Look Before You Leap: Essential Practices for Leaving Your Day Job

Leaving the day job to provide freelance services, run your own product-based business, or consult is tempting to anyone with an entrepreneurial heart. So should you make the leap? And if so, how do you do it?

If you’ve been considering going out on your own for any amount of time, you’ve probably heard many tales of leaving the day job. Sometimes, the message is to save up and wait it out to make sure you can securely start your business. Others perform best when their back’s against the wall, so they prefer to quit before they’re ready.

No matter your unique situation, these considerations can help you figure out whether you should you stay or go.


Figure out why you want to make the leap.

Running a business isn’t for everyone. There’s the stress of everything from money to skill level… plus a bunch of little stuff day in and day out like missed emails, tech glitches, and who knows what else. You will face mindset struggles like imposter syndrome and separating what you charge from what you’re worth as an entrepreneur and a person.

Take some time to consider why exactly you want to work for yourself. Make a list of everything you’re dissatisfied with in your day job. Can you improve the situation by working with your boss to shift your responsibilities or changing roles? But maybe you find that the friction between you and your boss is so difficult that you’d rather be your own boss.

If you’re going to take the leap, it’s important to make sure that the reasons are greater than your current situation.

They shouldn’t be based on stuff like sucky coworkers or boring work assignments. There must a bigger vision for what you want out of doing your own thing – like improving your industry, having more control over your time, or the opportunity to expand your income.

Become a side hustler.

It’s really hard to be both boss and employee. You will be the one to create the strategic vision and motivate yourself with it. It’s up to you to provide your own performance reviews. A lot of your work time will be taken up with some really mundane but necessary stuff.

Start by setting up an Etsy shop and working on your listings nights and weekends. Find some freelance gigs on the side that are in line with what you would want to be doing on your own. See what happens… make sure you actually like being your own boss before making a big jump!

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Work on a financial plan.

There are loads of online resources for creating a budget to quit your day job. Rule number one is to save as much as you can because independent income is a lot more uncertain than a salary. It may take longer than you think to replace your day job paycheck. So you will want a nice safety net to support your life while you build your business.

The cost of running your business will not be zero.

Sure, you can limit your overhead (the monthly cost to keep your business open) but there will definitely be costs if you want to do things right. Often, you can start out with free tools and graduate to paid ones later as you grow. My current creative business toolbox lists everything I pay for to run my business every month. Then there are all the licenses, fees, and other costs that will vary by state and industry.

As you work through forecasting your potential full time freelance income, be careful how you count your hours. You may work 40 hours (or more) in your own business, but you won’t be making cash in each of those hours. If you’re providing services, your rate will probably be tied to billable hours in some form. Many hours will be spent on administrative tasks you aren’t used to having to take care of in your day job. You’ll need sick days and vacation time. There will be slow periods when your billable hours are fewer and farther between, so you’ll be working on things like systems or course building… and those don’t pay off in the same obvious ways.

As the boss, you’re also responsible for strategic big picture work… that whole “working on your business instead of IN your business” is now all on you.

Finally, don’t forget to account for taxes! Most people seem to recommend that a U.S. entrepreneur save a third of their revenue to pay Uncle Sam. Once you take your forecasted revenue (all the money coming into your business) and subtract for overhead (cost of running your business), taxes, and any other expenses you will have (equipment, education, etc), you’ll have a more accurate picture of your potential income after quitting your day job.

Work on your exit strategy.

If you’ve made it this far and you still want to leave your day job, then you need an exit plan. Create a timeline of how you will incrementally add more and more side hustle income to build up your client base and savings account. Decide what amount of savings and side income is enough to make the leap and work away until then.

Be as great at what you do all day as you are when you’re working on your own thing.

Your exit strategy might include alternative work options. If your job could make sense part-time, see about working fewer hours so that you have more time to build your business. Perhaps your current day job situation is untenable. In that case, work on getting a part-time job that would be fun without taking up too much brain power. Having an additional source of income like a day job or a part-time gig can do wonders for funding your dream of being on your own, so be sure to appreciate it and make it work for you.

So there you have it. Now… will you make the leap?

Join the FREE 30 Day Focused Brand Challenge:

Tie up the loose ends of your brand so you can prove your value and attract more customers. Sign up and get started today!