• Caroline Jennings

From Side Hustle to Full-Time

Overcoming the Mental Blocks Standing in Your Way



"What's stopping you?" It was a question I couldn't get out of my head when I began to seriously contemplate quitting my day job and going full-time with Word of Web.


I remember the moment it hit me. Fear was the only thing standing in my way. I had already developed a solid client base, accumulated sufficient startup funds, and completed the basic new business owner to-do list – registering the LLC, opening a business bank account, writing a business plan, and so on. On paper, I was totally ready to go.


As much as I hated to admit it to myself, I was the only thing stopping me. I feared failing. I feared "not doing it right." I feared leaving the comfort and security of a salaried job. It was these fears that were keeping me from pursuing what I knew in my gut to be my calling.


People often ask "what's stopping you?" with a rhetorical bend, or in a way that implies you should just "go for it," throwing all caution (and potentially valid hesitations) to the wind.


But for any of you out there considering making the leap from side hustle to full-time, I encourage you to really sit with the question – what's stopping you? Is it money? Skill? Time? Or is it just some artificial barrier you've constructed in your mind?


But for any of you out there considering making the leap from side hustle to full-time, I encourage you to really sit with the question – what's stopping you?

I've had the pleasure of working with a multitude of aspiring entrepreneurs and freelancers throughout my journey with Word of Web, and I hear many of them struggle with these kinds of mental blocks. They have done all of the preparing, perfecting, and planning humanly possible, but they still don't feel ready to pull the trigger and go full-time with their business.


Sure, some of their reasons are perfectly valid – I can't afford the risk right now, I'm waiting until I hit $X in monthly revenue, I need to build my client base, etc. And sometimes, the timing just isn't right (can you say global pandemic?).


But oftentimes, I've observed that the main thing holding people back is nothing more than a mental block that has become so deeply entrenched that it goes unnoticed. And that's why it's the most formidable opponent of all.


For me, the inner enemy was fear. For you, maybe it's self-doubt, imposter syndrome, perfectionism, anxiety, or a rigid set of rules and expectations you (or your parents/friends/colleagues/partners) have imposed on yourself.


It doesn't really matter what particular form your monster assumes. What does matter is calling him out – looking at him square in the face and saying "I see you, and I'm not going to let you get the best of me."


I'll leave you with a quote (paraphrased from Stanford professor Irv Grousbeck) I heard recently: "Regret for what you have done can be tempered by time. Regret for what you have not done is inconsolable." For any of you freelancers or entrepreneurs out there struggling to make the big move to full-time, I can't imagine a more compelling call to action.


"Regret for what you have done can be tempered by time. Regret for what you have not done is inconsolable."

You're never going to feel 100% confident that it's the "right time" to take your business to the next level. But once you've done it, I'm betting you'll feel 100% certain it was the right decision.



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