Episode 20: How did you prepare to jump?
To create space for Jackie to write her upcoming book, To You Who Wonders – an advice column meets memoir – she will be reading from her past column, Ask JKE, for Virtuvi's Natural Habitat Magazine.
This week, she is answering the question "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?" She reflects on the answer she wrote so many years ago and shares her reflections, what has evolved since, what she would have written differently or what she was experiencing at the time she wrote it.
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We hope that you get something helpful out of this conversation. If anything, know that you’re not alone. You see, we all struggle, mourn, yearn, question, laugh and cry. No matter our age, background, or titles, at our core, we are all not so different, You & I.
Make sure to listen until the end to hear the question we will be diving into on the next episode. And if you feel inspired to respond to this asker and are interested in being a guest of this episode, or if you have a short word of wisdom for them, write to us on the contact page on youandipodcast.com or DM us on Instagram at @youandi.podcast.
Episode Resources:
Jackie Kai Ellis: Website / Instagram
Vitruvi's Natural Habitat Magazine: Website / Instagram
You & I Podcast: Website / Instagram
Resources on finding trusted professional help can be found here.
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The following transcript was automatically generated. Please be aware that it may contain errors. Thank you for your understanding.
Welcome to You and I.
I'm Jackie Kai Ellis and it's my genuine hope that through sharing our most vulnerable stories we know, in the moments where it matters so much, that we're actually not alone. It needs to be said, I'm not a professional, just someone with some personal experience to share. I do hope this is helpful, but as always, take the advice that resonates and ignore what it doesn't. And don't hesitate to seek out professional help through trusted source. We’ve provided links on our website in case you need them..
For the next couple of months I’ll be focused on writing my upcoming book, To You Who Wonders, an advice column meets memoir. So to make space for that, I’m sharing words from my past advice column, Ask JKE, one I wrote for Vitruvi’s magazine, Natural Habitat.
It’s been a few years since I wrote them, some advice is timeless, and yet I’ve changed so much too. I’m curious how my advice will be different now that my perspective is different. So in these episodes, I’ll read out the column and also share my reflections, what has evolved, what I would write differently or what I was experiencing at the time I wrote it.
I hope you enjoy the Ask JKE series.
Today, I’ll be reading the column I wrote in answer to the question, “How Did You Prepare to Jump?”
They write:
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? -KHJ
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?
When I wrote this, it was in the middle of the pandemic, and not in the midst of a tenuous financial climate where jumping would be that much scarier than it would be, even in the best of scenarios.
I do remember before deciding to open Beaucoup, paralyzed by fear and knowing the only way through was to look my worst-case scenario in the face. I allowed myself to voice the worst: going bankrupt, having to move back in with my family in my mid-thirties, and having smug faces gloat the words, “I told you so.” Though, after I had said it aloud, it didn’t seem so bad after all. I could survive bruised egos and ruined credit.
I reasoned that at 35, there was so much time to build a new career, or go back to an old one if things didn’t work out. And even if those back up plans didn’t work out, I was very hirable and so would get a job at starbucks (for their benefits package) and work my way up from there.
It gave me a sense of security knowing that I had my eyes open. That I could look at all the risk and decide with each potential pothole or cliffside, whether it was a sacrifice I’d be willing to make.
I remember planning not to have any income for 2 years. I planned out what I’d do if it went longer than 2 years and if I’d be willing to sell my apartment to stay afloat. I imagined where I would shower and sleep if I did. I decided which sacrifices were worthy just to try, just to have the experience of building my dream and how much loss would be too much loss. And in looking soberly at it all, I wrote down a list of when I would give myself permission to walk away, and I planned which day I’d look at this list.
I never needed to look at this list. My dream had come true. The bakery was financially successful and I never had to consider many of those sacrifices.
But some of the sacrifices, the emotional and personal ones, wore me down more than I cared to admit and I found it increasingly harder to tackle an ever-growing list of responsibilities in the midst of extreme burn out. The one thing I hadn’t accounted for. I never thought the passion for my dream would wane, it didn’t even cross my mind.
And because I never clocked out and I never stopped thinking about the business. The to-do list never stopped getting longer and heavier. Staffing and administration, the quality control, the complaints and constant equipment repairs …skills that still don’t come naturally to me…as years went on, it had become harder and harder for me to feel excited or grateful for something that was once my dream.
I thought there was something wrong with me, that maybe I was being flaky or spoiled, even. I felt guilty about it. I had imagined my community centered around the daily routine of the bakery, I had imagined my whole life devoted to it. It felt like I was betraying my own dreams. So I pushed those feelings away, pushing through, hoping it was just a phase. But the longer I ignored these feelings, the more they intensified and I ended up making excuses not to be at the bakery, which only hurt the business and my team. But after it opened, something inside me changed. The experience of opening the bakery, itself, had changed me. Deep down inside I had already moved on, but I couldn’t leave because I wasn’t yet able to admit that I was drowning in what was now someone else’s dream.
When I could no longer bear to live a life that didn’t feel genuine to me, I finally allowed myself a new thought. I allowed myself to change. I gave space for evolution. I accepted who I was, and though it may not have been normal by society’s ruler, I let go of who I and everyone else thought I was supposed to be: someone living her dream, and embraced who I was: someone who dreams.
I am still learning to accept that I won’t follow a linear path. That I am not necessarily bad at follow-through but that I will naturally move on when I’ve learnt everything I need to learn from any one experience. I am still embracing that maybe my goal is not to make something successful in the eyes of others, but that I want to spend my life learning – learning who I am, and honoring that.
I give this information because I want anyone who hears this to not only feel empowered to create what you dream, but also to feel permission and freedom to leave your dream, to evolve, to change your mind, to learn who you are by trying something and learn who you’re not, to dream again, to jump again, and again, if you so choose, with open and compassionate eyes.
I hope you enjoyed this episode in the Ask JKE series. I hope you got something helpful out of this…if anything, know that you’re not alone. You see, we all struggle, mourn, yearn, question, laugh and cry. No matter our age, background, or titles, at our core, we are all not so different, You & I.
If you have a question you’d like me to explore either on the podcast or in my upcoming book, To You Who Wonders, write to us on the contact page on youandipodcast.com or at toyouwhowonders.com.
If you enjoyed this episode, like and subscribe to our channel, which helps others who might be interested, find us. And feel free to share this episode with someone who may find it helpful as well. Thank you for joining us today. I’m Jackie Kai Ellis, this is you and I.