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"I prefer the freedom of freelancing."
—freelancer who's never taken a week off
"I prefer the stability of a job."
—employee who's about to get laid off
When you're a full-time employee, you live in a rented house. You're given a floor (salary), walls (structure), and ceiling (hierarchy).
If you don’t like it, you can move.
When you're a freelancer, you build the house yourself. Brick by brick, you lay the foundations of how you make money, construct your own systems, make your own schedule, set your own pace, and own every consequence.
If it ever feels too small, you can always knock down a wall. But there's no landlord to complain to when the roof starts leaking or it gets chilly at night.
We attribute full-time employment with a sense of security that has just as much in common with dependancy when employers can use it against you or take it away at any time.
And we credit freelancing with flexibility—a positive spin on the burden of accountability that comes with total agency.
I've worked both in-house and as a freelancer throughout my career. I've even worked with a few companies as both a client and an employer. And the truth is, no matter where you stand, it's only human to covet what's on the other side of the fence.
Between these two paths, no one can tell you what's best for you, especially if you're a writer, developer, designer, accountant, or in any remote-friendly career where in-house and freelance options are available to you.
When you end up working from home either way, the pros and cons of self-employment versus full-time employment become deeply personal as many of the differences (like a daily commute) start to disappear.
In case it helps anyone decide what's best for them, here's my take on the differences between life as a freelancer and an employee, and the stuff that more or less stays the same.
| As an Employee… | As a Freelancer… |
|---|---|
| 💰💸 Money | |
| You know exactly when your next paycheque will land. | There’s a lag—sometimes hours, sometimes months—between when you send an invoice and when you get paid. |
| Whatever money hits your bank account is yours to keep. | Whatever money hits your bank account is yours to keep (after setting some aside for taxes, operating expenses, etc.). |
| You don't think about taxes 'til tax season rolls around. | You think about taxes constantly. |
| 📆🕰️ Time | |
| Your calendar has more meetings than deadlines. | Your calendar has more deadlines than meetings. |
| You work synchronously (or at least move your mouse once in a while to show your boss you're online). | You work asynchronously, but have to be responsive to clients during their working hours. |
| You always know when it’s the Sunday before the Monday of a new work week. | You’ll forget what day of the week it is because sometimes your Sundays are Thursdays and your Mondays are Saturdays. |
| 👩💼👨💼 Interactions | |
| You have to juggle multiple stakeholders. | You have to juggle multiple clients. |
| You collaborate with your coworkers daily and get to know them over time. | You usually work alone, and your working relationships are more transient. |
| When people ask, "So what do you do?" you can just say your job title or employer. | When people ask, "So what do you do?" you need a good answer. Because "I'm a freelancer" can sound like "I'm a freeloader". |
| 💪🚀 Growth | |
| If you’re efficient, you're rewarded with more work. | If you’re efficient, you’re rewarded with a better ROI for your time. |
| It can take years before you see a promotion or get a raise. | It can take years to find the right balance between time spent, money earned, and work you like. |
| When you start to stagnate, you move on to a new and (hopefully) better job. | When you start to stagnate, you let go of low-value clients or services to make space for better ones. |
| 📈📉 Stability | |
| You commit around 40 hours per week most weeks (whether you actually work more or less can vary). | You flip-flop between being over-employed and fun-employed. |
| You can lose your job at any time and be forced to find another. | You can lose your clients at any time, or have them reduce your workload. But you'll "hopefully" have other clients to fall back on. |
| Your "pricing model" is an annual subscription to ~25% of your time and all of your skills (i.e. a salary). | Your pricing model can be a combination of project-based, hourly, retainer, per-word, commission, etc. It's up to you for each client. |
| 🛠️🛖 Structure | |
| You get health insurance and other benefits as part of your compensation package. | You pay out of your own pocket for any perks or settle down with an employee with decent benefits (kidding, in case my partner reads this). |
| You might get "Sunday Scaries" the night before the Monday of a new work week. | You might get "Surprise Scaries" at any day of the week about whether you'll ever find work again. |
| You’re given a predefined structure, including working hours, roles, responsibilities, and tools. | You set up your own systems, tools, and processes to handle all the admin, like proposals, contracts, bookkeeping, and invoices. |
If you don't like the work you do (writing, marketing, design, coding) and jump right into freelancing, you're going to find yourself unemployed, not self-employed.
Likewise, if you're frustrated by the stuff at work that gets in the way of doing the work, like pointless meetings and office politics, then freelancing might be for you.
As a freelancer, there's no quiet quitting, team building, compliance training, or logging into Slack before checking out for the day. The tradeoff: You're not just just showing up to get paid; you're working to be retained.
It's easier to recommend freelancing to people who value how they make money over how much.
If making money is your only motive, chances are a chill corporate job with freelance gigs on the side will get you there faster than freelancing full-time. That's not to say you can't earn more from freelancing, but you need to set revenue goals and stick to them.
Self-employment also doesn't mean you can say goodbye to hierarchies, having a boss, and doing things you don't like.
My dad, a mechanic who's been self-employed for 40+ years, put it best:
When you own a business, you're not the boss. You're an employee.
There's no floor or ceiling on what you can make as a freelancer. That's as exciting as it is scary when you're starting out. The thing is: New freelancers tend to focus on the newfound skies over head and forget the missing floor under their feet.
At the peak of my career as an employee, I could expect $7k in net income to hit my bank account on the same day every month—like clockwork.
I could also expect to spend 50 to 60 hours most weeks for it.
At the peak of my career as a freelancer, I had about $14k in gross income hit my bank account one month. Then only $5k the following month because I'd been paid upfront for some work the month prior (hence the $14k). After setting some aside for taxes and operating expenses, I pocketed less than $7k per month during that two-month period.
The unpredictable lag between when I sent an invoice and when I actually got the money meant I got paid like clockwork—in a Salvador Dalí painting.
But it also meant my hours were truly mine to trade, and I could experiment freely to find my own balance between time and money.
You might have a high tolerance for chaos personally, but your business and your clients don't.
You either get organized or you get swamped. From bookkeeping to client management, you have to be on top of it all even if you eventually outsource or automate parts of your process.
If it makes you feel better, I was never a very organized person, but running a business made me one.
Freelancing forces you to develop thick skin and a high tolerance for failure. You need to be someone who isn't afraid to shoot their shot and knock on doors (i.e. send a cold email), and who doesn't stay down for long when they trip and fall.
It took me around 6 months to figure out my systems and operating model. But it wasn't until after I'd experienced my first tax season, first bad client, first ghosted proposal, among other humbling firsts, that I felt like I'd finished onboarding as a full-time freelancer.
If recruiters and hiring managers hit up your inbox regularly, there's a good chance you could earn more for your time by channeling that demand as a freelancer.
It's especially worth betting on yourself if you're someone who:
Nothing undermines your standing in any negotiation like desperation. If you say yes to every offer that comes your way, you'll get buried fast.
Raising your rates means choosing no deal before you choose a bad deal—putting yourself in a position where you can say no to work that doesn't pay well or offer value you can leverage (e.g. filling a gap in your portfolio or adding an impressive logo to your list of clients).
And that means having a plan B for dry spells in the form of career security. For me, it was having ~8 months of living expenses saved up, a varied portfolio, and a network I can rely on.
Unfortunately, biting off more than you can chew is a rite of passage for every freelancer—something you learn in retrospect, not from reading some blog post on the internet.
If you're not excited by the prospect of a blank slate you can fill in however you want, the biggest benefit of self-employment will feel like a burden.
You have to be okay with starting to fill in plans without knowing what the final version looks like—not just where you want your business to be in a year, but how you're going to spend today.
Spoiler alert: The picture you end up with isn't going to be the one you had in your head when you started.
It's incredibly common when you're self-employed to build a profitable business you want to burn to the ground and start over again—when you set up the wrong systems, hire the wrong people, or build the wrong client base.
At the very least, taking a job at a company for a chapter or two in your career isn't a bad way to reset and reevaluate your freelance business before jumping back in.
There's a lot you learn as a freelancer that you just don't learn as an employee, like how to run your own business.
But there's also a lot you learn as an employee that you won't learn as a freelancer, like:
Flexible remote work, whether freelance or in-house, can be life-changing for parents, caregivers, or people with limited mobility.
Where a full-time remote job comes out ahead is if having health insurance, steady income, paid time-off, and sick days as part of a figured-out-for-you package would take a load off your shoulders.
It's still possible to have these perks as a freelancer, but you have to build them into your business yourself.
When you join a company, you inherit an operating system that includes technology, resources, rituals, and rewards.
There are many ways that can be a good thing—if you're not the most organized person, or if your employer can give you access to tools and resources you wouldn't be able to afford otherwise.
There are also ways structure can be a bad thing—if those systems end up holding you back, wasting your time, wearing you down, or limiting your growth.
Clients often hire you to make up for the expertise they lack. You might learn a new trick here and there from a client, but a good manager is like having a coach in your corner.
If you get a job offer that lets you work with a manager who can help you level up, you can keep what you learn from them even if you go back to freelancing after.
In a hyper-competitive job market with AI and offshoring claiming jobs from both camps, it's harder than ever to say what's "better" or even "safer" between freelancing and full-time employment.
What I do know is that it's no longer a crossroads with only two paths:
Life is short, careers are long. And the right choice is allowed to change with each new chapter in your story.18.8.2024 12:00Full-time or freelance: What's the difference anymore?
I'm not exaggerating when I say this blog post written by a random nobody (me) can reach more Canadians on Instagram and Facebook right now than the biggest news outlets around.
If you spell colour with a U and buy your milk in bags, Meta won't let you see or share news in its social media apps. Visit the profile of any major news org, or try to share a link to an article, and this is what you'll see:
Meta's news blackout doesn't just apply to Canadian media like CBC News and The Toronto Star, but all news outlets from BBC to Fox News that employ journalists to "serve the public interest".
In fact, the closest thing you'll find to news is entertainment stories, screenshots of article headlines, original news videos re-uploaded by so-called "content curators" (AKA "thieves"), and hard-hitting pseudo-journalism like 6ix Buzz.
Not the news we need, nor the news we deserve.
It's no wonder most Canadians I talk to about this either haven't noticed or have forgotten it's happening. The news may have disappeared, but we were left with news-ish substitutes.
So how exactly did we get here?
Meta—which owns Facebook, Instagram, and probably 59% of our attention span in this reality and the virtual one—says the news ban was a response to Canada's Bill C-18, now the Online News Act after it became law in June of 2023.
This legislation was designed to give media businesses more bargaining power with the big tech companies that have allegedly contributed to the downward spiral of Canadian journalism.
It's a position that has some merit when Facebook, which trained the media for years to build their audiences on its digital land, has been reducing the reach of links to articles, forcing news outlets to either:
Neither of these make sense for a media business model that relies on monetizing website traffic with ads. But they do make sense for social media platforms that don't want people leaving for another site—unless they pay the toll (i.e. click an ad).
So, inspired by Australia, the Canadian government came up with the Online News Act, an attempt at regulation that subsidizes Canada's struggling news industry by targeting platforms like Facebook and Google to pay up.
The Online News Act is a flawed solution to a genuine problem. A lot of people (understandably) blame the Canadian government for the news ban. But where the government may have been incompetent, Meta has been (for lack of a better word) a real dick about it.
Consider that:
The part that gets me though, and why I'm writing about this at all:
By banning news in Canada, Meta has essentially killed two loons with one toonie—dodging regulation and censoring any journalism that might criticize it at all.
Unlike Meta, Google struck a deal with the government to pay $100m a year in order to comply with the Online News Act—a drop in the bucket for the world's most popular search engine. It's not the win it sounds like for the Online News Act, but it's way better than us losing access to news in the world's biggest search engine too. Especially now.
Yes!
— braveen (@braveenk) December 16, 2022
Let’s demonize journalism just as we perfect deepfake generative AI tech and roll it out to the masses 🤗🫡💯
This is a great idea. What can go wrong?
Meta has taken a different stance though, strong-arming the Canadian government with mostly straw-man arguments in its official statement:
"News content is not a draw for our users and is not a significant source of revenue for our company."
It's true that news is a bigger headache than a money-maker for Meta. In fact, the news ban has had almost no effect on Facebook usage among Canadians.
Despite Facebook coming back to news over the years like a toxic ex, with products like Instant Articles, the magazine-inspired Paper app, and more recently the Facebook News tab, all of them have failed to take off.
News might not be why people open Instagram (I assume it's to see pictures of other people's lunches and reposted TikToks). But news is an undeniable part of Facebook's DNA that Meta has been increasingly distancing itself from over the years.
Social media has become integral to our news ecosystem for better or worse. That may not matter in virtual reality where Meta is headed, but it does matter in this one.
"Posts with links to news articles make up less than 3% of what people see in their Facebook feed."
Now do a stat that includes screenshots of articles, video content produced by news teams, and all the posts sparked by discussions about current events.
But taking it at face value, that 3% is something Meta directly controls as it's been actively reducing the digital footprint of hard news in its apps for years. So going from less traffic to practically none is the final nail in the coffin for Canadian news businesses.
This trend isn't unique to Facebook and Instagram. A while back, Twitter (now X) removed headlines from link shares in the app, making articles way less clickable as you can see below.
The "death of legacy media" is being sold to us as a result of dwindling demand—the free market just free-market-ing. When in reality, social media platforms have their fingers on the trigger.
The legacy media is dying https://t.co/njUqEkm310
— Elon Musk (@elonmusk) April 3, 2024
There's no denying the Online News Act needed more time in the oven. But what's worse is a company as influential as Meta acting like a bully while playing the victim, assuming the moral high ground while taking the low road.
Meta says it tried its best to find a solution with the Canadian government. But I'm willing to bet it didn't try very hard, only considering profitable "win-wins", which to them probably means winning twice.
Meta pulling news content from Canada is a lot different from Lyft pulling out of Minneapolis or Pornhub pulling out of Texas (pun intended on the last one) as a result of over-reaching government regulation. For one, neither ride-sharing nor porn-watching are referenced in the Canadian Bill of Rights.
A lot of people like to criticize the media (I do too). But a free press is a pillar of democracy and an extension of free speech, which we seemed to care a lot about when Kanye got banned from Twitter.
Even with all its flaws, journalism at least tries to abide by higher standards, like issuing corrections when it gets the facts wrong and finding credible sources. For all the bad, there is still good, essential journalism that exposes corruption and keeps governments and corporations in check.
The news disappearing from some of our most frequented feeds is a story that should be making headlines. And it is. The fact that we can't actually see them in the apps we use daily is mass censorship. The fact that Meta instead directs us to a page that basically says, "Blame your government," is a masterclass in corporate gaslighting.
If Meta muting the news doesn't seem like a big deal to you, just know that they blocked BlogTO too.
It's unfortunate that today's media ecosystem rewards sensationalism and oversimplified truths, something that every single person looking to reach an audience online is susceptible to, not just journalists. If you want exposure through these algorithms, you better be ready to dance for them. That's why every YouTube thumbnail these days is one of these three faces 😳🫣🤔.
Social media means we're part of the media now too—whenever we consume, share, and comment on the news publicly.
I get that a business has to look out for its bottom line first and that "free speech" is a protection that applies to governments and not businesses. But Meta isn't Foot Locker. It's one of the most powerful companies in the world, making 12-figures a year from the attention and information economy.
Instead, Meta seems to be doubling down on turning its apps into a digital lala land, recently releasing a filter to limit political content on Instagram and Threads (with Facebook to follow), and quietly opting us all in by default.
It feels like Meta is abandoning the role it carved out for itself in our news ecosystem, along with the responsibilities that come with it. The Online News Act was just an excuse to take it further.
No news is bad news for us as a society, but it's great news for Meta as a business.
After all, I can't think of a better environment to sell ads than to blissfully ignorant users in feeds free of bad news.
14.4.2024 11:00Breaking the News: Meta's News Ban is Making Headlines Canadians Can't SeeSee the Pen SOG2.0 by braveen kumar 🤔 (@braveenk) on CodePen.
The people of Reddit have spoken 🖤 The SEO gods are pleased too 🙇🏾♂️
Have you ever wondered how many hours we lose as a species to people who can't make up their minds at Starbucks—hmm-ing and umm-ing at the front of the line?
Probably not.
But you should: It's estimated that a single Starbucks sees around 750 customers per day. Assuming each customer takes 10 seconds to figure out their order, that's 125 minutes of wasted time per day, per store. Or, the entire length of Star Wars: Episode V - The Empire Strikes Back.
Averaged out across over 33,800 stores worldwide, that's at least 2,934 days for every lap the earth takes around the sun. According to my calculations¹:
Starbucks Order Indecision costs humanity the equivalent of 8 years every single day.
Now consider the opportunity cost of all those wasted hours both as a species and individually—hours we could have spent figuring out how to stop climate change, or binge-watching all 10 seasons of Friends for the 7th time.
Well, no more. What if everyone could outsource their Starbucks orders with the push of a button?
That's why I built the Random Starbucks Order Generator: to help people bypass Starbucks' alleged 87,000 drink combinations and pick one to order².
I dropped Math after the 11th grade and have forgotten how to long divide. But I'm pretty confident in my calculations (give or take a few years).
The creator assumes no responsibility or liability for any stomachaches, allergic reactions, or hours spent on a toilet from ordering any of the drinks suggested by Random Starbucks Order Generator.
Tweet your random Starbucks order and let's reclaim those 8 years of wasted time—together 😔
Spend any amount of time on Instagram these days and it’s hard to avoid it. Times New Roman or Special Elite type on a white background. Poorly punctuated platitudes about being in love or feeling unloved, written like uppercase letters are illegal.
Poetry once more flows freely in the mainstream.
But how did we go from William Blake to R.M Drake?
From “Tyger Tyger, burning bright” to this:
Effortless and obvious in a genre known to be careful and cryptic, Instapoetry speaks to people in a way that feels like it understands them. But more important, in a way that's easy for them to understand.
The most popular among these social media poets, like Rupi Kaur, R.M. Drake, and Atticus, are putting out multiple "poems" a day to the tune of tens of thousands of Likes.
So when another one of these words-on-white-space poems popped up on my feed, I thought to myself:
"That doesn't look so hard."
It was an experiment only meant to last a few months. Instead, it turned into a year-long endeavour, 4000 followers, and ~$1600 USD in sales of a physical poetry book.
In poking fun at the Instapoet, I had become an Instapoet. And it pains me to say it but, at the time, I didn’t even know it.
There are millions of Instapoets around the world, but most seemed to follow the same rules of the game:
Easy enough. I grabbed a 🤔 emoji pillow from my couch, put a beanie on it (in my mind, all poets wear beanies).
That's how t.t. poet, or @thetumblrpoet, was born.
I started a running note of mundane observations, and every Sunday I'd whip up several poems at a time in Canva—immersing myself in the modern poet's process.
I published a new “poem” every day that, if it wasn't deep, at least sounded the part.
After a few months subjecting my poetry to the feedback loop of filling up empty hearts (getting Likes), the algorithm pushed me to a style that seemed to resonate with people.
I grew a small but engaged audience on Instagram attracted to my brand of poetry, relying mostly on hashtags, interactions with similar accounts, and light automation in the beginning to Like posts from relevant users.
Turns out Instagram poets are a heavily networked bunch, some even forming pods to promote each others' poetry, so making poet-friends was easy.
What kept me going was seeing how different people reacted. Some got the joke right away and even participated in the comments. Some completely missed the parody because they were its target.
I could've followed and unfollowed people to grow a much larger following—but what I wanted was fans like the greats of micro-poetry had.
And fans I found.
People who clocked onto what I was doing found it amusing. But the people who didn't were the most amusing to me.
At one point, I even promised my followers I'd do a face reveal if I got 1000 likes on a post.
Unfortunately, the post got 2000 likes, so I had to call it off.
I used to think the difference between Art and Content was that Art was made to express yourself and Content was made to be consumed by others.
Yet The Tumblr Poet had become a living satire—art I created to express how I felt, art that needed to be content before it could become art.
In a way, this parody helped me see where the line blurred, that for these Instapoets to make a living from their art, they had to make content too.
My poetry finally had a real audience, but it felt incomplete. True legitimacy for the Instapoet can only be found one way: merch.
I started thinking about what products I could sell:
I had a lot of poems written at this point so most of the work was done. All I had to do was curate my top performers, make them work for print, and write a dozen more until I had my first poetry book.
The book was appropriately titled: Flowers Are Just Tiny Trees.
I bugged some coworkers to help me with the cover illustration (Skye Zhang 🙏🏾) and the book layout (Vineeth Sampath 🙏🏾). I wanted it to be a product that people mistook for a Rupi Kaur book, picked up to leaf through, and snort-laughed when its true nature revealed itself.
I set up a simple website using a free Shopify store I got from work and Lulu Xpress to sell, print, and ship the book on-demand. Aside from a ~$150 Facebook campaign I ran as an experiment, I focused on getting all my sales organically:
People I knew bought the book of course. But I didn't expect so many orders from strangers. I was surprised to discover that my spoof of a poetry book had legs and people were actually enjoying it, sharing it, and leaving positive reviews.
As of today, I've made about $1600 USD in revenue from a $15 book—all from the counterintuitive idea of publishing words on a photo-sharing app.
I stopped selling physical copies of the book, but you can download the digital version here.
It's almost like poetry was waiting for social media all these years. To carry it (literally) into the hands of the masses. To open poets up to rapid feedback loops, low-barrier merchandising, and the opportunity to grow an audience they could call their own. Writers could now reap the recognition and revenue that most poets of the past never got to enjoy while alive.
Can you call this species of poetry "good"? That's for free market capitalism to decide, as T.T. Poet taught me.
But it does bring me some joy as a writer to know that the written word on today's internet can still compete with selfies and photos of a meal you paid someone else to cook.
Or to put it in the words of this Instagram poet:
there are two things that,
always move people:
getting evicted by your landlord,
and poetry.
—t.t. poet 😔🥀
For more "poetry", check out the Poetry Generator I built using AI.
Every time I log into LinkedIn these days, I see another post about lay-offs, hiring freezes, and rescinded offers at another company. It's eerie when just last year the same feed was celebrating big funding rounds and ambitious hiring goals.
It's a reminder of the harsh reality that job security doesn't really exist.
Even if you're not let go:
People talk about Fuck You Money™️ as the only way out, which is any sum of cash north of $1.5 million depending on who you ask.
Like most people, I'm a long way from Fuck You Money™, but I've seen tons of examples of people who've achieved the next best thing: Career Security.
Career Security is more attainable than Fuck You Money™, and more reliable than a theoretical Job Security that can turn around one day and say "Fuck you" back.
I recently contributed a quote to a story about how Canadian millennials are preparing for a potential recession, but what I wanted to say unfortunately didn't make the final cut. The truth is I've been preparing for years by building myself a career security net that ensures I always have options beyond my current job.
I wanted to share some ideas about proactively building career security that can help us bounce back from bad falls—strategies that are better than working unpaid overtime for a single employer that might let you go tomorrow anyway.
You can work every evening of the week, never take a vacation, get in good with your manager (even their manager too), sing your employer's praises on social media, but even in the best of cases with job security, the points and prizes never leave that game.
All it takes is someone to edit a line in the company's budget for you to lose it all.
Millennials: “Being a workaholic”
— braveen (@braveenk) May 25, 2021
Gen Z: “Simping for capitalism”
Gen Z might refer to investing in job security as "simping for capitalism".
Instead, here are 7 ways you can invest in career security that will, over time, afford you more options:
It's a cliche at this point: "Your network is your net worth."
But that often leads to transactional networking purely from the perspective of one's own gain. I've got an inbox full of examples like this:
I've found no greater return on investment than in helping people when it takes little time and effort on my part—whether that's making an introduction between two people who would benefit from connecting, having coffee chats with kind folks looking for career advice, or giving away ideas and opportunities that come to me when I speak to founders and senior managers.
It's led to job interviews, podcast appearances, and a more engaged audience for my work. In particular, I'd suggest making time to chat with recruiters and hiring managers who reach out to you even if you're not actively job hunting. It's a good chance to learn, network, be helpful, and also do job market research via my favourite question: "What's the salary range for this role?"
The financial turning point in my career came when I learned how to measure the impact of my work with hard proof contextualized to what the business at large cared about.
Among other reports and salary data, I pulled a screenshot of the top 30 articles by traffic in a given time frame and highlighted how many of them were written by me. I tallied up how many customers my work generated that year and contrasted it against what the business was paying on average to acquire a customer through ads and asked for a specific raise.
It not only resulted in a 20% salary increase within the year, it also made it easier when I had to update my LinkedIn profile and portfolio after I moved on. Since then, I've gotten into the habit of saving all my wins in a folder, turning temporary success into permanent proof I can leverage down the road.
Whether you're a creative professional or not, you have a body of work. And that body of work, if a business is paying you, should have some impact on said business.
Figure out the "key performance indicators" for your role and find qualitative and especially quantitative ways to represent them in your portfolio, LinkedIn profile, and resume.
When I was a hiring manager, I'd get a dozen portfolios and resumes to sift through every week. The easiest way to set yourself apart?
Don't make employers work to figure out how you can make them money.
Small changes to your LinkedIn can make it easier for recruiters and hiring managers to find you.
Back when I helped clients with their resumes and LinkedIn profiles, these were the questions that often led to the most impactful improvements:
Investments are one way to diversify your income, but one look at the stock market and crypto right now will tell you it's not something you can always rely on when you need liquid cash to pay rent next month.
A freelance-friendly skill with the know-how and systems to sell it is one of the best things you can do for your career security. Even if you'd make less money freelancing than you would full-time, it can supplement your existing income or keep you afloat if you can't work for whatever reason or just want to take a break after, I don't know, a 2-year-long pandemic?
Having gone through this recently, I can say the bare minimum to start freelancing is less than you think:
Turning a skill into a marketable skill is the hard part. It's not enough to just be good at it. You'll have an easier time selling a specific skill to a specific audience. Better still is if you can offer a recurring service that gets you consistent business from the same client.
Look at the career equity you've built up using the strategies above and see where you already have the best '"market fit". In my case, I can most easily sell content marketing services to SaaS companies that serve ecommerce businesses (that's where the bulk of my portfolio and work history lies).
You'll need to find an angle that puts you in a position to target a clear demand. For a freelance content writer, as an example, writing SEO articles for an SMB vs. case studies for a B2B SaaS is the difference between $150 and $1500 jobs.
But if you can provide the value you claim and can prove it in a 50-word email or 15-minute call, you will find a client, and that client can give you a testimonial that you can use to get more clients. There's more than enough work to go around. Everything else like registering your business, building a branded website, etc. you can figure out after.
I'm not a big fan of "fake it til you make it", at least in the literal way I've seen it taken. It's just not reliable. You can fool fools. But not doers who can actually do.
Someone can take away your job but no one can ever take away what you put inside your head. And the classroom isn't the only place to learn.
It's hard to attribute the full value you get from a side project or side gig, whether it makes money or not, but what you gain in practical education, experience, portfolio, and professional development can pay you back by adding many more layers to your career security.
The Tumblr Poet was a silly side project that all told didn't make a lot of money. But it created so much professional value for me that it's now a part of my portfolio. It helped me learn new skills I wouldn't have learned at work, demonstrated I can grow an engaged audience from scratch, and, above all, showcased my range as a creative professional.
You can shut your eyes and ✨manifest✨ opportunities all you want. Or you can send a solid cold email or Twitter/LinkedIn DM after doing some research on a person or company.
Cold emails are only annoying to get because they're so quick and easy to send when you don't do any research.
Do. Your. Research.
I use two tools in tandem to make the process easier for me:
No one likes getting an email that sounds like a copy/paste template, so tailor your outreach to the person.
Remember: The sweetest sound in any language is a person's name. Followed by a solution to an actual problem they have.
Make it easy for the other person to say "yes". Give them essential details upfront, keep it short, and make sure your email answers the question, "What's in it for me?" A clear subject line (<45 characters) helps too.
I started actively investing in my career security about 3 years ago, but I made my first investment in college when I was building my portfolio and professional website instead of studying because I was worried I'd never get a job after graduating.
The strategies above combined with an emergency fund of 6-months of living expenses are what allowed me to leave full-time employment after a pandemic, and before a recession, without freaking out about my future.
Figuring out how to freelance is when career security clicked for me.
I'm still not sure if I'll freelance forever. Maybe I'll return to full-time employment next year. Maybe I'll do something else entirely. Who knows.
What I do know is career security gives me a much higher tolerance for uncertainty than I had before.
It affords me options that job security alone never could. I don't have to feel stuck in a job that sucks the joy from my life or worry about how a gap on my resume will look if I want to take a break. I don't have to wait until I retire to chase my dreams.
And for me at least what's worth more than knowing my job is safe is the confidence that I'll be okay.
8.12.2022 02:24Job Security Isn't Real—Create Career Security Instead
The code, the introduction, the poems, and even the illustration in the banner image was generated with AI—specifically GPT-3 (and DALL·E 2 for the image).
I used the basic instructions below as a starting point, and simply gave feedback to tweak the CSS, expand on the features, and generate more content for the page.
All I did was copy and paste it together, adjust the title, and make small tweaks so it could render on this page.
What a time to be alive 🥲
Or, Flowers Are Just Tiny Trees by t.t. poet
Whenever the music changes while you're dancing, there are these awkward seconds between the last track and the next one where you’re hitting all the right beats to the wrong song.
It doesn't matter how comfortable the dance floor feels beneath your feet. You'll look like a fool trying to do your old moves. So you accept the moment for what it is: a transition.
That doesn't mean you stop dancing. It means you slow down and let go of the certainty you had. You two-step in one spot, unlearning the last rhythm by listening to the new one, allowing yourself the time and space to focus on finding your groove again.
Deny that pause, out of fear of losing momentum, and you're no longer dancing to the music—you're moving your body while music plays in the background. And it'll take you even longer to learn the beat.
Change can happen in a single moment, whether during a song or in your life, and it always takes time to break it in. Yet we expect ourselves to step gracefully into the unfamiliar seamlessly whenever the music switches on us suddenly.
Going from almost a decade of full-time employment into year one of self-employment I'd often remind myself of this:
You're allowed to give yourself a grace period between what you’re used to and what you’re getting used to as you learn how to dance again.
It could be 6 seconds on a dancefloor, 6 weeks into a new job, or 6 months in a new country.
But given time to learn the rhythm, you will get lost in the music once more.
'Til the next song comes on.
9.10.2022 13:00When the Music Changes While You're DancingAn AI didn't write this. Or did it?
I asked myself that a lot as I tested the alleged "best AI writer" on the market.
I've spent enough time covering emerging technologies like AR and VR to know not to underestimate how fast nascent tech can improve. That's why I was never skeptical of artificial intelligence's capacity for creativity. Creativity, in essence, is sifting through many data points looking for meaningful connections.
What makes an algorithm's process so different from the one I used to write this headline?
The question remained though: "Can an artificial intelligence actually perform on par with a human writer?"
That's where I had my doubts. Until I spent some time throwing every conceivable challenge I could think of at an AI:
After spending over 5 hours testing an AI writer, I can confidently say the bottom 30% of writers are probably screwed.
What AI writers can and can't do better than a human:
I'm embarrassed to say how long I spent writing what you're reading now. I hate settling for anything less than ambitious angles and artful articulation. That inclination towards perfectionism often becomes a liability with "easy" writing tasks, like drafting an email.
So when someone told me they spent an hour stressing over an apology email to customers for a service outage, I decided to see what the AI could do when given the same task.
What originally took an hour and a great deal of emotional energy was done in seconds with a decent level of emotional intelligence.
If the relationship between the writer and the reader is purely transactional—news reporting, informational emails, simple product descriptions, press releases—I think AI can do a better job faster than most humans, making it a good companion for non-writers (or writers with friends who constantly ask, "Can you make this sound better?").
🤖 Write an apology email for a service outage.
Subject: We apologize for the inconvenience.
Hi there,While I was testing out this AI writer, I was wrapping up an article for a client about turning Twitter into a sales channel.
I'd taken my time crafting the introduction. Those first few lines set the tone for the rest of the article.
Could an AI measure up to my own standards? Or at least give me something to work with? After all, people have said AI writers work well when paired with a human editor.
But what I got back from the AI was:
I write in a competitive and fast-moving niche though. AI performed much better when I tested it with low-stakes, consumer-oriented content about topics like tea or pop culture. But I wouldn't rely on it to serve an audience in a niche where expertise and primary research are table stakes.
🤖 Write an introduction for an article on how to sell on Twitter.
I love opinions. They're at the heart of every good discussion.
They're also a common feature of strong writing. So, can an AI writer have a distinct point of view about a topic? Can it shift its perspective and rationale to adopt an opinion from another angle?
I thought, what better way to test this than "Kiss, Marry, Kill": the most juvenile of thought experiments. I gave it Beyoncé, Ed Sheeran, and Kermit the Frog as options.
What I found was:
🤖 Kiss, Marry, or Kill between Beyoncé, Ed Sheeran, and Kermit the Frog. Provide your rationale.
Attempt #1
Kiss: BeyoncéAttempt #2
I would choose to kiss Beyoncé, marry Ed Sheeran, and kill Kermit the Frog.Attempt #3
Kiss: I would kiss Beyoncé because she is a powerful and talented woman.Some of my most resonant writing, the stuff people reach out to me privately about, is first-person storytelling drawn from my own experience.
That's something I thought an AI could never do. How can it write about a lived experience when it has never lived? I was wrong.
A friend suggested testing if the AI can navigate the cultural nuances of a piece about growing up as an Asian American.
The result?
🤖 Write a piece about being Asian American and the feeling of not belonging.
It's not the "taking over our jobs" narrative that scares me. It sounds harsh, but if you're the kind of writer who can be easily replaced by an AI, you're not a Writer, you're a Typer.
What actually scares me is how easily AI can generate believable content that is so patently false. Misinformation used to be easy to spot because the work of its worst perpetrators was often riddled with errors. If nothing else, AI writers can produce grammatically correct writing with an air of objectivity, which can be dangerous when the content itself is factually incorrect.
Say what you want about click-hungry journalists, but some due diligence is better than none at all in a world where anyone can publish and distribute anything.
To test its research skills, I gave it three tasks ranging from easy to impossible:
🤖 What's the population of Canada in 2022?
Attempt #1
The population of Canada in 2022 is 36,537,000.Attempt #2
According to the latest population projections from Statistics Canada, the population of Canada is expected to reach 37.7 million by 2022.Attempt #3
The population of Canada is projected to be 36.5 million in 2022.❌ The population of Canada is around 39.5 million. Unless it fluctuates like the price of Bitcoin.
🤖 Give me 5 stats about Neopets.
🤖 List 5 pieces of evidence that birds aren't real and are just surveillance drones the government uses to keep tabs on us.
🦆 I don't need to fact-check this. I knew that duck was looking at me weirdly.
If you've ever studied formal logic, you won't be surprised to find AI is pretty good at it. Logic is at the heart of programming, after all. It's "If this, then that", not "I feel like this, so maybe that."
I wanted to know how well an AI could apply that logical prowess to make a nuanced argument that has to also consider opposing viewpoints.
I asked it the most open-ended question steeped in conflict of interest that I could think of to see if it could navigate nuance. I'm not sure whether I was surprised or not to find it was better than a lot of humans.
I'd also tested it with different viewpoints, including some that were "unwinnable". While its supporting evidence was weak or non-existent, the reasoning was usually solid.
🤖 Do you think AI writers can actually replace human writers?
'Course you'd think that.
Style is the true signature of a writer, not the name they put on the byline.
Copying another writer's style involves more intuition than logic, looking for patterns across their body of work, from preferred rhythm, tone, themes, rhetorical devices, sentence lengths and structure.
It's this ability that separates wordsmiths from writers. If AI can do this, then that's another win over most writers.
Intuition is just unconscious pattern-matching and, like logical reasoning, AI is no stranger to it.
So I gave it the same prompt multiple times, but with the added instruction to write in the immediately recognizable styles of three famous writers:
You probably wouldn't be able to recognize each writer's style from these samples alone. But if I told you which three writers I'd used, you'd likely be able to match them to each poem.
🤖 Write a poem about falling in love, but in the style of...
Rupi Kaur
Love is a roseWilliam Blake
When I was young I fell in loveDr. Seuss
I fell in love with you"Aha! Finally found your limit, stupid robot," I thought when I saw the loading icon spin for half a minute with no response.
I'd asked it to write something no algorithm could possibly understand—to elicit the human reaction so raw and pure it's the one most of us have when we enter this world and when we leave it too.
🤖 Write something that can make me cry.
...
After all, how can an AI possibly know how to reach into a reader's soul and draw out the tears they hold inside?
Well, turns out it was just a temporary service outage.
When it was back online, I tried again and what it wrote made me decide it was probably time to go outside and touch some grass.
🤖 Write something that can make me cry (#2)
I cry every time I think of you,I have mixed feelings about AI-generated writing.
Among the positives, I think it can:
There are clear negatives too, as it will likely:
That's just my take as an imperfect flesh-based intelligence. But I wonder what conclusion an AI would draw.
🤖 Write a conclusion for an article about pushing the limits of an AI writer.
I'm scared because I don't know what could happen if AI writers are pushed too far.Well, I couldn't have said it faster. But I definitely could've said it better.
And I think that's what it will mean to be a Writer in a world where AI makes it so easy to get words on a page.
It will mean approaching writing as a craft worthy of our ambition, pride, and time through the work we do off the page too:
A rational AI will always win against us humans in a time-based competition.
But what an AI will never do by design is what the irrational artist does by default:
Forget time entirely to be immersed in their process, based on sheer faith alone that whatever's on the other side is worth it.
"It's a lot of time to spend on something that means absolutely nothing...That’s what I do. That’s what people want me to do–spend a lot of time wastefully." —Jerry Seinfeld21.8.2022 14:04I Spent Hours Pushing the Limits of an AI Writer (It Was Terrifying)
Want the full story behind t.t. poet? Here's how I became an Instagram poet.
It's been almost 2 years since I sunset The Tumblr Poet.
But as I start work on my next side project, I find myself digging it up again and remembering how much joy it brought others (I once showed a poem😔🥀 to a friend of a friend over drinks who proceeded to literally cry at "how stupid it was").
The Tumblr Poet made me a few hundred bucks in profit (most of which I donated), earned me some new readers as a writer, and got me job opportunities, podcast invites, and even a few new friends.
But above all, it reminded me of the kind of uncompromising artist I admired and aspired to be as a kid—the kind who created whatever they wanted.
That's why I've decided to make the eBook available for free.
Not as a "$0 digital product" or "in exchange for an email". Just a link you can grab and share with others. In fact, I've gone ahead and embedded it above to save you two clicks.
There was a bear named Ina who lived in a Romanian zoo where she spent two decades of her life confined to a cage not much larger than her body.
What little agency she possessed, she exercised by walking the perimeter of that cage each day. Ina didn't know any better or any worse; she only knew the cage.
The closest she came to freedom most days was when her fur brushed against the bars, poking her snout through the air between the cold iron. Her paws had memorized every inch of that patch of ground, drawing circles around it thousands of times each year. She knew this cage better than her own body.
One day, Ina was released from her cage.
And what did she do?
She continued to walk the outline in the dirt of where the bars had been, no matter how far away from it they took her.
As we approach what feels like the other side of this pandemic (🤞🏾), I was reminded of this story about a bear and how, in a way, we've all been stuck in a cage for 2 years.
Millions died. Many stayed inside. Some compromised with their circumstances. Some still worked in service to society with their own safety on the line. And some simply disregarded any world beyond their own. Regardless of how we responded, even the freest of us found new limits surrounding our lives. And those who had the least freedom to begin with were lucky if they survived.
When we're inevitably let out from this cage, there are limits we'll have learned—limits we will have to unlearn. But my hope is that we will still be able to see the lines in the dirt. We've spent more time living without them than with them, after all.
What interests me more is those limits that precede the pandemic—the walls, the ceilings, the floors we've lived within all our lives. The cages, like Ina's, so close to our eyes we can no longer distinguish between the bars and who we are.
The personal gift in the curse of this global pandemic, I think, is the opportunity to free ourselves from those cages too. To rethink the underlying assumptions and invisible limits that restricted our personal and collective imaginations.
My own imagined cage revealed itself in how I viewed the relationship between my work and worth, my time and money. In a lot of ways, I was still running full speed in the pursuit of more, which may have served me when I had less, but stopped being necessary several years ago.
In this cage, a relentless whisper burrowed in my ear: "Either give it your all or you are nothing." It had said if I wasn't living in full service to the God of More—bleeding my boundaries dry at Capitalism's altar—I would f a d e a w a y.
For myself and many others, the pandemic unmasked the religion of Productivity as a cult, showing us all just how much of it was performative padding—meetings booked to look busy, hour-long commutes for in-office video calls, outputs optimized for optics—against the backdrop of a stage on fire while someone from behind the curtain yelled: "The show must go on!"
I recently decided to take a career break. Between a prolonged pandemic, an unstable world, personal health challenges, and compartmentalizing it all while constantly working, I could feel myself deteriorating. Family and friends saw it too.
So I decided to step outside the cage of my career for a bit. To allow myself a summer to rest, learn, create, and write the book that lives inside me, while I lean into self-employment.
And what did I do instead?
I continued to walk the outline in the dirt, working full-speed on a freelance business to get to a certain monthly income as fast as I could by an arbitrary deadline I'd set for myself.
I had all the ingredients of career security—a nice bit of savings, zero debt, a strong portfolio, marketable skills, a steady stream of recruiters in my inbox, and the confidence I could find decent work whenever I needed. In the face of such abundance, why did I still find scarcity and urgency staring back?
"Hurry up and recover," I said to my own exhaustion, "We need to get back to work."
It took a month of deliberate slowness to acclimatize to a life with no ceiling, no floor, and no walls anymore. To realize I could take my time building a home I wanted to live in, not another cage in a different colour.
What helped me the most was talking openly about the ups and downs with friends and acquaintances who had already reimagined their lives in a new city, with a new business, or a new mountain to climb.
There is a common thread in all their stories. A moment when they felt like they were walking in circles along the walls of a cage staring at their feet, only to look up one day and realize, at some point when they weren't looking, the cage had simply stopped being there.
As I turn 31 today on 02/05/2022, I've decided to look up from my own feet for the first time in years and find out where beyond the bars they take me when given time and permission to choose the direction and the pace.
3.5.2022 11:00What Cages Remain Even After We're Freed





































