After the Jump: The Importance of Taking Risks

by Grace Bonney

Neil Gaiman wrote, “If you dare nothing, then when the day is over, nothing is all you will have gained.” That sentiment is something I try to keep in mind on a regular basis when faced with the prospect of taking a risk. Risk is not only essential to staying relevant in any community, it’s one of the best (if not scariest) tools we have to constantly expand our base of experience, knowledge and confidence.

I’ve been thinking a lot lately about taking risks in business: why it’s so hard, why we avoid it and why, when we finally take one, the rewards feel so empowering. So I decided to dedicate this week’s radio show to the topic of RISK-TAKING. I had the pleasure of being joined by two women who know a lot about taking risks in business, blogger Gaby Dalkin of What’s Gaby Cooking and Crista Freeman, co-founder of one of my favorite ice cream companies, Phin & Phebes. Gaby, Crista and I dove into the core of this topic, discussing examples of when risk-taking had paid off (greater confidence, new skills, getting what you actually want) and how to handle when risks don’t end well (hint: build a support system). Their insight and honesty was beyond helpful and I think whether or not you own a business, listening to their advice will be incredibly inspiring. Thanks so much to Crista and Gaby for joining me on air and to all of you for listening.

*If you have a story of risk-taking you’d like to share, please share yours in the comments below, I’ll be adding some of mine today, too. xo, grace*


Suggested For You


  • Twenty months ago I took the leap and opened the garage door. Literally. And I haven’t looked back. My tiny biz is housed in my 1927 freestanding three car garage. It is called The Fort@3512. I open once a week for a two hour event called, “Drinks in the Driveway” and the rest of the time, by appointment. I sell new(40+vendors) and vintage(my love) gifts and accessories. I started with a miniscule budget and a passion to make it work. People thought I was CRAZY! So glad I didn’t listen and made my vision a reality. Most importantly, I spent ten months planning this endeavor. It really paid off!

  • Probably my biggest risk was when I left my career as a business consultant.

    All of my life from when I was little I was making things, watching theater, reading – anything creative? I tried it. Music was the center of high school for me and I even started university as a performance major in the BMus program.

    But coming from a working class background where I was taught to be practical (no blame from me – I was the first person in my family to go to university so I didn’t have a road map at the time), I transferred to business school and ended up as a biz consultant. And I was good at it. Moved up the ranks, made good money (golden handcuffs for a while).

    Throughout I was still making, drawing, painting, playing music. Finally I got up the guts to quit. It wasn’t a dramatic “I quit!” but a very measured risk. I had money saved up, I had freelance consulting gigs lined up to tide me over and I knew what I needed to make and by when to break even.

    Best decision I ever did. And now I’m building a career as a food photographer.

  • Re-branding. Because we restarted an old company we just ran with all the old graphics, but it’s also 14 decades worth of design trends and offshoot brands. When you are small business and you wonder if you are going to make payroll every week, throwing a big chunk of change at an identity is really scary. I have no doubt that it will be the best investment we’ve every made (we’ll see at the end of the summer, fingers crossed) but it was so hard to pull the trigger. It definitely feels like a big risk on this end of it.

  • my life quote is ‘leap and the net will appear’ literally, as i followed my first passion in my 20’s and became a professional skydiver. that motto is embedded in my dna;
    -plan, make short term and long term goals
    -there is nothing to be afraid of. if it is failure, consider it a lesson learned and a course correction
    -go with your gut
    -trust yourself

  • thanks for your wonderful insights. Always inspiring. For me, it was quitting my almost full-time job and make ceramic + taking care of our little son. Turned out to be hard to merge the two, but now, 6 years down the line, I´m grateful that my friend stood by me and encouraged me to do it. Couldn´t have done it alone!

  • Thank you for taking the time to dive deeper into a topic that can become very buzz-wordy without the context of real stories and experiences. I’m learning that many times those “big” risks are made possible by small risks that you take along the way. Perhaps this is the “calculated” part of a risk? For me it is finding the sweet spot between analysis-paralysis and leaps of faith!