3 Details you must tackle before quitting your day job

One of my favorite entrepreneurial quotes goes something like this:

Just because you hate your job, it doesn’t make you an entrepreneur.

I love it because it keeps antsy freelancers or solopreneurs grounded in reality.

In my mind, the best time to quit your job isn’t when you start hating your work, your boss, your coworkers, and your commute.

The best time to quit is when everything is fine.

Then you know you’re not making the decision based solely on charged emotions.

As emotional, creative, energetic types, we freelancers and solopreneurs run the risk of making rash decisions that could impact us, our families, and our lives forever.

Today, I’ve got 3 important details you should tackle before throwing a match to your day job.

vsp_logoThis article is sponsored by VSP Vision. As the national leader in eye care benefits, VSP offers affordable individual vision insurance to people who don’t have employer-provided vision care. Sponsorship has not affected the value or content of this article. Learn more at VSPDirect.com.

💔 Falling out of love with your clients? Trade some of your worst clients for the best companies in the world with SolidGigs, our premium weekly freelance job list & course library. Love your business again. Learn more »

Detail #1: Have a financial cushion that matches your life situation.

A twenty-something would-be-freelancer who isn’t married, doesn’t have kids and doesn’t pay a mortgage is in a 100% different life situation than someone married with kids and a house.

For obvious reasons.

So before you make the leap and quit your job cold-turkey, take inventory of your life situation. What bills do you have to pay each month? How many other people are relying on you? Do you have a backup plan? How much money do you need just to live the same way you do now?

Sure, you can cut back on the daily cappuccino. You might even be able to get a smaller (see: less expensive) house.

But if you have family relying on you or huge amounts of debt to pay off, there are some expenses you just can’t get around.

Make sure your bases are covered before you make the decision to leave.

Some people even advise as much as one full year’s salary in savings before you do it.

Whatever makes sense on paper for you is what you should go with, but remember: “I’ll figure it out once I’m out of this awful job” is not a real solution.

Detail #2: Plan for expenses your employer covers

It’s a common fallacy when quitting your “life-sucking day job”:

If I can make the same amount of money freelancing as I do at my desk job, I’m ready to quit.

But hold on just a minute.

Have you looked at all of the expenses that your employer covers? Health insurance, vision insurance, 401k (or any kind of savings/investments), paid time off, and more.

Keep in mind, when you’re self-employed you cover all of these yourself.

While you can go easy on a savings or investment account upfront, there are certain things you don’t want to skimp on. Health insurance and vision insurance being one of them.

Need affordable, quality vision coverage? Try VSPDirect who is graciously sponsoring this article and other efforts here at Millo. VSP Direct offers Individual Vision Plans starting as low as $17 per month. They’re perfect for gig economy workers or someone who is self-employed and looking for a vision plan after leaving a group plan through work.

Download their free guide “5 Essential Resources for the Self-Employed” by clicking here.

Sponsorship has not impacted the value or content of this article.

Detail #3: Ensure you can maintain (and ideally scale) your business

It can be easy to think that, because you have plenty of business, you’re safe to quit your job.

But will that business last over time?

If you’re a freelancer, for example, do you have any clients on retainer? (here’s how to get your clients on retainer)

Do you have passive income? (or at least income that’s recurring with little effort) Need more passive income? Read this.

Have you gone through a few months (or ever better, one full year) of running your business to understand when more money comes in and when revenue is lower?

These are all considerations to make before quitting your job.

Why am I being such a downer?

I’d like to be one of those internet entrepreneurs that tells you to quit tomorrow! Give your boss the middle finger! Carpe diem! YOLO! And all that jazz.

But I’m not that kind of person.

I want you to succeed.

And it’s been my experience that the best chance you stand at succeeding is to be incredibly patient and think through every aspect of your business before quitting your day job.

If you’ve made the leap, what other considerations do you think I’ve missed here?

tweet share share pin email

Keep the conversation going...

Have a question or something to add?

Over 5,000 of us are having daily conversations over in our free Facebook group—and we'd love to see you there. Join us!

About Preston D Lee

Preston is an entrepreneur, writer, podcaster, and the founder of this blog. You can contact him via twitter at @prestondlee.


  1. Do you have the link to the passive income article?

  2. Good article and sound thinking! But the link for passive income via client retainer does not work.

  3. I would add that it’s important to consider the good, bad, and ugly lifestyle changes that come with becoming a freelancer. Working from home (often by yourself) isn’t necessarily for everyone, and can be a major adjustment. A few questions to ask yourself:

    1) Are you a self-starter? It’s INCREDIBLY easy to sleep in that extra hour every day!

    2) Do you enjoy working by yourself? Things can get lonely in a hurry if you require regular social interaction.

    3) How good are you at staying focused and avoiding distractions? Facebook, news, Netflix – ARGH!

    Its okay if your answer to any of these questions is a little shaky, as you’ll learn to make changes over time that help you stay on track. Nonetheless, if you answer with a profound “NO” to any of these, I would reconsider giving your boss the finger!

  4. Beth Sanders says

    Great article! They’re all things I’ve thought of or read before, but some of them I think only know about because I work in accounting (such as the medical/401K etc coverage). But it surprises me how many others don’t seem to have thought of them, and it’s always good to read again, for certain.

    There seem to be two missing links that I’d like to get, if possible. The one associated with the text “here’s how to get your clients on retainer if you don’t” and the one for “Need more passive income? Read this.” It might just be my browser? But there’s no hyperlink on the text.


  5. You said “If you’re a freelancer, for example, do you have any clients on retainer (here’s how to get your clients on retainer if you don’t)?” but there’s no link. Also, the same thing occurs here: “Do you have passive income (or at least income that’s recurring with little effort)? Need more passive income? Read this.” No link. FYI. Thanks.

  6. Hello Preston. As a web designer, how would you say you do your craft (pure design, front end, development, etc)? Also, do you know what your time frame was when you decided to be your own boss and when you were in the midst of being already working full time on Millo ( no other job)?

    Your articles are great and seem geared towards helping others replicate your own journey, of course in their own way. Thank you for that.

  7. This is a good article especially for new people who want to enter in blogging world and want to make some bucks, but don’t want to leave their jobs.

  8. Preston, you’re not being a downer. You’re absolutely spot on! Too many creative types that want to start their own gig have this mindset of grandeur and secretly loathe the freelancers/solopreneurs (same thing?) for making a successful transition to self-employment. From my experience I’ve always considered to have a financial buffer as one of the most important aspects of being your own boss — and I’ve played this game for many years! Cash flow will make or break you! Clients will always pay late and there will always be slow months. It’s just the way it is.

  9. Your employer also covers about half of your taxes. You might be able to “match” your income but with paying your own taxes, you end up making less.


Need more clients?

Download our free guide:
25 Top Freelance Job Sites for Real Clients with Big Budgets