Freelance Life

5 Signs It’s Time to Quit Your Day Job

It is no easy feat running two enterprises at once, be it a job and a side-hustle, or a small business and a family, or school and work.

Yes, we live in the age of the multi-tasker, where gadgets and apps make such endeavors easier, but easier is not the same as easy. Indeed, taking an idea, executing it, making a profit, and then keeping it going takes a lot of mental, emotional, physical, and financial bandwidth. It demands total commitment.

If you can’t give your side-hustle the attention it deserves, because of family, another job or whatever, while it may not be fatal (it is a side hustle after all), but it is probably not ideal either. The nature of a small business or whatever sort is that the sooner you can give it 100% attention, the better, because that is how you stand the best chance of success.

But this caveat is also important: The timing has to be right. If you started a business with the coffers flush, bully for you, pass Go and get $200. But everyone else – the part-timer, the weekend warrior, the bootstrap entrepreneur, the side-hustler – finds themselves asking the same question you are asking: When I can I make this my full-time gig?

Good question.

Are there signposts that say the time is right? You bet. Here are the Top 5 Signs That You Can Quit Your Day Job:

5. You are headed in the right direction:

Starting a business at home, at night or on weekends requires not only that you keep up with your regular job, and your home or family commitments, but also that you dedicate most the remaining time to the business. Tough to do, that.

As such, it will take a while to get off the ground, gain altitude, and fly in the right direction. But once you get past that startup phase, once you have a tailwind and are headed in the right direction, you know you are on the verge of being able to let go of the safety net that is your day job.

4. You know what you are doing:

A corollary to No. 5 is that you are past the novice stage and actually know what the heck you are doing.

Sure, you can fly earlier, but if you don’t really know what works and what does not, you will more likely fall than soar with the eagles. (OK, no more; I think I have beat that metaphor to death!)

3. You have reliable customers:

Notice I did not just say that you have customers, but that you have reliable customers. They are not the same thing. Customers come and go.

Reliable customers are different. They found you and like you and like working with you or shopping with you. Reliable customers give you both the confidence and the financial wherewithal to do without the safety of the regular paycheck, benefits, and healthcare.

2. You make enough money to (almost) live on:

Again, notice “almost.” If your side-hustle gives you enough income that you believe you can do even better if you go full time, you are probably right.

But this should also mean that you have saved some money. Quitting will hit your wallet, as will ramping up, as will buying your own health insurance and more. Until you quit, the money you make in your extra endeavor should also provide a nest egg for the full-time version.

And the No. 1 sign you are ready to quit your day job . . .

1. You can’t not do it:

When you get to the point that the business is going so well, when opportunities are presenting themselves, when it’s so fun and profitable that you miss it and think about it when you are not doing it, when not doing it more costs you money, then you are ready to do fly like the wind, my friend. (Sorry, I couldn’t help myself.)

And when that time comes, the only left to say is . . . bravo and good luck!


Steve Strauss

Steve Strauss is the senior small business columnist at USA TODAY, the Editor-in-Chief here at Small Business Connection, a speaker and spokesperson. He can be reached at

More Articles You May Like

Back to top button
Share this
Send this to a friend