Authentic Conversations with Entrepreneurs Episode 13: “Sail On” with Hayden Orme

In this episode of “Authentic Conversations with Entrepreneurs” I spoke with Hayden Orme, CEO Strategist & Consultant and Owner of Handled. By Hayden & Co. Hayden shared her story of how she’s “Sail(ed) On” through all the ‘rough waves’ in her life and business, and still growing it 300% year-over-year between 2022 and 2023!”


Katherine Morales: Hi, everyone. Making sure I was connected there. Welcome to Authentic Conversations with Entrepreneurs. I’m thrilled to have Hayden Orme here in our 13th episode. Hayden is a CEO Strategist and Consultant and captain of Handled. By Hayden & Co.

Before we kick off, I just always like to say, what the heck is an authentic conversation? What is the whole mission of this show? I describe authenticity as the Good & Growing™. You can tune into any show anytime that’s going to tell you all the successful things and the how-tos and the tips, and that’s not what this is about. This is about the journey of an entrepreneur, today Hayden. Thank you for being here.

Hayden Orme: Thanks for having me.

Katherine Morales: Of course. It’s about sharing your authentic journey through entrepreneurship. We all know it’s not all glorious and sunshiny days. There are bumps in the road, or I should say waves in the sea in this case. Sometimes tidal waves or undercurrents, but we’ll get to that. Without further ado, let’s talk about today’s topic, sail On, and what does that mean to you, Hayden? I said captain, so tell me more about that.

Hayden Orme: Well, it’s a term originally used as a captain on boats, right? You just sail on, head for the shore, your destination, whatever, but it really applies so much in entrepreneurship. There have been so many challenges. We all have so many challenges.

Katherine Morales: COVID, if you didn’t, and then 2020 hit.

Hayden Orme: Global pandemic. That’s all.

Katherine Morales: Yeah. Just a little pandemic.

Hayden Orme: Yeah. I launched my business within weeks of needing emergency life-saving surgery and a global lockdown.

Katherine Morales: Oh, my God. Was that a tidal wave?

Hayden Orme: I think it was more like a tsunami.

Katherine Morales: I’ll stop. I’ll stop.

Hayden Orme: A friend actually used this analogy with me because I was like, I’m recovering from surgery, I had to have my gallbladder out, it was locked down. It was a rough time for everybody.

I just was like I’m just constantly putting in the work, putting in the work, putting in the work. I’m not seeing that ROI. I’m not getting traction. My business isn’t taking off. Maybe I shouldn’t be doing it. I started to have all those limiting beliefs crop up. My friend was like, “You’re just planting the seeds. You’ve got to let your garden grow. You’ve got to give it time.”

Katherine Morales: I love it. We’re going from the sea to the garden. Okay. Yeah.

Hayden Orme: Ocean, garden. That was really true. I just had to pivot and change course. And then, by October of that first year, I really did start to get traction. Even then, so I’m building my business, I’m bringing in clients. It was one thing after another, which it can be for so many of us sometimes. We’re still in COVID, life is happening, all of a sudden everyone’s working from home with kids and pets. We’re not meant to be operating that way. I really had to embrace, all right, just sail on. I’m still going for the destination, but I might have to take a different path to get there, a different course to get there.

Katherine Morales: Wait. Back up a second. You actually are, or you sail boats and you were or are a captain, right?

Hayden Orme: Yeah.

Katherine Morales: Sorry. I just was going to say, do you remember going, “Hey, I’ve faced this sea before. It’s not an ocean, it’s a business.” I’m sure you faced rough waters before. Is that where it came from?

Hayden Orme: Yeah.

Katherine Morales: Okay. The garden thing, yes, but …

Hayden Orme: I’m a licensed Master Merchant Mariner 50-Ton Captain. It’s kind of a mouthful. I have my little captain hat. I should have it on.

The ocean and sailing is my number one passion. I love it. I used to work on boats full time. I used to run a charter company. I was professional crew, professional captain, and so many of those skills are so applicable in life and business. I would get flown to a destination that I’d never been to before to sail a ship or sail a sailboat from point A to point B, usually internationally with people I’d never met. You’re in very tiny quarters at sea, no sight of land for a week, 10 days, and you have to make it work. You’ve got to get the boat efficiently to the destination, in good shape for the owner.

Katherine Morales: No choice but to sail on.

Hayden Orme: You hit storms. Sometimes you have to replot your course and go around a storm. It’s really a good analogy for business and entrepreneurship.

Katherine Morales: Hence the ship in your logo in the background there.

Hayden Orme: This ship is actually my dream sailboat. It’s actually a mockup of a blueprint of a Hinckley Sou’wester sailboat, which is my favorite boat. One day I will have one, hopefully. That really is authentically me in my branding.

Katherine Morales: I want to go back for a minute. You talked about you started your business basically at the top of the pandemic or right before. 2020.

I know several other business owners that did that. I think it has to be so interesting. You said the notorious word, the pivot. Was that a term used in shipping? You said there would be a storm. Do sailors use that? Do you go, “We must pivot the ship?”

Hayden Orme: I think of the Friends episode moving pivot. Not really. It’s more we have to change course. We have to put in different waypoints. Pivot isn’t really a nautical term.

Katherine Morales: You’re always educating me on this stuff when we talk, Hayden.

Hayden Orme: It’s more like tack or gybe, but you change your course.

Katherine Morales: I love that. Is it you discovered that in 2020 and been sailing ever since smooth waters? How has it been navigating, I’m going to roll with this, navigating through the first three years in your business now? Congratulations!

Hayden Orme: Thank you. Being an entrepreneur is very humbling. I came from corporate with that sense of security and I’m so glad that I’m an entrepreneur 500%. But it is hard, and I think everyone watching this can relate. There are days where you’re just like, “Should I even be doing this mean? What am I doing?”

Katherine Morales: That’s a normal thing. Yeah. It’s okay to feel that way.

Hayden Orme: It’s part of life, part of being an entrepreneur. And then, those challenges, those doubtful times, those storms are really a chance to just regroup, look at the chart like, “Okay. I still want to get here, but maybe I have to take a different course to get there. What do I need to do?” We’ll be in business three years in April, and it’s been an amazing three years and a very tough three years. I personally have gone through a lot of challenges and I had to have two more surgeries. I ruptured my Achilles. Right before rebranding and relaunching my company last February, which you were an integral part, I had two surgeries for a ruptured Achilles tendon. That really knocked me down, and then I got COVID in May and it was one thing after another. I am a recovering perfectionist. I have a proclivity for just wanting to handle it by Hayden, like, “I got it.”

Katherine Morales: Yes. The rebrand went from Handled. By Hayden, and we added the & Co, right?

Hayden Orme: Right. Those sort of challenges that really knocked me down made me realize more than I already … I know that I need to rely on my crew, but I have an amazing crew behind me with whom I would not be where I am today. It reminded me, and they remind me that really to embrace being an empowered CEO, I have to rely on my crew and I have to let them do what they do best. Sometimes, that requires taking a step back and actually healing from surgery, taking care of myself, healing from COVID and letting them support me. That’s hard, that’s vulnerable. When I work with clients on this, I say we hold a lot of space for the vulnerability around opening up your business to bring in new people because it’s your baby. It’s very personal when it’s your business.

Katherine Morales: I’m sorry. Go ahead.

Hayden Orme: No. Yet when I did, especially last year, I brought on an operations manager who’s phenomenal, and just really relied on my crew more, even with all those storms and tsunamis, I managed to grow my business 300%. It was really an incredible year.

Katherine Morales: I just have to say, this isn’t the case with everybody I talk to, but I’ve been with you on a lot of that journey, Hayden, and I just think I totally relate to you on a recovering perfectionist. I think a lot of entrepreneurs are, and it’s built in. You’re the captain, you’re the CEO, and you have the vision, you know which way you want to grow your business. I love how you were talking about you went to these remote destinations and you’re in tight quarters with people you don’t even know. It’s kind of like that. When you begin to open up to working with a crew or even a VA or an assistant, I will say Hayden has educated me, so not the VA, the executive assistant. There is a difference.

When you open yourself up to that, you and I know my own journey of letting go of perfectionism and that, it feels like even though it’s a virtual relationship, you feel like you’re in tight quarters. It’s your baby. I just love that visual that you’re describing. I have to give a shout out to some of our friends who are on here, Brian, Hannah, Brittany, thank you so much. I want to mention one of Hannah’s comments because she said at one point … What’d she say? You’re in the lower deck or something. Wait. Yeah. Below deck over here. It made me think of something.

I had this aha several years in the business, and I think I’ve told you this story, is we all think it’s the corporate ladder. You talked about corporate. I want you to hit on you reached the top of the ladder and you chose entrepreneurship. Can you share a little bit about how it turned from this climb of a ladder to a sailing and charting path to ocean and the difference there?

Hayden Orme: Yeah. I left corporate in late 2019. My last position was supporting, really running the whole office for the chairman and CEO of a Fortune Five company at the time. That was the highest I could go unless I transferred to Fortune One.

There was nowhere else to go, but up. I’d supported several C-suite executives. There’s just this moment I always remember. I had this gorgeous corner office looking out over the harbor at my desk, and I was just sitting there holding back tears thinking this can’t be it. This can’t be all that I’m doing with my life.

Katherine Morales: You literally had that upper level, nice, beautiful real estate corner office, nice pay, but the irony is you’re the captain looking out at the ocean.

Hayden Orme: Literally looking out at the ocean.

Katherine Morales: Sorry. I didn’t mean to interrupt, but I was hoping you would tell that part because I remember.

Hayden Orme: Literally looking at beautiful boats go by. My office was over a very exclusive marina where mega yachts would come and dock in the summer. I’d look down and I would just see the crew polishing all the windows, whatever. Not that that’s exactly what I wanted to be doing, but I’d see them take off, I’d see the sailboat go by and just be like, “That could be me.” I had the financial security, I was making the money, I had the job security, and I was really trying to figure out how to leave. I just was so unhappy and so burned out.

Katherine Morales: No time for you to actually be out on the ocean, right?

Hayden Orme: No. I got all these invitations. “Can you crew? Can you sail?” I can’t leave my desk. I was on call 24/7, 365. When I left, I left because my CEO retired and I was given the option of taking severance and exiting the company as a layoff or relocating for another position within the company again. I’d already relocated twice across country twice in three years. I didn’t want to relocate again. I was like, “This is my chance. If I don’t take this, I’m never going to.” I took the severance and didn’t look back. I talk about this detox I went through where I just had this stress detox. My body was releasing the burnout. I started to interview for jobs and I was having visceral reactions on the interviews and I was like, “I can’t do this again. I just have to embrace what my gut is telling me that I need to work for myself.”

Katherine Morales: Really, it was like, “I have to embrace it.”

Thank you so much for sharing that. I literally got goosebumps as you said, “This is my chance.” I think that every entrepreneur in whatever words or shape it takes has that moment where you decide to take the leap or you decide, “I want to not be in this beautiful office and I want to go out on the ocean and see what there is.” But I think it’s such a great example of we can take that leap, but even when you’re in entrepreneurship, you can feel at the bottom of the deck. You can feel like, “Where is the sunlight? Get me out of this.” I think that through my own journey, and I think you would agree Hayden, that you have to almost shake off that corporate shit. I knew I was going to talk like a sailor at some point. Sorry. It just happens with us.

There’s no other word for it. You got to shake it off because I think we’re always in comparison, but when you’re sailing a boat and when you’re operating your own business, it’s not about … I mean, yes, look out so you don’t collide with other boats, but it’s about charting the best path for you. It’s about saying, “Okay. I know how to navigate this ship.” I keep going with this. I’m not a sailor so I shouldn’t go with this, but ride with me. I shifted from I should be here, success looks like this, to float along it requires you to let go of that upward movement and the forward movement instead.

Hayden Orme: Yeah, absolutely. This analogy just came to mind. It’s human nature to compare ourselves to others, even though that’s not great, but we can all slide into that sometimes.

When I’m racing sailboats, I’ve done a lot of racing in my life, an analogy I think of is there are marks you have to round before you cross the finish line, and you have to round those marks without crashing into them. But different boats will take different courses to round the marks. They’re doing it based on where they’re positioned, even if it’s a few feet of difference in the water. There might be a wind line over here. Each boat has its own unique circumstances surrounding the course it’s plotting to round that mark.

We’re all rounding maybe the same marks or trying to reach the same goals, but we’re doing them in the way that works for us and our ship and our crew. It’s not about crossing the finish line, it’s about the journey and hitting the goals you want to reach, but it really is what works for you individually and not, “They’re doing this. I should be doing that.” Well, they’re doing that, but they’re also over there on the water and the wind line over here is different. It really is about just stay on your own ship.

Katherine Morales: I just get so smiley. It’s just a natural flow, sorry, how entrepreneurship is … I haven’t done a lot of sailing, even though I grew up in Florida, it was central Florida. We became friends through COVID. We began working together, and literally it’s been all virtual, but one day I’m going to get on a ship with you. That’s going to happen.

Hayden Orme: One day that’s happening. Yeah.

Katherine Morales: I just love all our conversations of how truly I relate to how you share the entrepreneurial journey through some of your lessons operating boats and races. It’s just beautiful. It’s beautiful. Thank you for sharing it. Okay. We’ve been swimming in it for a little bit. For the people here who might be struggling with the undercurrent, might be facing the hardships, I can’t help myself, sorry, I will stop, what would you say? What would you offer? I know there’s a lot of richness in what you shared so far, but what’s the one thing they should do next?

Hayden Orme: I would say really evaluate where you want to be, where you want to get, your goal. Goal’s goal, but this is totally not on brand, but a close friend says, “What’s the best way to eat an elephant? One bite at a time.” I think when one is overwhelmed, and I don’t know what to do next, it really is like okay, it’s not about crossing that finish line, it’s about what’s the next waypoint. Set small goals for yourself and rely on help. It does take a village. It takes a crew. We are not meant to be solopreneurs really. Technically, that’s not even a word. It’s an industry term, but a solo entrepreneur, really, you can only get so far and then you hit that plateau, that pain point past which you can’t really do what you want to do. I tell people, really evaluate the life that you want to have, and then evaluate your business model and how are they coming together. Are they flowing together well? Because you really want to structure your business to support the life you want to have, not the other way around.

A business isn’t the ship dragging you behind on a lifeline. You are on the ship. You should be at the helm steering the ship.,

Part of that is relying on a crew, relying on expert help and not trying to do it all yourself. As soon as I really embraced fully relying on my crew, as I shared it, and I went through surgeries, it really is about … I think just there’s a component of vulnerability too, really just identifying, “Okay. I’m ready to either ask for help, hire someone, evaluate what’s working, what’s not working, and maybe I still want to get there, but if nothing changes, nothing changes. Maybe I need to change my course a little.”

Katherine Morales: The destination is very true. However, you want to grow your business and yourself in your business. I think what you’re hitting on, and I love this because it’s the holistic approach that you take, it’s how do I want to feel when I reach that island? How do I want to feel and what did I give up? You were at that destination that you thought you wanted, and then it didn’t feel good. We leave these environments or we start our businesses, and a lot of entrepreneurs will say the word freedom, but then we build ourselves a box that we stay in and we don’t do the things we want to do.

One thing that is on brand beyond the elephant, I love that you asked this, is if you were on a deserted island, what would you take with you or what would you want with you? The first thing probably isn’t going to be my laptop. I love how you said the one thing, I think really not beginning with what do we want in business, but what do I want in my life with my business. I love that. Not dragging behind. Okay. Well, hopefully people are loving you as much as I love you, so they need to find you. Where could that be? If they want to connect with you, where should they go?

Hayden Orme: Yeah. Well, we welcome all inquiries and questions. Our website is, Within there, there’s the contact us page. People can submit an inquiry through there.

Katherine Morales: Get time with you or they book a call?

Hayden Orme: If they fill out that form, it comes right to us, and then they’ll get an email response that will have my booking link in it. They can book a call directly with me. If they’re also interested in marketing or other services, we can put them in touch with the right person internally, but it all starts with a call with me.

Katherine Morales: I love it.

Hayden Orme: They can email me directly, And then, we have our social media channels, Instagram, Facebook and LinkedIn.

Katherine Morales: That’s here on the screen. Here on LinkedIn. Don’t forget the little dashes between the handle by and Hayden. This has been amazing, Hayden. Since I started this show a year ago, I was like, “Got to have Hayden on. I got to have Hayden on.” You have such beautiful stories that I think every entrepreneur can relate to. You are such an inspiration to so many of us. Congratulations on growing your business through the undercurrents and all.

Hayden Orme: Thank you.

Katherine Morales: Everything you do. I think it’s interesting you are your client. Even though you had the crew at hand, you had to learn to pass things off to your crew. It’s just such a beautiful journey.

Hayden Orme: Everything I talk about, I’ve been through or I’m going through myself.

Katherine Morales: It is like that in business. Things hit you like waves to remind you, “Oh, this is what I’m doing and this is why I’m doing it.”

Hayden Orme: Yes.

Katherine Morales: Beautiful, beautiful story. Thank you so much for sharing it with us authentically.

Hayden Orme: Thank you.

Katherine Morales: I guess it’s that time. I’ll let you all go, but we’ll be back next month on February 16th at 1:30 PM ET “At the Heart” with Donna Cravotta. It has to be on theme with Valentine’s Day. That’ll be the topic so I hope you’ll tune in then. Check out Hayden. Everything will be transcribed and on my website, and of course, the recording here afterwards. Thank you so much to all of your crew and our friends and tuning in live. It’s been a true pleasure.

Hayden Orme: Yes. Thanks everyone.