4 Questions To Ask Yourself Before Quitting Your Job for Your Side Hustle

Make sure of these things before pursuing your passion full-time.

4 Questions To Ask Yourself Before Quitting Your Job for Your Side Hustle
Anangsha Alammyan on Instagram

Make sure of these things before pursuing your passion full-time.

It’s not easy to quit a high-paying and secure job for something that might soar over the moon one day and go up in flames the next.

What if you wake up one day with no passion left to make it last? What if your income streams dry up? And worst of all, what if everyone who’s been warning you is right?

I know. The future is uncertain and the plunge is not easy.

I’ve been pondering over quitting my job since September 2020, and haven’t yet fully achieved the “self-employed” status. I’ve journaled through hundreds of pages, worked on expense trackers and tax plans, and even then, it took me eight months to finally take a leap of faith.

Sure, you might not be an overthinker like me, but there are some questions I believe every person should ponder over before quitting their job and pursuing their side hustle full-time. In this post, I’m discussing the four most important questions that changed my perspective and will help you as well.

1. Do I depend only on one income source?

This is the first question my self-employed friends asked me to consider before quitting my job. As a freelancer, it’s important that you build multiple streams of income for yourself. That way, even if one dries up, you can still rely on the rest until you figure out a way to rebuild what you’ve lost.

Since I’m a writer, here are the income streams that sustain me (for now):

  • Freelance writing.
  • Consulting for writing, editing, and publishing-related queries.
  • Brand journalism and paid collaborations.
  • Writing on Medium and News Break.
  • Building my digital product.

Here are some ways I plan to expand the income streams further in the coming months:

  • Find more freelance clients.
  • Build a proofreading and editing service.
  • Monetize my newsletter.

And more. There will always be more. The sky, as they say, is the limit.

2. Do I have an emergency fund?

Life as a freelancer isn’t a cakewalk. Most self-employed people live from paycheck-to-paycheck, at least in the beginning. To quit your cushy job, make sure you have enough savings to see you through tough times.

Here’s how I diversified my savings portfolio:

  • Calculated my average monthly expense and kept 12x that amount in a separate bank account. This serves as my emergency fund as I can liquidate that whenever I need it. Even if push comes to shove, I know this can sustain me for at least one year.
  • Invest everything else in mutual funds, stocks, provident funds, gold bonds, and cryptocurrency. More on that here.

Save enough to sustain you for at least six months before you quit your job. That way, even if all your income streams dry up, you won’t have to resort to taking loans until you can build something new for yourself.

3. Do I have something to make my heart happy?

For most people, pursuing their passion means turning their hobby into a full-time job. But if you put pressure on your creativity to make money for you, it ceases to be an enjoyable process.

When you once used to create for the love of it, you now start thinking of it in terms of money and deliverables, making it hard for you to keep pushing ahead. Your work suffers, your passion dwindles, and you no longer have any ways of destressing.

“The reason I always maintained other streams of income was because I never wanted to burden my creativity with the task of providing for me in the material world.” — Liz Gilbert, Big Magic

Even though writing is my primary way of paying the bills now, it is still something I do to sate my heart. Here are some ways I plan to ensure that I continue having fun from it while also not worrying about the money:

  • I keep separate time slots in the day for “writing for myself” and “writing for money.”
  • I’m working on my novel — a work of fiction — which I know might not make me rich, but it gives me immense satisfaction.
  • On Medium, I never follow the trends that guarantee “virality.” Instead, I treat it like my online resume and only write what makes me feel fulfilled.
  • I have other hobbies that keep me happy — like going on solo walks in nature, reading, and kirigami.

4. Am I passionate enough to keep going?

No matter how much money you earn, the first few months as a self-employed person are going to be hard. You’ll find yourself looking back and comparing your current life to what could have been had you stayed in the job. So-called “well-wishers” won’t be far behind with their “I told you so”s.

To overcome all that and keep going, you have to be passionate enough to not let them bother you.

Yes, things might be hard now, but you love your craft and you believe in yourself that you will make it big, no matter what. Growth is never a straight line and the first few months will be harder than ever, but if you truly love what you’re doing, it won’t feel like a chore.

If you’re passionate enough about your goals, you’ll find ways to keep going even if the entire world seems to be working against you. You’ll stumble, you’ll fall, but you’ll pick yourself up, brush off the dust, and keep pushing on stronger than before.

Final words

I handed in my letter of resignation a few days back and am serving the notice period now. Even then, I still get nightmares wondering what will happen if none of it works out in the end.

What if people suddenly think my writing sucks and stop paying me?

And then, I have to reassure myself that no matter what everyone else thinks, I’m talented and I know it. I believe in myself and even if all else fails, I’ll still find a way to make it work.

I wrote this article to help every creative person struggling to find a way for their art to pay their bills. But more than that, I also wrote this article for myself. I wrote it so I could remind myself that no matter how much I plan, life will always go awry one way or another. All I need to do is keep pushing on and never give up.

“At the end, someone or something always gives up. It is either you give up and quit, or the obstacle gives up and makes way for your success to come through.” — Idowu Koyenikan

The question is: are you resolute enough to not give up first?

Want to be a successful freelancer but struggling to find good clients? Check out my 90-day guide to finding your first high-paying freelance client. You’ll find 5 pitching secrets, 2 email templates, and a framework to get your freelancing career started.

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