Ask JKE: “How Did You Prepare to Jump?”

Words by Jackie Kai Ellis

Photo by Tomas Anunziata.

Ask JKE is our monthly advice column written by Jackie Kai Ellis. Submit your questions anonymously here.

Dear JKE,

When did you know you wanted to work for yourself? How did you decide? When did you know you were ready? How did you prepare to jump?



Dear KHJ,

I’ve wanted my own business for as long as I can remember. Both my parents owned their businesses and, when I was a child, conversations at the dinner table revolved around solving the puzzles of their clients, employees, and contracts. I tagged along with my mom as she went from meeting to meeting, and rolled bags of pennies (aka the “babysitter”) in empty boardrooms at my dad’s office. This life was familiar to me.

Entrepreneurship for them was as challenging, risky, and grueling—as it is for entrepreneurs today—but necessity decided their path. As Chinese immigrants with little education, holding down multiple jobs as janitor, waitress, cashier, or construction worker weren’t enough to get by, let alone enough to care for our extended family. The need to start businesses far outweighed fear; and so they jumped, but carefully.

My parents wanted a more secure career for me, a steady paycheck. Above all, they didn’t want me to struggle for money, because they did so on my behalf for so long. But the dinner table puzzles, the industrious “Swiss army” nature of entrepreneurship, the twists and turns—it all ended up fascinating me much more (and suiting me much more) than the “traditional” careers they had worked so hard for me to have.

For me, the realities of entrepreneurial life were demystified early on. I saw firsthand that business owners rarely clock out. I saw that they didn’t have just one boss, but were responsible for each and every client. They worried about employees, weighed risks, and navigated social politics. But I also saw that they had the freedom to craft how they worked, to shape the values they worked for, and to choose which risks were worth taking.

I have even greater freedoms and wider choices. I can afford to take risks because I have less at stake; a family of 10 is not depending on me for their survival. This isn’t to say that I don’t get scared. I have my fears. They are different from survival, but no less paralyzing if left unexamined. I fear failure, and I fear my ego being bruised, my self-worth still somewhat coiled together with the world’s definition of success. Everyone fears something: it’s what holds us back.

Look under the bed

Fears are natural and wonderful things. They protect us from danger. They also make us human, humble, and capable of empathy. If we don’t look under the bed, though, we won’t really know what monster we have on our hands, or if there is a monster at all. The longer we avoid it, the more the monster can grow to irrational proportions. So, the way to deactivate fear is by simply looking at it.

The monster out there

I frequently have business ideas that seem fun or lucrative. Though I often deliberate each and even write business plans for each, at the end of my process, I choose not to pursue most of them.

For me, the purpose of the business plan is to ask questions. It’s to clarify the vision, to understand my intentions, to know the risks, the investment, the sacrifices, the benefits, the viability of the idea. Ultimately, it’s to see if I truly feel passionate about the idea—enough to do the hard work to make it successful. It’s to test how much I want it.

The monster in here

When it comes to starting businesses, most of us are scared of losing security, of failure, or of embarrassment. Sometimes we are afraid that failure will confirm an even greater fear: that maybe we weren’t worthy enough to “succeed” after all.

We must know what we need to overcome in order to overcome it. This self-reflection is the most challenging, as it requires vulnerability and honesty. I’ve found it helpful, and I believe these fears deserve to be challenged—especially if they cause you harm or hold you back from something you truly desire.

Still, it’s important to be as kind as you are honest with yourself. And to remember that people around you who are as kind as they are honest make for very good sounding boards.

The moment you’re ready

We can’t be fully ready for what we cannot predict. We can prepare as much as we want, but life is unpredictable, and so is starting a business. I know I am ready to jump when the desire to see an idea come to life is greater than my fear of the unknown. It’s subtle, but eventually the longing becomes hard to ignore.

Preparing to jump

Jumping doesn’t necessarily mean running off a cliff unprepared. My parents planned their risks as pragmatically as they could. My mom kept her jobs, making rope for my dad to hold as he scaled down the side of the rock face. She carefully climbed down, going back to school part-time after my dad had built a foundation high enough for her to survive a fall, if one should happen.

Many new entrepreneurs work day jobs until their businesses have enough momentum that it makes sense to stop. Even in the beginning months of Beaucoup, I took a few design jobs on the side, just in case. Why choose to jump the whole way down if there’s a rope?

The questions never stop

At all stages of your business’ growth, there will be new questions to ask—to keep asking. Ask for advice from people who have been where you are, and don’t spend energy reinventing the wheel. Ask about the things you don’t know, and about the things you don’t even know you don’t know.

But also, consider the source. You wouldn’t necessarily take health advice from your lawyer, nor legal advice from your doctor. People have different experiences, scars, motivations, and levels of expertise. Listen, examine, glean what you can, and leave the rest if it doesn’t serve you (my advice included).

Plan for help

A business advisor once asked me to draw three lists: first, things you’re great at and love doing; second, things you do well but find draining; and third, things you’re not great at, period.

He suggested hiring others for those things in the third list immediately; eventually hiring for the second list once finances allowed; and focusing my energy on the first list, as it would be my greatest contribution to the business.

Define your walk-away point

The more we invest in something, the harder it is to walk away from, even if it sometimes pushes us to worse outcomes. This is essentially what’s known as the sunk cost fallacy. It’s especially tricky to navigate when you’re into the business already. Objectivity is hard to achieve when markers of success are subjective, or when you are very stubborn like me.

Before opening Beaucoup, I defined a point at which I would be willing to walk away. For me, it was an objective marker of financial loss over a certain number of years of investment. Even if I had reached that marker, I might not have chosen to quit—but it gave me peace of mind to know that I had defined exactly what I was willing to sacrifice, and that I was not obligated to give more. I allowed myself permission to walk away when that marker was reached, and also gave myself a built-in checkpoint.

Nothing to lose

You’ll never know everything, even after asking all the questions you can think of. There will come a time when you just have to jump—or not. You can’t wait forever, or you’ll spend your whole life waiting, and waiting will decide for you.

You can only make a decision based on the information you have now. There will always be unknowns. In the end, the choice is about whether you trust yourself to navigate the inevitable twists and turns that will come.

And what if you do fail? Would it still be worth a try?