Why You Need a Side Gig

Welcome to the first edition of Side Gig Hacks!

Every week, I’ll send you actionable tips about how to create, publish, and market profitable digital products on the side.

But first, a quick backstory.

One year ago, I was laid off from my job.

Surprisingly, I didn’t panic. Instead, I felt a sense of relief.

Not because I hated my job—far from it. I actually loved what I did.

I was a senior executive leading a team of 150+ employees and genuinely enjoyed being a leader. My boss was one of the best I’d ever worked for, and I had a lot of autonomy. I also contributed to solid financial results for the company.

When people asked if I was shocked, my answer was: “Yes, in the micro, but not in the macro.”

In that particular role, at that specific time, and in that environment, I didn’t see it coming. So in the micro, it was a shock.

However, in the macro, I wasn't surprised at all.

In fact, I 100% expected it.

I knew there was a good chance this would happen to me at some point in my career.

I had no idea about what role or what company I'd be working for when I got laid off, but I've witnessed so many “Turkey before Thanksgiving” stories that I just knew it was statistically inevitable.

There are so many factors that could affect a seemingly stable job (economy, business strategy, politics, etc.) and most are out of anyone's control.

In fact, I was so convinced that getting laid off was bound to happen that I had been actively preparing for it for years.

How? By starting side gigs.

Here are a few things I did while having different jobs:

• Wrote books

• Published courses

• Created digital products

• Ran live webinars

• Delivered cohort-based courses

• Coached & mentored others

• Gave professional talks

And I got paid to do all of it.

The biggest return wasn't a financial one though. It was the skills I gained in learning how to do those tasks.

Today, I have published 20+ books (9 Amazon bestsellers) with 120,000+ readers. I’ve also launched 15+ courses on Udemy with 420,000+ students.

Along the way, I learned everything from persuasive writing to search optimization to psychological triggers.

I also learned how to use a ton of new tools—everything from design software to email platforms—that helped me automate my side projects.

All of those skills can be applied to any future venture.

Why did I start those side businesses?

I was primarily driven by passion. I really enjoy learning, writing, teaching, and creating.

But there was another motivator too: fear.

Fear of potentially losing my job and then having to figure out all this stuff when I didn't have the luxury of time.

Here are a few other things I did to plan ahead:

• Started an LLC

• Bought life & disability insurance (independent of employers)

• Hired a Virtual Assistant (VA)

• Hired a professional tax & accounting company

The relief I felt after getting laid off was probably due to the fact that I knew I had a system in place to rely on in case this ever happened.

In other words, side gigs saved me.

Will I ever apply for another full-time job?

The short answer is I don't know.

I never hated being employed. I realize I'm in the minority here (maybe because I've had a lucky streak of good companies, roles, and leaders in the past). So I might be open to getting another job later. However, what I can say is that since getting laid off, the thought of applying to a new job doesn’t excite me that much.

The bottom line for my decision would be this: I have a family to take care of, and providing for them will be the primary deciding factor about what I'll do in the future.

What did I do since getting laid off?

In short: more side gigs.

Immediately after I got laid off, I felt like I needed to go all-in on one thing by starting my own business. However, I quickly realized that it was better for me to continue to build small projects and services instead of putting all my eggs in one basket.

Here are a few things I did:

• Freelanced as a strategy & operations consultant (my biggest client was Microsoft)

• Launched a live $1,500 cohort-based course (recently finished the fourth cohort)

• Published two online courses on Udemy (about ChatGPT)

• Started two newsletters (one called AI for Leaders and another called Leadership 80/20)

• Launched a third newsletter (the one you’re reading now)

What am I working on now?

• Speaking/ training at organizations (this pays really well but is very sporadic)

• Writing two new books and publishing another Udemy course (specifically about AI & Change Management)

• Growing my 3 newsletters (I love the newsletter business model & I’m experimenting with paid ads on Facebook)

• Continuing to offer strategy consulting engagements (on a limited basis - depending on the opportunity)

What I am experimenting with/ potentially launching

• Crafting a $10,000 1:1 coaching offer (this would be my most expensive B2C package for select clients)

• Focusing more on video (YouTube/ TikTok/ Instagram short-form content)

• Launching another podcast (something related to leadership/ management)

I’ll continue to experiment and build small projects.

Why you need a side gig

Here’s the reality: jobs aren’t getting safer.

AI is advancing fast, and layoffs will only increase.

Your best protection is taking control and building something of your own.

And a side gig is like an insurance policy for your career.

It gives you financial stability, helps you learn valuable skills, and makes you resilient when uncertainty strikes.

You don’t have to quit your job tomorrow or take huge risks. You can start small and grow steadily. That's exactly why I started Side Gig Hacks. To share all those tips with you.

Stay tuned for more.

Hassan