Is Freelancing Right for You? Here’s How to Decide

We aren’t all built for the 9-to-5 lifestyle.

The mind-numbing spreadsheets. The hot-headed bosses are eager to unleash. (Not to mention those insulting lateral “promotions” that undercut confidence.) You want out — and now!

You’re not alone!

Americans are ditching the workforce by the millions to join the freelance world. With 64.8 million Americans representing the gig economy in 2020 alone.

Should you hand in your resignation letter and become a freelance writer starting today? Or is it better to wait for the pink slip to travel down the pipeline? 

Neither. If you’re wondering whether freelancing is right for you, with your future on the line, this is not a decision to make lightly. 

Here’s how to decide:

How Is Your Current Financial Situation?

Even if you’re a ten-year industry veteran with a Master’s Degree and Fortune 500 references on speed-dial, the gig economy requires time to make headway. 

Clients can be stingy with newcomers, and perfecting your rates to be more profitable can take some time.

Until you find clients offering steady work, you might be in the red for a few months. That $1,500 tax refund that makes tax season worth the effort will be gone, too, since you’re now self-employed. And health insurance falls back on your shoulders.

Make sure you have decent savings account to fall back on as you get your feet wet and break into freelancing for good.

Is the Classic 9-to-5 Lifestyle Getting Old?

Some of us experience mid-afternoon jolts while others suffer exhausting slumps. Some struggle to function until 10 a.m. even post-coffee while others take the term “night owl” to new extremes.

Unless a client requires you to “clock in” daily at a specific time, your freelance schedule falls to your own discretion.

That means you can take breaks when, where, and however long you want, work weekends, or work an odd 11 p.m. to 4 a.m. shift when insomnia hits hard. 

Of course, the downside is that you may never really be off the clock and find yourself working well beyond that 40-hour week.

Are You a Self-Starter?

Do you struggle with finding your mojo while on the clock? 

Then jumping ship and joining the freelance world can feel like an unexpected slap to the face.

There’s no steady eight-hour shift. Lunch breaks can drag into the three-hour territory. Not to mention, your next approaching deadline can be weeks away.

A skilled freelancer must be a disciplined self-starter that doesn’t need a boss breathing down their neck 24/7.

If you’re not chasing down proposals or submitting projects on-time, your rent goes unpaid. It’s as simple — and complicated — as that!

Do You Have Industry Expertise?

The freelance world can include any non-salaried position. Some gigs are more tedious or convenience-related than anything, like mowing lawns or delivering food. 

But others require in-depth expertise to keep you in the running for an open gig. 

Before you dive into freelancing head first, consider your qualifications:

  • A degree (related or not)
  • Related field experience
  • Volunteer experience
  • Relevant hobbies or skills
  • Industry references

About half of us will change career paths at some point in our lives, and the sudden beeline toward freelancing might be your big switch. 

This doesn’t automatically disqualify you for a novice gig. But it does help to build your skills and learn about the industry via workshops, online certifications, and DIYing projects.

Can You Function Outside of the Cubicle?

Are you among the 7% of workers who absolutely love the classic cubicle set-up and their own private workspace? 

Do you hang family photos by your desk, fiddle with kinetic sand tubs, and enjoy organizing documents in your very own filing cabinet?

It’s quiet, easy to focus in, and even somewhat homey.

But unless you set-up a home office free from distractions, working the freelance life is a totally different beast. It’s challenging to ignore the TV chatter, slash those constant kitchen snack trips, and resist your pet begging for snuggles.

Can You Survive With Limited Social Interaction?

Joining the freelance community comes with some lovely newfound freedoms — financial, schedule-wise, and even behavioural (wear pyjamas if you want!). But surveys show that some 39% of freelancers battle loneliness and social isolation.

Receiving a business call from a client or chit-chatting with a customer via email could very well be the social highlight of your day. 

If striking up conversations in a colleague’s cubicle made that midday slump more bearable, freelancing may be too lonely.

If you can sacrifice the office chats, don’t forget to nourish your social life elsewhere. Call friends, go downtown, or even visit the grocery store from time to time.

How Are Your Business Skills?

Freelancers wear several hats that go well beyond industry skills and knowledge. When you fill those massive freelance shoes, you also double as your own agent. 

Added to your already-full plate are business skills and HR woes like:

  • Rate negotiations
  • Setting, extending, and negotiating deadlines
  • Offering industry-related feedback
  • Networking
  • Tracking self-employed income & business spending


There’s no union or HR crew on-call and ready to jump to your defense if a client relationship goes awry. Learning when to say “no” and fighting for rightful wages are necessary freelance skills that take time to build.

Do You Crave Control Over Your Future?

The “odd job” freelance stigma (ex: lawn mowing or driving for Uber) couldn’t be further from the truth. In fact, the latest figures suggest that skilled freelancers earn higher wages than 70% of regular workers — averaging about $28/hour.

While consistent freelance work is hard to come by during those first few months, the earning potential is near-unlimited.

A standard 40-hour workweek at $25/hour will always yield a $1,000 weekly paycheck (minus taxes), no matter how much work you squeeze into it. As a freelancer, you can charge per project and maximize your earning potential.

Don’t wait for that measly $100 Christmas bonus, or pray for a much-needed raise. Take control of your finances by hopping on the freelance bandwagon.

How Often Do You Want to Interview?

The office job monotony gets real old, real fast. 

But at least you have a predictable bi-weekly paycheck without having to continually interview to ensure the rent gets paid.

The gig economy is often competitive and comes with two stability concerns:

  1. Other applicants proposing low-ball offers, leaving you jobless or forcing you to lower your rates to snag a project
  2. Hopping from client to client since many only offer short-term opportunities

Unless a client offers “steady work,” you’ll be on the job scramble monthly, weekly, or even daily. It can be tiresome to craft custom-tailored proposals so often with no guarantee you’ll fill your schedule next week.


The freelance world isn’t for everyone. 

And, it could take months before you’re on a regular work schedule that both jives with your social life and covers the financial end of things.

But maybe you’re still on the fence. 

What if you hate it and are now left jobless?

If you want to test the freelance water before quitting your day job, there’s no harm in splitting your time between the two. Create a profile on Upwork or Freelancer.com, pick up a gig or two each week, and see how you like it.

Maybe freelancing only looks tempting because it can’t possibly be worse than your current position. If that’s the case, apply to a new company!

[Author bio]

Adam Marshall is a freelance writer who specializes in all things apartment organization, real estate, and college advice. He currently works with Arch at Bloomington to help them with their online marketing.

Pranesh Balaji
Pranesh Balaji Is a Blogger and an SEO professional. Co-founder of Bigmixseo, I have 2 years of experience in SEO & 1 year of Successful blogging @ pantheonuk.org. I have a passion for SEO & Blogging, Affiliate marketing, & to invest in high trading stocks. " Sucess is the ability to go from one failure to another with no loss of Enthusiasm "