t claim to be design-led if your design system is an abandoned folder full of guesswork.

So How Do You Fix It?
If your design team is underperforming, it is not about adding more people. It is about improving the conditions they work in. Here are eight actions you can take to shift from underperformance to long-term value.

Fix the org chart
Design should not report into functions that see it as decoration or support. It should be led by an executive who has actually built design teams and products. This gives design a voice in key decisions and ensures that user experience is considered early, not retrofitted later.

You need to hire a design leader who does more than play politics well. Hire someone who is actually a designer. Someone who came up through the design industry. Someone the team will respect because they are one of them. Someone who has been on the tools, shipped real work, and knows the pressure of delivery. They will not be doing the hands-on work anymore, but the experience they bring becomes something the team can aspire to, be motivated by, and learn from. Real credibility, not just corporate credentials.

In fact, some functions could benefit from reporting into design. Marketing’s primary job is to market the product. If they are communicating a brand message that the product cannot deliver on, that is not just a problem for design. That is a trust problem for your business. Marketing output should align with the experience, and design should have sign-off to ensure that happens.

The impact is a more cohesive experience, fewer internal clashes, and stronger alignment between what the business promises and what the user actually gets.

Build a real team
Contractors are not your core team. They are there to roll out delivery work so your main players can move to the next challenge to solve, like a Seal Team 6. Your best designers should be free to tackle the high-value problems, not trapped in day-to-day production cycles.

While it makes sense to structure around squads, you also need specialists who can move quickly, snipe the biggest problems, and keep momentum alive. Back this up with a strong design ops function whose job is to onboard contractors quickly, plug them into the toolchain, and keep the internal team focused on what matters most.

This leads to lower attrition, reduced dependency on external support, and a team that is solving real problems, not just getting work done.

Respect the environment design needs to thrive in
Designers need desks. They need walls. They need messy spaces covered in inspiration and personal touches that feel like their own. Give them a place to belong, not a hot desk next to someone measuring quarterly compliance reports.

Let them shoot the shit, sketch ideas on the furniture, be noisy when they need to, and express themselves freely away from the school hall monitors who kill creative flow. And do not let the corporate machine fill another room with the same grey furniture bought in bulk. Invest in their space the same way you invest in your brokers’ bullpens and their sixteen-monitor setups.

You will see higher-quality thinking, stronger team cohesion, and an environment where creativity is not squeezed out of existence.

Stop outsourcing the fun stuff
Bring in consultancies when your team asks for them, not when leadership feels insecure. Use them to support your team, not to undermine them. Hire specialists who add new thinking or depth, not another rinse-and-repeat pitch deck written by people who will never stay to build anything.

Your in-house team knows your systems, your constraints, and your users. Trust them to lead, and when they call for backup, back them up. Do not replace them.

This produces more consistent design, lower costs over time, and a team that is invested in the outcome, not just the process.

Kill the shiny-thing pipeline
Use your own people to tell you where to focus. Ask your design team to show you what is happening in market, what they are seeing, what users are gravitating towards. Let them bring ideas to the table before you hire a research company or listen to a suit pitching the next shiny thing.

Refocus on data, craft, quality, and focus. Build what aligns to your product and your brand, not what looks good on a roadmap presentation. Be true to what you are. Stop trying to be everything to everyone and producing watered-down experiences that offer no real value and even less return.

Done well, this leads to better adoption, reduced delivery waste, and stronger, more differentiated products.

Pay them like they matter
Design is not an optional extra. It is how customers experience everything you offer. You cannot say design matters while locking designers into capped salaries, internal-only career frameworks, and fake progression paths designed to tick HR boxes.

Pay competitively. Recognise design-specific seniority. Let your best people grow inside the business instead of forcing them to leave to earn what they are worth. If they have to choose between loyalty and survival, survival wins.

That is how you build loyalty, retain institutional knowledge, and compete for top-tier talent that powers real growth.

Empower your team to lead your AI adoption
Form a dedicated research and development squad inside your design team whose sole focus is testing, validating, and integrating AI tools that actually fit your work. Let them experiment, run pilots, and work directly with other designers to stress test what fits the toolchain and adds real value.

Educate the entire design function on how to effectively use these tools. Make AI a lever that enhances creativity, reduces grunt work, and unlocks new thinking. Not something imposed from the outside by vendors with a quarterly target to hit.

You will gain faster workflows, smarter solutions, and a team that becomes stronger and sharper, not weaker and cheaper.

Invest in your design system and treat it like infrastructure
Make using the design system mandatory. Not to limit creativity, but to give it a strong foundation to build on. Your system is not a set of rules. It is a platform for faster delivery, better consistency, and higher quality without reinventing the wheel every time.

Empower teams to innovate inside the system. Free them to spend more time solving real problems instead of cleaning up inconsistency. Constantly educate, communicate, and demonstrate the value it brings. Build unity, not division.

Staff the system with your best designers, the ones who obsess over every pixel, token, and principle. When you build a system that others want to contribute to, you create a centre of gravity for everything your design team builds.

When treated seriously, it becomes the single most efficient way to scale quality across your entire business.

Final word
If you’re serious about building better products, delivering better experiences, and creating long-term value, then your design team needs more than praise. They need power. They need space. They need leadership that understands their value and an organisation structured to support it.

And no, letting them wear black t-shirts and trendy sneakers while you throw around buzzwords like “customer experience” does not count. That is not investment. That is theatre.

You cannot keep treating design like a downstream service and expecting upstream impact. You cannot outsource vision, underpay talent, overrule process, and then wonder why things do not work. And you definitely cannot keep waiting for someone else in the business to fix it, because no one else will.

If you have built an in-house design team, you already have what you need.

But until you create the conditions for them to thrive, you will never get the return you are hoping for.

This is not about giving design more. It is about expecting more, by making the right investments, setting the right structure, and finally giving it the seat at the table it deserves.

The companies getting design right are already outpacing you. It is not too late to catch up. But it is on you to lead the change.