Save at least six months’ worth of money.
Start the business on the side.
Have a fool-proof plan.

There are many creatives and entrepreneurs who, on stages or the internet, tell us how to properly prepare to quit our jobs. Saddled with hindsight, these individuals’ advice espouses the “shoulds” of a leap well-planned and not the “dids” of how their own journey panned out.

One year ago, I left corporate America to pursue my path towards freedom and creative bliss. My experience taught me that while there is sound advice floating around the internet — there are many things I could’ve only learned mid-air and not in the preparation to jump.

Here are six surprising things I learned about taking a leap of faith and quitting my job.

You will never save enough money

“The three most harmful addictions are heroin, carbohydrates, and a monthly salary.” — Nassim Taleb

Three months after leaving my job, I stumbled upon a program that would give me the exact skills and tools I’d need for a project I was working on. Only thing was, it cost $1,500. Immediately, a wave of fear and anger swept across my body as I stared at the price tag. Why hadn’t I married rich? Why was I not ballsy enough to get a sugar daddy? Why hadn’t I tried to just do this career pivot on the side?

You won’t read an article on quitting your job that doesn’t speak about saving as much money as possible. And truth be told, there is complete merit to what the finance experts tell us. However, it’s also worth noting that even if you save a year’s worth of money, it’ll never feel like enough.

The fact is, if you were making money for at least five years, going without weekly or bi-monthly paychecks can be nothing short of anxiety-inducing.

So yes, be smart about your savings but also understand that leaping requires that you confront financial discomfort. Start to get comfortable with the idea that quitting may bring up some of your old stories and beliefs around money. Prepare for this by setting aside time for financial planning and by working on the spiritual beliefs you build around the energetic flow of money.

It’s okay to stay

Our culture celebrates big, bold moves. The bolder, the better. From this, we’ve come to applaud and glamorize entrepreneurship, putting it and its constituents in an elite league of their own.

Oddly enough, I couldn’t have felt less glamorous when news of the coronavirus started to slow down client work in April; or when I had to still force out creative work during the height of BLM protests in June; or the myriad of moments where I yearned for a consistent check.

Most of us wading entrepreneurial waters know that we don’t do it because of the cool factor. Being cool is not enough to wake us up in the morning or keep us going after the applause die down.

But no matter what side of the grass you’re on — staying in a job or taking a leap of faith and leaving — there will be manure. It’s a matter of choosing your preferred fertilizer.

That’s why you have to figure out if whatever is on the other side of quitting is something you really want. Maybe it’s not entrepreneurship for you but instead time home with your kids, switching industries, or taking a pay cut to do more work you love. Whatever it is, you have to weigh if the disadvantages of this new route are something you’re not only okay dealing with — but also would prefer to have compared to where you are today.

And if you decide it’s not, know that’s worth celebrating too.

Know your ‘why’

I tried to talk myself out of taking the leap multiple times. There were various moments in which my job — a rather sexy one from the outside — didn’t look so bad. So, determined to not imprudently leave this sexy job, I tried to carve out time on the weekend to pour into the career of my dreams. However, trying to figure out this new path — while still on my current one — was not satisfying enough. And that’s because my why was tied to freedom and creative exploration.

Figuring out your why for leaving your job helps you evaluate the micro-decisions tied to doing it.

I find it interesting how many people’s why behind quitting is because they don’t like their boss or feel like they need a break from work. All the while they minimize the challenges of what awaits them on the other side of leaving.

Knowing your why will ensure you don’t leave a good job if all you truly need is to switch teams or take an extended vacation.

Let regret lead you

As I considered leaving, I had a memorable conversation with a close confidant.

“You can stay and be good or you can leave and be great,” he told me.

Knowing how “sexy” my job was, he knew I’d be fine if I stayed. But he also knew me enough to know that I could never fall in love with “good” until I at least attempted “great.”

I’ve found that it is not usually complete dissatisfaction or hate that causes a person to contemplate leaving their job. Instead, it is a weird middle ground feeling; a pervasive thought that something just isn’t right. You may look at the people around you — your manager, others in various departments, or those across the industry — and cringe at the thought of having any of their jobs.

If you flash forward to what your life would be like if you stayed a few more years and received a couple of promotions — how do you feel? Do you get slightly nauseous at the vision of your future life? Do you think, “this future life doesn’t feel like it belongs to me”?

If so, you have all the answers you need to make a pivot in your career. At this point, it’s not a matter of if you need to leap — but when and toward what.

You don’t need all of the answers

What’s your timeline?
What exactly will you do for money?
Do you have, like, a plan?

The moment I started to tell close family and friends about my decision to quit my job, the questions rolled in — and never stopped. None of the queries thrown my way were things I hadn’t wrestled with at night. But seeing your monsters in the morning casts them in a totally new light.

So, at times, the questions were overwhelming. But answering them out loud allowed me to see the flaws and gaps in my thinking. And it also eventually taught me — it’s okay that I don’t have all the answers.

This exposes two key points I’ve found in leaping: 1) be careful of who you share your plans with when they’re in the seed stage and 2) remember the adage, “you don’t have to see the whole staircase to take the first step.”

Your support system wants the best for you but there comes a point where you have to trust you know your intuition’s call better than they do. And while planning your exit strategy is important; understand that inspired action is often the best way to receive more answers, clarity, and direction.

A ‘leap of faith’ for a reason

“And, when you want something, all the universe conspires in helping you to achieve it.”
― Paulo Coelho, The Alchemist

When I decided to quit my job, I tried to attack that challenge like I would any marketing plan. I broke down each workstream I wanted to build and creative project I wished to start. I included deadlines and finessed my budget. I had conversations with trusted friends and made my lists of pros and cons. But when I reached my planned date to bid corporate America adieu — I couldn’t go through with it.

That’s because I was in a season of constant movement, causing me to neglect self-care and my spirituality. I had disconnected from my why and, more importantly, from my sources of strength.

And so, I got back to it. I started meditating each morning. I listened to Christian sermons, Monk leaders, and the best self-help gurus on YouTube. I reinstated my hot yoga membership and ran outside once a week. I put good things in my body and said no to social invitations, opting to prioritize the things that I knew would be good for my soul.

And with that, I found my way back to myself; to my inner source of courage.

What pushes most of us from an idea to implementation is more about our mindset and belief system than it is about our plans and processes. We don’t need to agree on what we call a higher power; simply finding ways to make time to feed your spirit is what you need to gain clarity and courage. And doing so is also how you properly rest and reset before a big leap.

There is endless advice about what to do as you plan to take a leap of faith and quit your job. And yet, if our advice fails to underscore that much of the revealing happens in the jump — we are missing the point completely.

Taking that leap been the greatest gift I could give myself. It’s shown me that I can, indeed, create a life in which I have control over my schedule. It’s allowed me to work with great clients across tech, wellness, and finance. It’s gifted me an amazing yoga teacher training experience 3000 miles from home.

It’s allowed me — via an unlikely global pandemic — to spend quality time with two of my favorite people: my parents. It’s given me time to take part in writing and storytelling programs, including the first cohort of On Deck Writers. It’s offered me the headspace to go from never having published my work to publishing nearly 30 articles.

And, more than anything, it’s given me faith in myself and the Universe to work on my behalf.