When it’s Time to Begin Freelancing: 9 Key Signs
When is it time to begin freelancing? What are the signs to quite your 9-5? Here’s the truth: When you are not making enough income, dissatisfied with the requirements of the job, confined to a specific location, unfulfilled in your daily routine, or simply want something new for your life, then it's time to begin freelancing.
The seven key signs will show you that it's time to begin freelancing on the side.
1. You aren’t making enough income
Here’s the truth, you want to be satisfied with the income you’re making, but simply put, it’s not enough. Inflation is killing the 9-5 worker. It did me.
I was making a decent salary, $50k+/yr — great for anyone overall. But here’s the problem: It wasn’t supporting my family.
So I decided to start freelancing for some side income. I chose content marketing in social media
2. You’re confined to one location without flexibility to Leave and crave control over your schedule
Most salary, W-2 workers are required to work ina specific spot at a certain time duration. In return, you get a tax break on income and benefits. The problem is that someone else controls your time and location — not you.
This didn’t sit well with me. I wanted control of when I wanted to see my family and when I wanted to work. I felt as though I was honorable to get the things done I needed to, I simply want to do it on my own timeframe.
3. You’re dissatisfied with the requirements of the job
Maybe the day-to-day grind is just that, a grind. And you’re tired of all the requirements.
Or maybe you’re killing it in the role and you’re board with the checklists and systems. You crave something new.
Freelancing opens up new rhythms. And you’re in control of it.
4. You’re passionate about building
If the thought of building something from the ground up excites you, then freelancing is for you. It invigorated me to know that I could go out, make connections, offer a solution to their problem, and make money. I was the one in charge of my business and it’s growth, not my supervisor.
5. You Want to Begin Working on Passion Projects
For some, they want to create something new without being put into a box. Let your creativity flow. Freelancing allows you to decide what you want to work on. (Note: Watch out for “shiny object syndrome.”)
6. You’re unfulfilled in your daily routine
Drive to work. Work. Eat lunch. Work more. Workout. Drive home. Watch Netflix. Scroll. Sleep. Repeat.
Sound like you?
Maybe it’s time to disrupt the schedule with something new.
A freelance gig can brighten the day with new opportunities to create and produce.
7. Your skills are in high demand within your industry
According to Upwork, these and more are the highest paying freelance jobs for 2025:
Maybe you
Media buyer
Public relations manager
Business consultant
Cybersecurity developer
Financial consultant
AI professional
Blockchain developer
Videographer
Data analyst
Photographer
If you’re in one of these jobs as a W-2 employee, you may want to consider freelancing.
8. You have a strong professional network or portfolio
You’re a networkling butterfly at events, making connections and building relationships. Netowrking is key for building sales when starting freelancing.
Further, you may have awesome case studies that shows stellar results. This builds clout for starting out as a freelancer.
9. You’re passionate about your work and ready to invest in yourself
“You will be the same person in five years as you are today except for the people you meet and the books you read.”
Learning is the key to success. Start by reading books relating to your life and business issues. Self investment will always return back to you.
Your current job no longer aligns with your goals or values
This is a hard one to pinpoint, it’s a harder one to swallow. It can be disheartening to consider that it may be time to part ways with your main job because you no longer align with it.
Maybe you’ve grown over the last few months or years and your company culture hasn’t. Or the company is stagnant in their mission and only care about the bottom line. Either way, it’s good to evaluate your goals from time to time to ensure it’s near the company’s you work for.