The Romance and Tragedy of Freelance

Suggestions From a Newbie to a Wannabe

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.
The Freelancer Life (Source: Condenast/New Yorker)

Most of the working professionals I have met, at some point in their lives, very vividly dreamt of shutting down their laptops dramatically, putting on their game face, walking up to their managers and announcing that they are quitting their jobs. For they are now taking the plunge into the sweet sweet world of freelance where unicorns replace wicked bosses and rainbows replace drudged cubicles.

“Thank you so much, it’s been a great learning experience, personally and professionally.” Mic Drop.

I am happy to announce that a few months back, I realized this dream. And I really want to say that I worked happily ever after, but that wouldn’t be true, not entirely at least. Don’t get me wrong, its been a fulfilling time so far, but nowhere close to being as dreamy as I thought it would be. So here I am, in the interest of my unknown LinkedIn gang, sharing a list of prositives and consitives (Yes, these are the full forms, they have to be!) for those kindred spirits who have no idea what they are getting into.

What might work-

  • World’s your oyster aka Flexibility: And don’t we love it? In our bodies and in our schedules. The freedom to work, whenever you want and wherever you want, is easily the biggest prositive (I’m sticking to it) of being a consultant or freelancer. As long as you have interwebs between your fingers, your workstation could be a sea-side shack or a cabin in the woods. Nothing will stand in the way of you delivering to your clients while experiencing the joys of different views every few days or weeks.
  • You do you aka Ownership: This is a big one, for those who detest the bureaucracy of an established workplace where most briefs are expected to be executed without room for discussion or dissent. Being your own boss is exhilarating most times, and scary some times. Either way, you will learn a great deal from knowing that 100% of what you deliver is coming from you. No stolen ideas or forced-down strategies in this wonderful world, ladies and gents.
  • Keeping it fresh aka Improvisation: Stemming from the same school of ownership, freelancing lets you improvise your vision if you aren’t too invested financially (in which case, sorry sweetie!). The proverbial sky is the limit to what you can do, as long as it flames your passion. A move from writer to filmmaker or marketer to strategist, nothing is impossible with determination and enough bucks in the bank.

What usually doesn’t-

  • People or lack thereof: As a perennial people hater, I was surprised to discover how much I miss a social environment to work. You could be the most introverted of the lot, but I promise you will miss going to a building full of human beings you are familiar with. Even the pesky HR manager you swore you hated with all your guts. And coffee shops may provide occasional respite, but unless you are big on conversations with strangers (which this author isn’t), get used to some amount of isolation.
  • Self discipline or lack thereof: This is easily my biggest challenge. Bossing yourself doesn’t come naturally to most people. I mean there is the new season of ‘Stanger Things’ waiting to be witnessed and one more episode never killed anyone. Well, except it did- your drive and discipline (and the money you could be making!). Getting out of the black hole of social media and on-demand entertainment, to focus on work or business development, is a massive mountain to climb. Take it from someone, who has devoured most well (and not-so-well) rated shows on all available streaming services available in the last few months. Damn you talented content creators!
  • Sureties or lack thereof: Like most things in life, freelancing comes with limited guarantees. In some sense, this is what makes the journey exciting, but for those who need a steady flow of income, it can be daunting. The consistency of work is not guaranteed and nor a complete return on time investment. You would do well do safeguard your work by ensuring legalities are taken care before you start work or pray hard that the humanity hasn’t gone to the dogs yet. If I were you, I would choose the former.

Before wrapping up this admittedly obvious list, I do want to mention another challenge that I am striving to overcome. Without trying to sound mighty philosophical, I would advise the future freelancers to also consider the repercussions of a possible identity loss that comes with quitting a job. Our society works extra-hard to ensure we make our titles our identities, and so far its doing a magnificent job of it. Therefore, apart from the financial risk, you do run the risk of impacting your mental health.

But like all things nice, pretty and revolutionary, successful freelancing is a game of initiative and perseverance. You don’t get to sip your Pina Colada on the beach on a weekday without sacrificing your Sundays to ‘urgent’ client needs. Notable freelancers and eventual entrepreneurs do say its addictive too. I’m on the fence here, but as the famous anonymous once said- At the end of comfort zones, lie unicorns and rainbows.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...


Catch Fire To Transform Your Life

by Jesse Gernigin

John Seymour of ‘Sweet Chick’: “A vehicle for negativity to transform into positively”

by Karina Michel Feld

50 Things I Wish I Knew As A Beginning Freelance Writer

by James Murphy

Sign up for the Thrive Global newsletter

Will be used in accordance with our privacy policy.

Thrive Global
People look for retreats for themselves, in the country, by the coast, or in the hills . . . There is nowhere that a person can find a more peaceful and trouble-free retreat than in his own mind. . . . So constantly give yourself this retreat, and renew yourself.


We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.