6 Pieces of Advice That Make the Jump Possible

Abigail Ogilvy Holden
When to Jump
Published in
4 min readApr 28, 2016

I left a job and steady salary to take time off and find a way to follow my passion as an owner of a Contemporary Art Gallery. In the year I spent opening my business, I found myself in more unexpected scenarios than I could have ever imagined. My motto became: “Don’t plan, close your eyes and jump, and enjoy every moment of it.” In just 14 months between leaving my job and opening the gallery, I worked as a cashier at a family run hardware store, became the General Manager of two Italian restaurants, opened a pizza shop, brushed up on my Spanish, learned to appreciate homemade pasta, lived in New York, and made friends from all walks of life. The journey isn’t always planned, so open your eyes and allow the unexpected come your way.

1. Be a cashier at a hardware store.
Redefined for you: go outside of your comfort zone. I was walking down a street in my neighborhood and saw a sign outside our local hardware store that read: “Hiring for cashier.” I didn’t want to burn through my savings so I walked in the door and applied. My college degree did not teach me one thing about working as a cashier, I learned mistakes are ok and hasps are in aisle 12. Watching my boss run his small business taught me more than any level of schooling could have.

2. Being tough as nails isn’t tough enough.
Shortly after picking up work at the hardware store, I joined the team as General Manager of two nearby Italian restaurants. Major life lesson: people love to complain. There is a fine line between good customer service and deciding when to hold your ground and defend your business. The respect I have for the restaurant owners out there is through the roof! But fighting for your small business every day of every week of every year is what it takes to survive (side bar: yelling is ok, punching is not). As a female business owner under the age of 30, I have to fight harder than ever to prove I am a capable businesswoman in the art space.

3. Meet new people (extra points if you can do so without an app or email)!
I met endless people in the year I jumped. While I wasn’t manning the cash register at the hardware store or firing my pizza delivery boy, I was out networking. One of my now closest friends, Meredyth Moses, is in her early 80s, ran a gallery for 30 years, and we met at a gallery exhibition opening through a good friend. She is one of the hundreds of people who supported me in my journey. Allow it all to happen!

4. Don’t forget to eat.
Really simple, but easy to forget. 3 meals a day. You need it for all of the energy you will use up on the jump. Underlying goal: Take care of yourself (sleeping, eating, and exercise are a must).

5. Keep learning!
You will never know it all. Take an online class, ask people questions, get lunch with a stranger and find out what they do. Learning doesn’t just mean going back to school, I moved to New York to learn more about the gallery business at Sotheby’s, but spent afternoons exploring the arts first-hand on my own. You never know what piece of knowledge could forever change your business model or be a catalyst to your success.

6. Be an 8-year-old.
I am a total kid inside. I love Sour Punch Candy straws, watching Disney movies, and wearing Chuck Taylors. No one sees this side of me at work, but it’s what keeps me constantly energized. It’s freeing to remove the shackles of adulthood and quietly do something that reminds you of being a kid. Ride a bike, climb a tree, play video games… Those small moments will get you through your worst day jumping.

Abigail Ogilvy Gallery just reached 6 months in business, and we are still going strong!

When to Jump is a collection of people, places, and ideas relating to when to go do what you really want to go do. For more stories like this, sign up for our occasional newsletter here. You can follow When to Jump on Facebook, Instagram, and Twitter.

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Abigail Ogilvy Holden
When to Jump
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Abigail Ogilvy owns and operates a contemporary art gallery in Boston’s South end, called Abigail Ogilvy Gallery, featuring early career, emerging artists.