Every time I log into LinkedIn these days, I see another post about lay-offs, hiring freezes, and rescinded offers at another company.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:

  • That manager in your corner might be replaced by someone who gives you the Sunday Scaries before every Monday.
  • Your earning potential might be artificially capped no matter how hard you work to raise it.
  • You could be squeezed out of your role—demoted off the books—as collateral damage in petty office politics.  

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 just wanted a backlink and ended up the face of "younger Canadians facing a potential recession" on CP24, Toronto Star, The Financial Post, and Bloomberg BNN 😩

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.

7 Ways to Invest In Career Security (That No One Can Ever Take Away)

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.
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:

  1. Network authentically, not transactionally
  2. Always keep your own score
  3. Approach your career assets like a copywriter
  4. Invest in LinkedIn SEO
  5. Develop a freelance-friendly skill
  6. Distinguish yourself with side projects and ongoing education
  7. Learn to send a good cold email

1. Network authentically, not transactionally

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:

So many I've made a digital collage.

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?"

This was a fun little "campaign" that let me meet dozens of folks, from students to established entrepreneurs, while donating to my local food bank.

2. Keep your own score—in the points that matter to businesses

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.

Pink = content written by me and Blue = content produced by me through someone else.

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.

3. Make your impact POP! in your portfolio and resume

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.
This is why in my own portfolio I spell out the value I've created. It took me several hours to put together but now it's an asset I can use to sell myself when I need to.

4. Optimize your LinkedIn for relevant searches and first impressions

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:

  • What does a hiring manager type into the search bar to find someone like you? Is that language reflected in your headline, summary, experience, etc.? You can steal the language you see repeated across job postings.
  • Can you niche down in your positioning to trade irrelevant reach for deeper resonance with the right audience? I call myself a "B2B SaaS Content Marketer" because the best fit (and money) for me is tech companies selling to businesses.
  • Do you use the persuasive appeals of business—names, numbers, and needs? If you've worked with a big brand, were responsible for a measurable impact, or implemented a solution for the business, make it explicit. Specific outcomes are inherently more compelling than vague duties.
  • Scan your copy—does it impress in 10 seconds or less? Consider what your eye is drawn to first, second, third, etc., and give it something worth seeing.
I want employers and clients to know I'm both a writer and a marketer. I like to be my real self online (a bit silly) so I figure it's doubly important I show them real results.

5. Develop a marketable freelance skill

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:

  1. A marketable skill like landing page copywriting or recruiting (the more remote-friendly the better).
  2. An accounting/invoicing software like Quickbooks (paid), Freshbooks (paid), or Wave (free). Though you could use Google Sheets and Google Docs.
  3. A client willing to pay you (if you don't have a roster of existing clients, you can promote yourself to your network, or browse freelance job boards or use a marketplace like Upwork).

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.

6. Make time for ongoing education and side projects to expand what you can do

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.

How I Became an Instagram Poet (And Didn’t Even Know It)
It started as a joke and ended in 4k followers and $1600 in sales of an actual poetry book.

7. Learn how to send a good cold email

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:

  1. ClearBit Connect to find the email and social profiles for a contact at a particular company.
  2. StreakCRM for managing prospect research and outreach in my inbox (but you can use a spreadsheet).
It's easier to find Zuck's email than you'd think. Do they have email in the Metaverse yet?

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.

Career security gives you options

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.