3 Vital Lessons If You Plan to Quit 9-5 for Freelance Writing

This is perhaps all you need to know

Ajayi Olalekan
Ditch the Grind
3 min readApr 4, 2024

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Photo by Sam Sabourin on Unsplash

Going from the security of a 9-5 job to the freelance writing world can be both thrilling and daunting.

How do I know? I resigned from my 9–5 on December 19, 2019, and I’ve worked as a full-time writer since.

While the idea of being your own boss and pursuing your passion is exciting, the transition comes with its own set of challenges.

Whether you’re just starting to consider this career move or have recently done so, these three vital lessons will prepare you for the road ahead.

1. Have a plan

The first and arguably most crucial step is to have a solid plan in place.

Transitioning from a stable income to the unpredictable nature of freelancing can be financially jarring if you’re not prepared.

That is why saving up a financial cushion before you quit your day job is essential.

Experts recommend having at least 6-12 months' worth of living expenses saved up to give you a runway as you build your client base and steady income stream. This safety net will alleviate some of the stress and pressure that comes with the territory.

Beyond the finances, map out a clear action plan for finding clients, marketing your services, and establishing yourself in the industry.

Jumping in without a strategy can lead to wasted time and frustration. And if the idea of a plan sounds too complex, the second point will uncomplicate it for you.

2. Get mentorship

No matter how much research and preparation you do, there will be aspects of this new life that take you by surprise. That’s why it’s invaluable to have a mentor – someone who has successfully walked the path you’re venturing down.

A mentor or a coach can provide guidance, share inside knowledge, offer accountability, and help you navigate the inevitable bumps in the road. They can shed light on potential pitfalls to avoid and shortcuts to save you time and energy.

Reach out to experienced freelance writers you admire and respect. You’ll be surprised how many are willing to pay it forward and share their wisdom if you come from a place of humility and gratitude. And you could also enlist their coaching services for a fee. That said, I have an offer for you at the end of this piece.

3. Be patient with yourself

Lastly, you must be patient and give yourself grace throughout this transition period.

Building a sustainable freelance writing career is a marathon, not a sprint. There will be ups and downs, wins and losses, delays and detours along the way.

When you’re just starting, it can take considerable time to find your groove, land your first few clients, and generate a steady stream of income. There may be periods of uncertainty where you question your decision. There could even be times you would want to go back to your soul-sapping 9–5 job.

Understand that this rocky terrain is all part of the journey. Embrace a long-term mindset, learn from your mistakes, celebrate small wins, and don't be discouraged by the bumps.

Stay focused and persistent, continually improving your skills and processes.

Wrapping Up

The rewards of successful freelance writing – creative freedom, flexibility, and unlimited income potential – are well worth the initial hurdles. Approach this transition with a plan, guidance from experienced voices, and a healthy dose of patience. You’ve got this!

Need help with transitioning and how to build a profitable writing business and the lifestyle of your choice? We could work together. But firstly, click this link and let’s hop on a free 15-minute clarity call.

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Ajayi Olalekan
Ditch the Grind

Premium Ghostwriter 🇳🇬 🇺🇸 🌎 Get my free ebook (Passion to Profit) - https://shorturl.at/DHNT4 | Get my Medium Masterclass — https://selar.co/1d97cl