What 26 Years and Two Hurricanes Taught Me About Starting Over

Do you have a business plan? Nobody asked me that when I was 24, which was lucky, because the honest answer was no. I’m the founder and principal designer of HSH Collective, a design studio and showroom on Anna Maria Island, Florida, where I’m a fourth-generation resident. Twenty-six years in, I lead a team of nine designers, I’m married to an antiques dealer, and I have a son. If you’re rebuilding something right now, whether that’s a business, a house, or yourself, I wrote this for you, and I’m not going to tidy it up. The messy parts are the useful ones.

No Business Plan, One Nokia

I never planned to own a company. After design school I worked for an interior designer in Sarasota, and I loved it. It was an old-school firm where she was the face of everything, and I didn’t mind. Then one day she told me she didn’t see a future for me as a designer and thought I’d be better in management. I gave my notice with no idea what came next.

The phone started ringing as soon as I walked out the door. Soon I had 16 projects running out of the guest bedroom of my 1,200 square foot house. I come from a long line of developers and contractors, so I sold them blocks of my time, 15 or 20 hours at a go, and promised to get a set amount done.

My first client was a whip-smart businesswoman I still learn from. After our first meeting she asked me to email her our working terms, and I sat in my car holding a Nokia with no website, no contract, and no email address. I called my brother-in-law, the techie in the family, and begged. Then she bought a second house, and I sent her an $80,000 window treatment proposal. At four in the morning I sat straight up in bed, because that number was close to what my own house cost. It went fine. I wake up at four to this day.

My first employee came from my old firm. I told her I had no work and couldn’t pay her. She said she was coming anyway. She still works with me part-time, and I tell her regularly that I’m not sure I can afford her.

The Boss I Didn’t Want to Be

For years I was a pushover with a temper. I ran hot, then cool, then hot again. I let things slide, then got resentful that nobody was doing their jobs, when I hadn’t let them do the jobs in the first place. During COVID my team was me and two other women, and both of them left. I wasn’t being my best boss, and I hate calling myself a boss at all.

A mentor once told me to be careful of the business I build, because I’d have to feed it. I finally understood him. I started working with a positive intelligence business coach to figure out how to hold real authority without losing the caring, contractor-friendly reputation I’d built my whole career on. I’m a controlling person by nature, so letting my designers own their work and make calls I’d have made differently remains the hardest thing I practice. We own the mistake, I ask what the lesson is, and we move on.

The company had to grow up too. It started as Jessica Holmes Interiors. After I married and had my son, I knew it needed an identity outside of just me, and it became HSH Collective. I also quit hiding my personality at work. I came up in an era when you proved you were serious by being boring, and now my team teases me about emails that sound exactly like me. I’d rather that than sound like I graduated from Princeton.

Two Hurricanes and a Conference Table

Then Helene and Milton hit the island back to back. The water took my home, my 97-year-old grandmother’s home, and our office and showroom. I was born on this island, and I still can’t talk about it without tearing up. We lost every pen, tape measure, and sample.

The first thing I saved was our conference table, the one with the metal base. I set it up in the back of the new space, a concrete slab with white-painted walls and the water lines on the wall, and threw some chairs around it so my team could be together again as fast as possible. I kept all my team’s paychecks and bonuses intact, and I’m fairly sure I’d lost my mind. We came out with a showroom three times the size of the old one. It also took a lot out of me, emotionally, physically, and mentally, and I won’t pretend otherwise.

Here’s what I’ve learned about myself since. That first client taught me that discounting your fees means discounting yourself, and I’d rather give work away than discount it. I can also say no. Not long ago I walked away from a project for a dear old family friend because our values didn’t line up, and I slept well. On a seven-mile island, that was a big moment for me.

What’s Still on the List

Plenty. I’m writing a memoir about my 26 years in this industry. I create the fragrances for my candle line myself. I’m building toward a lifestyle brand alongside my husband’s antiques business and our growing presence at the Round Top show in Texas. I’d love for this company to run without me sitting in every room. And I keep ending up mentoring other women who find their way to me, which I love.

If you think you’re too scared or too late, I was scared to death at 24, and all I had was a Nokia. Set your price early and hold it. Find the mentor. Hire the coach sooner than I did.

If you’re in the middle of your own rebuild, I hope this reminds you that you can start late and without a plan. If you’d like to see what grew out of that concrete slab, come visit HSH Collective on Anna Maria Island whenever you’re nearby.