Craig – Craig Jamieson

Digital Shaped a New Kind of Creative Director

You might expect creative directors to be digitally native these days, but this was not always the case. When I entered the advertising industry agencies hired people like me for our digital experience. Traditional creative leaders barely understood what digital was, never mind how to deliver it. Let me take you through that journey so you can see why this background produces creative leaders who are operating on an entirely different level.

I spent more than a decade working independently before I joined Ogilvy. I started designing in 1998, taught myself everything and delivered full projects end to end. Back then the only work you could consistently find online was traditional advertising, so I learned the industry by studying the best print, TV and brand campaigns from around the world. That exposure shaped my sense of craft and helped me understand how traditional creative thinking worked long before I ever entered an agency.

In 2007 I was approached to be a Creative Director at a digital agency, but after six months I left and continued on my own. When the recession hit in 2008 I had to explore new options, and in 2009 I entered the advertising world full time.

My move into advertising was not a natural transition. Traditional agencies were built around writers and art directors, and digital was treated as an add on rather than a core part of the work. The digital landscape itself was still taking shape. We were building microsites, putting local brands online for the first time, creating rich media banner ads, experimenting with early social media, exploring mobile formats and figuring out how to bring technology into campaign ideas in ways people had never seen before. I stepped into environments where digital was expected, but very few people understood the channels, the platforms or the production required to make any of it work.

That gap in understanding meant I ended up carrying far more responsibility than the title suggested. I was expected to lead digital, but I was also expected to support traditional teams, help shape campaigns, guide the craft, ensure the ideas could live across channels and solve the technical challenges that came with them. I was directing visuals one moment, shaping interaction flows the next, reviewing code, fixing production problems, helping pitch ideas and building the assets needed to bring everything to life.

At the same time digital teams were rarely given the support that matched the expectations placed on us. Traditional teams had established roles, departments and processes behind them, while digital was expected to deliver at the same level with a fraction of the time, budget and resources. We often had no writers dedicated to digital, no art directors who understood the medium, no motion or animation support and limited development capacity. Budgets were smaller, timelines were tighter and the pressure was higher, yet the work still had to feel seamless within integrated campaigns.

It also meant I stepped into leadership with a very specific challenge. I was highly skilled in the work because I had done everything myself for years, but that did not mean I had a team who could deliver at the same level from the start. I had to learn how to articulate direction clearly, guide people through execution and trust them to carry ideas forward, even when I knew I could produce the work faster and to a higher standard. Balancing that with the expectations of clients, the demands of production and the speed of agency life became one of the most intense parts of the role.

As digital expectations grew the traditional side of the agency relied on me more than anyone realised. I was pulled into campaign development, pitch strategy, brand work and anything that required a deeper understanding of how ideas translated into real experiences. While traditional creative directors had writers, art directors and production teams supporting them, I often had to cover multiple disciplines myself while helping lift the broader creative department at the same time.

A lot of the work that won integrated awards in those years only qualified because the digital teams made it real. We built the microsites, the experiences, the mobile components, the social integrations, the data capture and the interactive mechanics that allowed traditional ideas to be entered into bigger categories. In many cases we even hosted elements on our own servers just to ensure the work existed online. Yet our names were rarely included in the credits, even when the work could not have been entered without what we built. And when it came to entering our own digital work we almost never had the budget, because our departments were consistently underfunded despite carrying the heaviest load.

On top of all that there was almost no operational support. Traditional teams had traffic managers, producers and well defined structures behind them. Digital teams often had none of that. We were writing briefs, estimating work, scoping development, managing production, handling QA, preparing files, coordinating with media teams and chasing down missing assets while still delivering the creative. It was leadership, production and execution all happening at once, every day, with no buffer and no safety net.

The further I moved into senior roles the more this complexity increased. I was running digital, supporting traditional campaigns, leading pitches, shaping technical solutions, guiding creative teams, educating clients and filling the gaps between departments because digital touched everything. Traditional structures were not built for this level of integration, so I had to create my own ways of working, define new processes and build bridges between teams so the work could move faster and with more consistency.

As the role expanded I was also expected to take on the leadership responsibilities that come with senior creative positions. This included hiring, giving feedback, managing performance, handling sensitive conversations and making decisions that affected people and the business. I had run my own studio for years, but formal HR practice was completely new to me. There was no handbook and very little support. I learned how to lead teams in real time while carrying all the creative, technical and operational responsibility the work demanded. Far more than my fellow creative directors shouldered in the traditional side of the agency, this was handled by our ECD.

Despite everything the work still had to be delivered at the same standard as traditional campaigns. Clients did not care about the lack of support or the limitations we faced. They expected the work to look polished, feel seamless and function perfectly. Every digital asset had to be designed, developed, tested, refined and launched with the same level of craft associated with TV, print, radio, activation and brand work. There were no shortcuts, and the pressure to get it right was constant.

Traditional teams had dedicated DTP artists, film crews, photographers, retouchers, sound engineers and production partners behind them, while digital teams often had none of that support. We had to source imagery, create motion, design interactions, test functionality and build entire experiences with limited help. Every component had to be crafted by hand, and the responsibility for quality landed entirely on us.

On top of that we were building work for channels that changed constantly. Platforms updated, browsers broke things, devices behaved differently and nothing stayed stable for long. Every project required new problem solving, new methods and new technical decisions. Traditional campaigns could rely on fixed formats. Digital work had to adapt in real time, and the pressure to keep up never stopped.

All of this happened while still carrying the expectation to contribute to traditional creative work. I was brought into print reviews, TV concepts, radio scripts, activation ideas and brand discussions because my perspective helped strengthen the work. Even without formal training in those disciplines I could hold my own, guide direction and help sell the ideas. Years of learning from traditional work gave me an instinct for it, and that made it easier to bridge the gap between old and new ways of thinking.

That ability to move between worlds became one of the biggest advantages people like me brought into agencies. Traditional teams understood storytelling, craft and brand, but digital required a level of technical depth they were not equipped for yet. I understood both, so I became the person people turned to when ideas needed to work across every channel. It meant more responsibility, more pressure and less room for mistakes, but it also meant the work reached a higher standard because every angle was considered.

We also had to fight for equipment that could keep up with the work. We were not only surfing for inspiration, doing mockups, moodboards and pitch decks, we were designing full experiences, creating motion, exporting assets, testing builds and preparing production files that pushed machines to their limits. Slow hardware did not just make the work frustrating, it added hours to already tight timelines. Yet our budgets for tools, software and machines were minimal. Traditional teams had production partners and established pipelines. Digital had to deliver everything with underpowered equipment and shared resources, even as the expectations kept rising.

Many days were spent educating the agency as much as producing the work. I was explaining platforms, formats, constraints, possibilities and risks to people who had never worked in digital but were expected to sell it. I had to translate technical challenges into language clients could understand, guide account teams through decisions they had never managed before and teach creatives how to integrate digital thinking into their ideas. It was part leadership, part production and part ongoing education, all happening alongside the actual delivery of the work.

Client expectations added another layer of pressure. Digital was still new to many of them, so they wanted certainty in a space that changed every few weeks. We had to reassure them, manage their fears, guide their decisions and take responsibility for outcomes even when the platforms, tools or technologies were unpredictable. Traditional campaigns had decades of precedent. Digital had none. Everything we delivered carried risk, and every problem became our problem to solve.

Inside the agency that responsibility expanded even further. I was pulled into every pitch that required a digital layer, and almost every brief came with that expectation. While traditional teams could focus on concept and craft, digital had to work out how the idea would function, scale, adapt and be built. I was shaping creative, mapping interactions, exploring technology, scoping effort and helping sell the solution, often all in the same meeting. Pitch work was relentless, and digital was expected to make every idea bigger, smarter and more integrated without ever slowing the team down.

All of this happened while still running a team that needed guidance, feedback, mentoring and direction. People relied on me to help them grow, to set standards, to solve problems and to make calls when things got tough. I had to balance their development with the workload, protect them from unrealistic demands, keep the quality high and push the work forward even when the pressure was heavy. Leading a digital team meant carrying responsibility for both the people and the output at a level few truly understood.

Despite the pressure I loved the work. Digital gave me freedom to imagine things that did not exist yet and build experiences people could interact with. It let me combine design, technology, storytelling and craft in ways no other channel could. The work demanded constant learning and constant reinvention, and that challenge kept me sharp. Even in the toughest moments there was satisfaction in solving the problems, delivering the impossible and proving how powerful digital thinking could be when it was done well.

That background became even more valuable when I moved into in house product work. Instead of fast campaign cycles I was working with engineers, product managers, analysts and business teams to build systems, tools and platforms that needed long term thinking. The same instincts that helped me shape digital ideas in agencies helped me define user journeys, refine interfaces, guide content and influence brand and marketing work. I could bridge conversations between design, engineering and leadership because I understood how everything connected.

Even inside a product environment the expectations did not shrink. I was still contributing to brand, shaping creative direction for marketing, advising on campaigns and helping teams find clarity in the work. The difference was that everything had to scale. Every decision affected thousands of users instead of a single campaign cycle. The responsibility grew, but the years of navigating complexity in agencies made it easier to handle.

That is why digital creative directors bring something different to the table. We did not only learn how to give direction, we learned how every part of the work is made and how to guide it from idea to delivery under pressure most people will never see. We had to adapt to new platforms, new tools, new behaviours and constant change, long before the industry understood the value of that skill set. So when the world shifted again into product, systems, experience and now AI, it was a natural progression. The challenges we faced built creative leaders who can move across disciplines, solve problems at scale and stay ahead of whatever comes next.

Creative Direction vs Creative Director

Creative direction is a skill

Being a Creative Director is a responsibility

Over the years I have worked with people who were excellent at giving creative direction. They could shape ideas, guide tone, and bring a vision to life. The skill usually grows out of art direction or copywriting. In traditional agencies it meant defining the strategic and creative vision for a project, campaign or brand.

Giving creative direction means being able to articulate what needs to be done without being a dictator. It is about setting a clear vision, giving your team enough to build from, and having the taste to pull the right levers at the right time. Talent, experience and intuition come together here, shaping something people are proud of, aligned on, and capable of executing. Years of curiosity, exposure and craft eventually turn into creative instinct.

Good creative direction is storytelling. It helps people see where the idea could go and gives them confidence to explore it. At this level you might be leading one project or several, but the focus remains on the work. Management plays a smaller role while creative problem solving takes priority.

Being the Creative Director is different. The moment the title lands, the focus shifts from what is made to how it is made, and by whom. That is where the difference really shows.

Giving creative direction shapes the work.
A Creative Director shapes the environment where that work happens.

You are no longer just guiding an idea. Now the responsibility includes everything that surrounds it, from structure and people to culture and rhythm. Hiring, budgets, performance and growth become part of the job. Rituals are created to bring consistency and stability. Thinking expands beyond the creative outcome toward the creative function itself.

Many people who grow into this role struggle with the balance. The creative power is appealing, yet the admin and accountability are heavy. Endless meetings, budget discussions and constant context switching make the job less glamorous than the title suggests. Instead of being the one who gives creative direction, you become the one who holds the space for others to do it.

For me, this became even more complex working as a Digital Creative Director. Responsibility extended across visuals, copy, UX, technology and production. Managing structure, workflow and culture added another layer, especially in environments where senior leadership did not understand digital. That experience taught me that creative direction is earned through responsibility, not only through instinct. I will write more about that in a follow up article because it deserves its own space.

Creative direction shapes the work.
The Creative Director shapes the people behind it.
That balance defines real leadership.

The best leaders learn to do both.

There should be outrage

Agencies are consolidating, jobs are being cut by the tens of thousands, and the creative industry is being hollowed out in real time. The voices that should carry weight are silent. Maybe they are relieved it was not them this time. That silence is costing us.

This is not a handful of redundancies. It is entire departments wiped out, whole networks of talented people with decades of experience suddenly unable to find work. Professionals who once had their pick of opportunities are sending out applications for months and receiving nothing more than automated rejections, if they hear anything at all. People with long careers are now locked out of interviews altogether.

AI itself is not the enemy. The technology has enormous potential to accelerate creative processes, to open new forms of expression, and to remove repetitive tasks that held people back. Used responsibly, it could help teams imagine, test and deliver at a speed that was never possible before. The promise is there, but the reality is very different.

AI does not create new clients or expand the number of people with money to spend. If the majority are unemployed or underpaid, there is no market for services, no audience for products, no demand for creativity. Wealth concentrated in the hands of the ultra-rich narrows the pool of opportunity. Faster delivery and cheaper production mean nothing if there is nobody left with money to pay for it.

The issue is not only the jobs being cut but the complete absence of any new economic foundation to replace them. Governments are doing nothing. There is no accountability for companies that erase tens of thousands of jobs overnight. There is no serious debate about universal basic income. When it does appear, it is framed as an insulting figure, five hundred bucks a month, an amount nobody can live on. If people are being denied the chance to work, then a real living income is the only solution. Anything less is abandonment. Add a few zeros if leaders want to pretend they are serious about the future.

At the same time, new roles are being promoted as innovation when they are nothing of the sort. Neo humanoid robots are being rolled out, controlled remotely by humans through headsets. The cost to rent one is less than five hundred dollars a month. Whoever becomes the eyes of that machine will be earning even less. Work has been reduced to operating a robot body at poverty wages while someone else collects the profit.

The creative industry is being squeezed from every direction. Teams are replaced by bots trained on stolen IP. Agencies are reduced to brand names attached to automated systems. Freelancers are left competing for scraps, forced to slash their rates while clients dictate every term of every contract. What remains is not a healthy marketplace but the dismantling of one.

AI is powerful and nobody disputes it. But technology cannot replace the wider economic ecosystem that allows people to live, work and spend. Without that foundation, AI only accelerates the divide. The wealthy consolidate even more while the majority are pushed out entirely. What is being called democratisation is in practice exclusion.

This industry was built by people who dedicated their lives to the work. They are being treated as disposable. Governments are looking the other way, protecting billionaires while leaving tens of thousands with no jobs, no income and no safety net.

AI is being positioned as the future, but the present reality is brutal. Workers are being discarded at scale, survival is being left to chance, and the silence surrounding it is not just disappointing, it is dangerous.

Where is the outrage?

Leadership Is Earned Through Experience

The advice that circulates around senior hiring often misses the point. Trim your history so you appear less intimidating. Add more design examples, then remove them. Keep case studies short because nobody reads, although some will argue they should be long to show the process. You may be told you are too experienced and at the same time not relevant enough. Branded too expensive, even though there has never been a conversation about money. These contradictions reveal a misunderstanding of what leadership really is.

At a certain level, the role is no longer about a title. It is about the job. With depth of experience, you move beyond the career path you first aspired to. You exceed the most senior of practitioner roles, lead people who once did what you did, and step into positions that are focused purely on leadership. Eventually you become the leader of those leaders, shaping not just projects but entire functions. How can anyone argue that experience does not matter?

Design is too often reduced to pushing pixels or making things look good. That is an oversimplification. The majority of design work is problem-solving. Tools like Canva or AI can create outputs, but they cannot think. Creativity comes from framing the problem, guiding the process, and bringing an idea to life. A leader is not less creative by being less hands-on. In many cases they are more creative, because they extend thinking beyond execution and channel it into outcomes.

Think of it as a conductor. A conductor may not play every instrument in the performance, but they understand them all. They know each note in the score and bring together the orchestra to create something greater than the sum of its parts. Leadership in design works the same way. You may not be pushing pixels every day, but you know the craft, you know the detail, and you create the conditions for others to produce their best work.

This is why there is a fundamental difference between a senior designer and a design leader. A senior designer delivers excellent output. A leader builds the environment where dozens of people can deliver excellent output at scale. One is craft at the surface. The other is practice in its widest sense. Both are valuable, but they are not the same.

Yes, there are fewer opportunities at the top. That scarcity is exactly why networks and discernment matter. Placing leaders is not about uploading job descriptions. It is about knowing the industry, building trust, and understanding what it takes to succeed in complex, high-stakes roles. If you are serious about leadership hiring, you should be able to distinguish between finding a skilled designer and hiring a leader to build and run a design function. They are two entirely different things.

Bias only makes this harder. Being told you are too experienced, too old, or too expensive without genuine evaluation is as offensive as being told you are the wrong gender or race. It is unlawful, it is short-sighted, and it undervalues what experience really brings. The organisations that succeed are the ones that recognise wisdom, foresight, and proven ability as strengths. Experience builds confidence, not just for the leader but for the entire business.

If you want to build something meaningful, hire a leader who creates the conditions for great work, not just the person who contributed to one piece of it. Leadership is not theory and it is not simply a line on a CV. It is earned through years of guiding, teaching, hiring, and representing the function at the highest level.

The foundation of leadership is not education. It is not awards. It is not titles. It is experience.

The Overlooked Sidebar UI

In 2016 I introduced a design pattern into my work that I still believe is one of the most under utilised interface elements. The sidebar.

I first noticed this idea in Gmail and later in Office. Both products used a fixed panel on the right to bring in tools like calendar or tasks without disturbing the main content. It was clean, contextual and it kept people in flow. I thought it was a smart solution but when I tried to apply the same idea to other products I met resistance. That resistance still exists today.

What I built was simple. Using Angular we structured the page so that the main content lived on the left and remained responsive, while a fixed width sidebar sat on the right and could slide in and out. The layout stayed intact. The sidebar became a utility space that could support different needs without forcing people to leave the page they were on.

The first use case was chat. If you were filling in a form or browsing content and needed support you could open a conversation without losing the context of the page. This solved a real frustration. At the time chat usually appeared in a popup window, a modal covering your content or even a new browser tab. All of these broke the experience. With the sidebar the conversation lived beside your task.

Once it was working I realised the same pattern applied to many other flows. Sign in did not need to take you to a new page, you could complete it in the sidebar and continue where you were. In ecommerce the cart was the perfect use. You could review, update and check out while still navigating the store. It was flexible, contextual and required no break in the journey.

We first implemented it in a concept site in 2017 and in 2018 I demoed a vision video to the execs at Nedbank showing how it could transform product interactions. From there I kept applying it to different products including EVO, Fluint and Healthbridge, adapting it to suit the context. These were not just experiments in isolation but features shipped into real products.

At the same time my instincts were being validated. Google and Microsoft were expanding their sidebars into multi tab utility panels, giving people everything from mail and calendar to tasks and notes in the same persistent space. They were proving at scale what I was already exploring in my own projects.

Of course resistance never went away. Many designers and product managers were uncomfortable because it broke the established patterns they were used to. My view was straightforward. If two of the largest online platforms in the world Gmail and Outlook could normalise the sidebar then we could too.

When OpenAI demoed their Atlas browser I was delighted to see them use a sidebar to enable live conversation with AI while browsing the web. This is the kind of potential I saw years ago.

One of my early visions was in the home loan journey. Imagine being midway through an application, getting stuck, and opening the sidebar to chat with support. Not only could they talk to you, they could also load the exact screen you were on in the left panel, so the help was directly contextual. At the time engineers gave me mixed feedback on whether that was technically feasible, but with advances in AI and contextual awareness it now feels within reach.

Looking back I was early in pushing this approach. Looking forward I believe it still holds huge value. A responsive content area on the left. A fixed width slide in sidebar on the right. It solves real problems, reduces friction and creates space for features exactly where you need them.

Living in the Maker’s Mind

I sometimes wonder why I am so detached from reality and why most of my mental space is occupied by things that seem impossible to do. Yet I am more comfortable in that headspace than I am in reality. While some people think of fantasy as dragons, castles, monsters, and mystery, for me fantasising is where I go to get into real technical detail.

AI is helping me refine this even more. I only get to talk it out and let it help me with research. I know there are tools out there that can visualise my thinking, but very few have the level of precision I hold in my mind. That makes using them frustrating because no tool yet allows me to fully visualise my endless ideas. I have to assume Elon Musk is like this except he has the money to build anything he can think of.

Like all things my ideas happen in waves. Sometimes I am exploring all manner of things, sometimes I am obsessing over just one, and other times I am not thinking of anything at all. I do not know if my ideas are good but they seem worth exploring and I can spend every free moment turning them over.

I am certain I am a visual thinker as Temple Grandin describes in her book. The more time I give myself to think free of life’s distractions the more detailed my thoughts become. I often imagine being asked to live in a house with everything I could ever want inside and I ask myself whether I could stay there for 100 days or even a year. Honestly I think I could. The isolation appeals to me. Of course I miss physical contact but I am able to go into monk mode quite easily and could certainly stay the course if the incentive was big enough.

I do get restless and I do switch gears but most of the time I am all in. Recently I have been working on a superyacht complete with its many structural details and aligned with a lifestyle philosophy woven into the branding. Then today I found myself thinking about the perfect desk setup and spent hours piecing together the most detailed configuration of a desk for someone like me. When I go deep I do not just think about its measurements and materials I think of all the different uses, the comfort and flexibility, the customisation. I am obsessed with the details.

This is not perfectionism. That comes much later in my process and often I never get that far. I simply do not have the means. I am convinced my mind is magical but I have little evidence for people to see. At best I sketch some things on paper. The design tools available to me together with my limited experience in using them make them not an option. AI might offer some hope but nothing available right now gives me what I need.

So the ideas remain in my head. At times it feels like an absolute waste. It can be frustrating and it can pull me into darker moods. I rarely show it but the truth is that I often feel down because I cannot bring what is in my head into reality.

Still I love the world in my mind. I can create all manner of things there far beyond what I make professionally or through the teams I lead. And I have come to realise this. Even if my ideas never fully exist in the real world they still shape the way I see it. They shape how I lead, how I create, and how I push at the boundaries of what is possible.

This is living in a maker’s mind.

Onboarding is everyone’s job

Strong onboarding does not start on day one, it begins the moment an offer is accepted and continues through the first ninety days. Handled well, it lowers anxiety for everyone, shortens the time to meaningful contribution, and shows what your standards look like in practice. Handled poorly, small frictions compound into doubt, momentum stalls, and a new colleague spends their early weeks decoding basics instead of learning the work.

A first day should never feel like a test of heroics. It is a test of preparation. The simple things matter because they set the tone for you as the new joiner and for the people welcoming you. Knowing exactly where to go, what time to arrive, where to park, which entrance to use, and what to bring tells you that someone has thought about you. If any of that is unclear, a short, upbeat email to your contact does two useful things at once. It gets the information you need and it nudges a busy team to close easy gaps they may have missed. Plan your route and arrive early for breathing room. When equipment and accounts land, test them immediately, keep a running list of names, acronyms, links, and open questions, and aim to ship something small in week one. A tidy pull request, a cleaned file structure, or a concise note that improves shared documentation is enough to create momentum, and momentum compounds.

From the team’s side, a joiner should feel like an upgrade, not an interruption. That feeling is created through coordination rather than cost. Meeting someone at the door beats a vague chat message to reception. A real tour shows where people actually work, where the quiet spaces are, how to book a room, and where to find help when no one is free. If you are handing over work, clean repos, folders, and permissions before the first walkthrough, and explain the decisions behind the structure rather than just pointing at it. Sit together for the first stand up to connect names with responsibilities and show where information lives. Be generous with time in week one, then widen scope as your new colleague settles. Think back to your own first day and close the gaps you wish had been closed for you.

Tone is set long before anyone arrives. Delegating coordination is wise, abdicating it is not. When groundwork is done early, day one feels calm and human. Equipment is ready, access granted, and the schedule breathes instead of racing from one introduction to the next. If you are the hiring manager, a short coffee in the diary on the morning of arrival tells the person that time with people matters as much as time with tools. Share why the team exists, how success is measured, and what good looks like over the first week, the first month, and the first ninety days. Early goals should anchor decisions without boxing anyone in. Where a probation period applies, make decisions early, communicate them clearly, and remove ambiguity so people can focus on doing their best work rather than reading the room.

Formal onboarding deserves a clear shape and cadence. Company orientation should cover vision, strategy, culture, security, the policies that protect people and customers, and the rhythms that keep the organisation running. Team and project onboarding should explain the roadmap, the stakeholders who shape it, the ways of working, the systems that carry the work, and the places where knowledge is stored. Keep the pace measured. Alternating short introductions with quiet time to set up and read will always beat a calendar packed with back to back meetings. If you are the one joining, use that space to surface questions. Curiosity is a sign of engagement, not a lack of it.

Familiar failures repeat across companies. The manager is missing on day one and the first impression is confusion. Laptops and licences arrive late, blocking everything else. No one meets the new colleague at the entrance, so a receptionist becomes a reluctant guide. Calendars are crammed in an effort to be helpful, and the person goes home knowing many names but understanding very little. None of these slips is dramatic on its own, yet together they send a message about what is valued. Get the basics right and trust is earned quickly. Miss them and the next few weeks are spent repairing avoidable damage.

Human touches still matter in a digital first world. If budget allows after the essentials, a simple welcome pack with a handwritten note, a few snacks, and something personal that shows you paid attention says far more about culture than an expensive swag box that tries to impress. Remote or hybrid teams can create the same spirit in different ways. Clear arrival emails with timezone friendly times, an always up to date onboarding page, a buddy who checks in daily during the first week, and a short end of day wrap listing what was set up and what is still pending will beat a beautiful office tour that a remote colleague never sees.

Onboarding is also a two way evaluation. The company is deciding whether the person is the right fit, and the person is deciding whether the company keeps its promises. When that mutual assessment is explicit, behaviour changes. Managers make themselves available, remove needless obstacles, and give timely feedback. Teams share context freely, invite participation early, and recognise small contributions that show understanding. If you are the new colleague, ask direct questions, document what you learn, and take ownership of a small slice of value quickly. When these habits line up, trust is built on day one and strengthened each week.

If you want a simple test for whether your approach is working, listen to how people describe the first fortnight. Do they talk about waiting, chasing, and guessing, or do they talk about learning, meeting, and doing. The words people reach for reveal the experience you actually delivered, not the one you intended. Fix the gaps that language exposes and the next onboarding will be better than the last.

Onboarding is the first proof of your culture. Treat it with care, make it warm and useful, and show up prepared and curious. Do this well and people begin contributing faster, make better decisions sooner, and carry confidence into the work that lasts long beyond day ninety.

If it would be helpful, let me know if I should share my onboarding checklist in a follow up post.

Moving On Professionally

You know it’s time to find a new job. The thought crosses your mind every morning as you open your laptop or walk into the office. You’re no longer happy where you are, but you’re not sure how to make the move.

Dissatisfaction rarely comes from a single reason. Work that once felt challenging no longer pushes you. You’re feeling overlooked and undervalued. The culture has shifted to the point that it doesn’t feel like your place anymore. Growth has stalled, or you’ve already reached the ceiling. Each of these on their own can be managed for a while, but when they come together the pressure builds. Leave it unchecked and sooner or later you’ll snap, whether that means walking away too quickly, losing your temper at the wrong time, or burning bridges you might need later. It’s always better to move before you reach that point.

Getting ready to leave starts well before you resign. Your CV needs to highlight what you achieved, not just the list of responsibilities you carried. Your portfolio should tell the story of your impact, not simply showcase outputs. Talking to a coach, mentor or trusted peer can help sharpen how you present yourself and give you clarity on your strengths. These steps prepare you so that when the right opportunity appears, you’re ready to step into it with confidence.

LinkedIn plays a bigger role than many people think. It isn’t only about recruiters. It’s a space where you can show your work, your perspective, and the way you think. Writing posts, joining conversations, and sharing what you’re working on helps you stay present in the minds of others. This isn’t about gaming the system or chasing likes. It’s about being visible, being likeable, and being the type of person people are happy to recommend when a role comes up. Most opportunities flow through people, not job boards, and if you’re never seen or heard, you’re forgotten when those conversations happen.

At the same time the fear of being found out is real. You picture colleagues noticing small changes on your profile. You worry your manager will catch wind of it and start making plans to replace you. That’s enough to stop many people from acting, but it doesn’t have to. LinkedIn has quiet settings that let recruiters see you without you announcing it to the world. You can reconnect with old colleagues and start conversations outside your company. You can balance what you post so it feels professional without raising suspicions. The key is to focus on building relationships, not just asking for a job when you need one.

When the time comes to move on, how you do it matters as much as the decision itself. Don’t burn bridges. Give proper notice and make sure the handover is done well. Respect the people you’ve worked with, even if the experience wasn’t always positive. Thank them for the time you shared, acknowledge what you learned, and give credit to those who supported you. Stay connected with colleagues after you leave. Never talk badly about your old company or the people in it. The way you exit will be remembered long after your role is forgotten, and it will follow you into future opportunities.

Moving on professionally isn’t only about getting a new job. It’s about building and protecting the reputation you carry with you. Be the type of person people would value working with again and again.

What DJs Taught Me About Valuing Design

When I was growing up most of my friends were DJs. For a moment I felt like I was rising as a designer in the same way, but it never quite turned out the same.

Let’s take a step back. When I say my friends were DJs, I’m talking about guys who were making me mix tapes that I took to boarding school with me. They later became headlining acts at Ultra. They came up playing every gig that would let them play, even if it meant no one on the dance floor and they played for 8 hours straight. Then later they were demanding insanely high salaries for playing one hour, because their name was bigger than the event itself.

Growing up with that, it felt normal for me to rise as a designer with aspirations of doing something similar. I certainly gained a name for myself, built a solid reputation, and increased my fees. But I never quite felt like I was the big name my friends were, and I never earned the type of money they could demand as the headline on the flyer I used to design for them.

I’ve had moderate career success and made some loot, but nothing close to what they charge for an hour of work. Some of them are flying around the world, at the promoter’s expense, stacking that international cheddar. I used to get frustrated when they would ask me to build their sites for less than they earned in an hour. What I didn’t always consider was that in their business that’s all they get. We don’t see the hours they put in for that one moment, never mind the weight their name carries, often far outweighing the event itself.

So do they make more per hour than I have? Certainly yes. But overall, I have managed to earn more hours. That doesn’t mean I have earned more. Let’s be clear: I have not. But their reputation and experience have compounded, and now they earn a fixed fee for that one hour. Something we all struggle to wrap our heads around, especially when we charge by the hour and literally put in the hours’ work.

Instead we should be thinking in terms of the value we bring. I’d go so far as to say you might want to trade the monthly retainer fee for a flat fee to do the job. Even if it takes you months, long term it could work out better financially if you invest correctly and pay yourself over time. A lesson I recently learned from Dan Mall.

And for our names carrying weight, maybe we need to start thinking of them as more than a well-designed logo. They need to be spoken about as our reputation, the same way a major brand leverages theirs. Designed by Craig.

I used to brand everything with Design by Digiguru or Made with love by Craig Jamieson.

I stopped doing this, at some point I got a little too modest to do it and focussed on other peoples brands. But maybe that’s a mistake. If you speak it, others will believe it, because you believe in yourself and the value you bring.

I want people to go: “It’s a CR—G.” Even when I don’t have my clever little logo on it, it’s in the quality of the work I do. So even if it’s for a big brand, people would still talk about the creative vision and excellence I bring.

Career Insurance

By the time you need professional help to land your next role, you will likely not be in a position to afford it. Most of us go it alone, never really considering that our situation can get that bad. Nobody wants to entertain that, until it does.

You probably will not say anything, because you will feel ashamed. This is a very normal way of feeling. You spend years propping yourself up, selling your best self, leveraging your job title, and believing that your worst day is as bad as it has ever been.

From what I am reading, unemployment is the highest it been in years amongst white collar tech employees. I do not know what black T-shirt wearing category that puts most creative types in, but it is fair to say many are struggling with the tech layoffs, global political and financial horror, and an industry identity crisis. I am brushing over this with a giant, lazy blanket statement about the poor state of the industry and assuming, like me, you are creative in one way or another. But this is not my point. It is something that could happen to anyone at any time.

Most people believe they will be safe in their job, regardless of how much they might dislike it. When that day comes that they are not, they try to manifest good things, because they are doing their best to stay positive and not be defeated by the challenges. You dust off the CV, try to figure out what work you might have saved to update the portfolio, and lean into your network for a new opportunity. Recruiters, job boards, freelance, side projects, there are so many things to try, and you do, but they still come up short. Not something someone with your years of experience wants to admit you are not very good at. But you never give up. You are just one more application away from that next opportunity, even if it is not a big one.

The savings get depleted. You are in fight or flight mode, trying to remain calm and keep up appearances, because you would not want to come off as desperate. Until you are. Then someone slides into your DMs, says schedule a call, which you do, and you sceptically and reluctantly entertain this sales pitch just in case. They know what they are doing, you feel seen, even if not heard, and then they hit you with their offer. But the problem is it is too late. You already cannot afford them. Parting ways with their fee, which is more than reasonable, is just something you cannot afford. Conventional wisdom would say you cannot afford not to. But when you are already leaning on family just to keep a roof over your head and have less money than you did as a broke teenager, it really is not something you can afford.

So you have no choice but to keep polishing your CV, applying for jobs, and waiting it out in the hope that something will give. You know if you just had enough money, they would be able to boost your career. Let us be honest, you are hoping they would and there are no guarantees. In fact, none of the very best advice really can.

It is the same with your health. I have seen many healthy people, obsessed with their well-chiselled six pack, tragically become ill or let themselves go, by no fault of their own. I have also seen unhealthy people who cannot find the motivation to take that first step to healing, so they remain overweight, in pain, and reaching out for that late night bag of crisps.

I cannot help most people stuck without a job or the means to afford professional help to secure their next role and get themselves out of financial ruin. But I can advise against believing it cannot happen to you. It has happened to me, on more than one occasion. I did nothing wrong. Just time and place. You do not have to make a mistake to learn from some of lifes tougher lessons.

So to anyone still in the good position to have a job, or unemployed with the financial means, speak to a professional who can help you position yourself should anything happen. That is part of job security. It is not only getting coaching in your current role, but investing in a future situation that hopefully never comes. It is not doomsday prepping, it is more like going to the gym three times a week. You might not have a perfect beach body, but you will be looking and feeling better than most people your age, and whether you can see it or not, building a foundation that will benefit you for years to come. Think of it as preventative care. We all know the benefits are much greater than trying to get treatment in an emergency.

If you are in the fortunate position to get professional help, take it. You don’t need a green open to work banner on your profile to need it. Get a coach, work on a maintenance plan to update your CV, actively engage with your network on LinkedIn, and keep your portfolio a little more current.

That is career insurance.