How to Prepare to Leave the 9-to-5 Behind

John Schneider

Less than a year ago, I quit my job.

I didn’t quit working. I just quit working for someone else. I feel as good today about that decision as the day I left.

The best part about quitting my traditional job was watching the cycle of emotions my friends and family went through after I told them I quit.

Their eyes opened wide when they heard the news. This was followed restrained winces, as they considered the loss of steady income, health, and insurance, security, two weeks of vacation a year. All those things we expect from a job.

Then, as if on cue, they’d drift into a daydream and pondered quitting their own jobs.

If you dream of a life of employer independence, you too can leave the 9-to-5. Here are five keys that helped me take that major step:

Sticking to what I know.

One of the main reasons people say they can’t quit their day job and start their own business is that they don’t know what to do. Don’t think too hard about it and get stuck in analysis paralysis. Stick with what you enjoy, are already doing, or are good at doing.

Listen. If the universe is pulling you in a certain direction, go.

My and my husband’s careers have been in finance. Despite this, when got together we had a combined total of $51,000 in credit card debt. We applied our theoretical and practical knowledge to pay off our debt and turn our net worth around.

We enjoy finance, investing, and financial planning. Because of our experiences and our desire to help others with their money, we’re using our personal and professional experiences as the foundation of our business.

We put ourselves out as writers, speakers, podcasters, and experts on personal finance and we’re now helping others and, in turn, growing a business that let me leave the 9-to-5 grind. David’s not far behind me.

We saved money.

Before I quit my W-2 job, we added an additional $10,000 to our existing emergency savings account.

We did this by cutting back on non-essential spending and putting it into our emergency savings account with no bells or whistles. We don’t have debit cards or checking writing on this account. We don’t connect it to other accounts for outgoing electronic funds transfers (EFT). This money is hard, though not impossible, to access. This reduces urges to spend this money on whims.

We’ve resumed some of the habits we used to pay off our $51,000 in credit card debt. This includes only buying groceries that are either on sale or for which we have coupons. We cook at home rather than dine out. Cardboardeaux has replaced Bordeaux because it’s cheaper per bottle and stores longer.

All of this is temporary and we know this is temporary. We can live frugally today to grow our business because we lived frugally yesterday to pay off our debt.

Hustling harder than ever.

Thomas Edison said, “Opportunity is missed by most people because it is dressed in overalls and looks like work.”

I used to think I worked hard at my W-2, but I worked just hard enough to keep my boss happy.

I’ve never worked so hard in my life as I am now on our business.

With each day, the 9-to-5 is getting smaller and smaller in the rearview mirror, but to say it’s been easy would be disingenuous.

There’s a meme of an iceberg I frequently share on Facebook. Ten percent of the iceberg is above water and represents the “overnight success” that people see. Ninety percent of the iceberg is below water and represents the work no one sees: waking up at 4:30 am, working until midnight, on weekends, and holidays.

There are times that I’ve questioned if this is worth it. When I hear about rush-hour traffic jams, friends stressed about their bosses and disappointment with nominal raises, I’m reminded that it is.

I prepped.

There were steps I took before I decided to actually leave the 9-to-5.

I researched and updated my health insurance, acquired life insurance, and created a plan to consolidate my employer-sponsored 401(k) with my personal broker.

We talked with our accountant about what my W-2 and 1099 employment status changes would mean for our personal income taxes. We created a week-to-week budget that accommodates our drop in regular income.

Being thorough and meticulous before I quit has made temporarily cutting our income in half a little easier.

I took the leap.

Finally, I took the leap. Many people struggle to make big and seemingly scary life changes because they’re waiting for the perfect time. There will never be a perfect time. As Voltaire said, “better is the enemy of the good.”

Many people struggle to make big and seemingly scary life changes because they’re waiting for the perfect time. There will never be a perfect time. As Voltaire said, “better is the enemy of the good.”

To be fair, I delayed my original termination date by 90 days because my employer asked me to complete a project on which my team was working. I considered delaying my termination again because the economy showed signs of weakness. The problem is we can always come up with reasons to stick with the safe and familiar.

Some people might say we should’ve saved more than that extra $10,000. Others might say I should’ve waited until after the last presidential election ended. Still more might say leaving, at all, was foolish.

Despite all the reasons I could’ve manufactured, I leaped and I don’t regret it.

If your dream is to leave the 9-to-5 behind, too, these five steps may help you. I challenge you to be thorough and meticulous before you take such a leap, but I also challenge you to not get paralyzed by fear or analysis.

As Zig Ziglar said, “If you can dream it, you can achieve it.”