The clean career story is usually bullshit, but the first slap is useful

Most design career stories get cleaned up after the fact.

Which makes sense. Nobody wants to write the honest version on LinkedIn.

I tried one thing. It didn’t work. I thought I was good. The job market disagreed. I took whatever got me in the door. I struggled at the first real task. I got promoted by accident because the senior person left. I stayed too long. I left for a reason that sounds dumb now. I ignored some red flags. I got let go. Then I got let go again. Then I had to pretend I was normal on interviews while internally doing a full forensic audit on every company website, Glassdoor review, founder podcast, and weird little sentence that sounded too polished.

That is not as nice as the sanitized bullshit version:

Started in design. Grew into product. Learned a lot. Grateful for the journey.

Cute.

My version started with trying to get into 2D and 3D animation. I took a trade program here in Montreal and, honestly, I thought I was good because school kept telling me I was good. Art was always the thing I could do. I got good grades. I had confidence. I had that very useful early-twenties disease where you think talent is going to organize your life for you. Cute little idiot era.

Then I tried to get a job.

Nothing.

Not even an internship. No dramatic rejection. No villain speech. Just the market quietly ignoring me while I sat there with my little portfolio wondering why the universe had not noticed my obvious genius.

That was the first real slap.

The market did not give a shit about my art school confidence.

School confidence and market confidence are not the same thing.

School can tell you you are good inside the rules of school. The market tells you whether anyone wants the thing you are selling. It is much colder. It is much less encouraging. It does not care that your teacher liked your final project. It does not care that you were the artsy kid in high school. It does not care that you can make something pretty in Photoshop while listening to sad music and feeling important.

The market just sits there like, cool, but can this person help me make money, save time, reduce risk, explain something, sell something, build something, fix something, or make this less of a flaming pile of operational garbage?

That was annoying to learn.

Also useful.

So I went back. Graphic design. Web design. HTML. CSS. JavaScript. PHP. The boring parts. The useful parts. The shit that actually made me employable. And this time I treated it differently. I went into monk mode, not in a cute productivity YouTube way. More in a I already watched one version of my plan die and I am not doing that shit again way.

That messy path is also why portfolio work is so hard to explain later. The real story is rarely clean, but the story still needs to make sense. That is one of the things we look for in a Design Table Audit, because sometimes the problem is not your experience. It is that your experience reads like a junk drawer with nice typography.

Getting humbled got me back into the building.

But the first job taught me something worse.

Feedback does not always sound like feedback.

Feedback does not always sound like feedback

Eventually I got my first real design job.

I was excited. I had officially made it. I was a professional designer, which mostly meant I now got paid to be confused in a different building.

One of my first tasks was making Google ads.

I was bad at it.

Not fake humble bad. Actually bad. I kept looking at what the previous designer had done and trying to copy the style with my own little twist. Very junior. Very logical. Very not working.

Nothing was landing.

Then the CEO came in and asked if I liked my job.

Which sounds harmless if you are reading it on a screen.

It was not harmless.

My body understood the sentence before my brain did. He was not asking if I liked my job. He was asking why the work sucked without saying why does the work suck.

That is one of those moments school does not prepare you for. Nobody gives you a nice rubric for indirect disappointment. Nobody says, hey, when a CEO casually asks if you like your job one month in, that might not be a wellness check.

So I stopped copying what was already there.

I started looking outside the company. Other e-commerce brands. Other ads. Other ways people were selling. Other patterns. Other ways the work could actually perform.

That was the shift.

I stopped treating design like matching the existing style was the whole job.

Fitting in is not the same as doing good work. Sometimes fitting in just means you are recreating the same average shit with slightly different shadows.

That moment stayed with me because it taught me something I still believe now: design is not just making something that belongs in the file. It has to belong in the business.

That lesson helped me survive the first job.

The next lesson made me leave it.

Sometimes a good job is still training you for yesterday

This week on The Design Table Podcast, Nick interviewed me about my 16-year path through design.

Not the polished version.

The actual version. The one with bad timing, dumb confidence, questionable decisions, and a few useful scars.

Animation school. Trade programs. Mailing resumes like it was the Stone Age. Coding landing pages. Learning Google ads by making a bunch of bad ones first. Becoming the only designer way too early. Asking for more money before I really understood what I was worth. Leaving a stable job because I wanted to learn CSS3.

Which still sounds ridiculous.

But at the time, it felt like watching the industry leave without me.

I had been at my first real design job for four and a half years. I knew the product. I knew the codebase. I knew the weird old browser problems that slowly remove years from your life. The company wanted me to stay. They offered more money.

And I still left.

Not because the job was horrible. It wasn’t. The business was making money. The product worked. The rational thing was probably to take the money and keep going like a responsible adult with fewer delusions and a functioning relationship with reality.

But I could feel myself getting stale.

That is a weird thing to explain, because from the outside it looks like stability. Stable job. Stable product. Stable income. Good little designer. Keep going.

But sometimes comfort is just skill decay with a better outfit.

That sounds dramatic, but it is real.

The market was moving. HTML5. CSS3. New ways of building. New expectations. Meanwhile, my day-to-day work was training me for a version of the industry that was starting to expire.

That is a different kind of career risk.

It does not look like risk until later.

And this is why the AI conversation feels familiar. Different tools. Same feeling. Back then it was CSS3 and HTML5. Now it is AI, Cursor, vibe coding, designers opening PRs, product teams asking for prototypes that behave more like software and less like museum exhibits inside Figma.

I do not think every designer needs to become an engineer.

But I do think every designer needs to notice when their workflow is quietly training them for yesterday.

That is the dangerous part.

Not being behind.

Not noticing you are becoming behind.

That feeling made me leave a job that looked fine on paper.

Later, I learned the opposite problem exists too.

Some jobs look fine on paper and are quietly on fire.

Red flags usually show up before the fire, but you still have to believe them

Another part of the episode that stuck out when I listened back was how many times the warning signs were already there.

At one company, I started to mistrust the CEO. Things felt shady. Not in a dramatic movie way. More in a why does this smell like poo and why is everyone pretending we are in a candle store way.

I left.

A year later the company shut down for the exact reasons I suspected.

That is a weird feeling. You do not want to be right about that stuff, but you also kind of want to high-five your past self for getting out before the floor collapsed.

Then later I joined another company where the VP of Product hired me.

Five days in, he quit.

Five days.

That is not a red flag.

That is a red flag wearing another red flag as a cape.

Then a bunch of other people left. Then the CEO started calling me a product person. Then I was being asked to talk about features in a way that made them sound more done than they were.

That is when you realize company risk is not some abstract thing investors talk about in quarterly updates.

It lands on your desk.

It becomes your Figma file.

It becomes the sales promise you are now trying to make real.

It becomes the weird sentence you are asked to say in a user interview even though every cell in your body is going, this is bullshit.

Your job is not only to evaluate the role.

Your job is to evaluate the company’s relationship with reality.

That might be one of the most useful career skills I have picked up.

Can this company tell the truth about where the product is?

Can leadership separate ambition from fantasy?

Are people allowed to say this is not ready?

Does the team know what is actually being sold?

Because if the answer is no, congratulations, you are not joining a company.

You are joining a cleanup crew with a laptop.

I learned that lesson once by leaving before the floor collapsed.

Then I learned it again the harder way.

Getting let go twice changed how I read every room

The first time, I was angry.

I had been there for four years. Helped ship the product. Helped grow it. Built trust with engineering. Did the work. Then the meeting invite showed up with HR on it.

You know that meeting.

Laptop shut off a few minutes later. Access gone. Years of work reduced to a calendar invite and a polite sentence about going in a different direction. The corporate version of taking your lunch tray, kicking you out of the cafeteria, and telling you to have a nice day.

That one pissed me off.

The second one was different.

Seven months later, I got let go again. Different company. Different excuse. Same result.

That one made me question if I was the problem, which is a fun little mental carnival nobody asks to attend. Just a full circus of bullshit in my head.

And that is the part people usually clean up in the career story.

They talk about resilience after they have recovered. They talk about growth after the next title lands. They talk about the lesson once the scar is old enough to become content.

But in the actual moment, it does not feel like growth.

It feels like your confidence leaving the room before you do.

The arrogant version of me was gone. The same guy who once walked out of a meeting and asked for a $15,000 raise on the spot did not exist anymore.

After that, I stopped interviewing like someone hoping to be picked.

I started interviewing like someone looking for smoke, lies, and whatever weird smell is coming from the basement.

Founder background. Glassdoor. Company history. Product quality. Weird answers. Rehearsed optimism. How long people stayed. How people talked about the team. Whether the story sounded too clean.

I was not jumping into another sinking ship just because someone painted the deck chairs a nice shade of startup blue.

That is another thing layoffs change.

They do not just hurt your confidence.

They change your risk model.

Before that, I thought a lot about whether I was good enough for the company. After that, I started thinking a lot more about whether the company was sane enough for me.

That shift matters.

Because being hired by the wrong company still feels like being chosen at the beginning. Then six months later you realize you were not chosen. You were recruited into a fire drill.

That is the unsexy part of experience.

Bad moments do not automatically make you wiser.

You have to actually look at them.

The scars only matter if they turn into pattern recognition

I do not think experience automatically makes you better.

Some people repeat the same year ten times and call it seniority. Very brave. Very LinkedIn. Very please-end-this-meeting.

But a messy career can give you pattern recognition if you are willing to look at it honestly.

You start to notice when the room is avoiding the real problem. You start to hear the difference between a company with ambition and a company selling panic with nicer slides. You start to know when feedback is actually feedback, and when it is a warning shot dressed up as a harmless question.

You also start to understand that design is not just craft.

It is judgment.

Judgment about where the product is going. Judgment about whether the work matters. Judgment about whether the company can actually support the thing it says it wants to build. Judgment about whether you are growing, or just getting better at surviving the same old mess.

That is the thinking behind the Product Design Blueprint. At some point the job is not just making better screens. It is knowing which decisions actually move adoption, retention, and revenue.

That is why this episode matters to me.

It is not a neat story about becoming a principal product designer. That would be boring, and also mostly fake.

It is about the ugly middle. The duct tape part. The mild panic part. The part where you are trying to stay useful while the industry keeps changing its clothes every few years.

Web design becomes UI/UX. UI/UX becomes product design. Designers stop coding. Then suddenly everyone is talking about designers opening PRs again. AI shows up. Vibe coding shows up. The builder-designer starts looking less like a weird hybrid and more like someone who accidentally kept the right muscle alive.

The tools change. The titles change. The job market changes.

You have to keep changing too, without becoming the person who chases every shiny object like a golden retriever in a productivity seminar.

And honestly, that gets harder when you are doing it alone inside your own head, which is part of why we started the UX and Product Design Community. Not because everyone needs another Slack group to ignore, but because sometimes you need other designers around you who can say, yeah, that is a real problem, and no, you are not insane.

That is the real reason I think this episode is worth watching.

Not because it is a clean career map.

Because it is the opposite.

Watch this if your career has not been the clean version

Watch the episode.

Not because my career path is special. It is probably more normal than the clean version people keep pretending is normal.

The clean version is usually just the messy version with better lighting and all the shit parts edited out, which is basically LinkedIn’s entire business model.

If you are early in your career, this episode will show you that getting humbled does not mean you are done. If you are mid-career, it will probably hit the part of you that wonders whether you are still growing or just maintaining. If you are senior, it might make you think about how many of your strongest instincts came from the parts of your career you would never put in a promotion announcement.

And if you have been laid off, burned by a weird company, stuck in a role that made you stale, or quietly wondering if the industry is moving without you, this one will probably feel familiar.

Not motivational.

Familiar.

A little uncomfortable.

Probably more useful.

Watch the full episode here.

Till next week,