Is your plate full these days? Many of us know the feeling. Work–life balance barely scratches the surface; then there are family, friends, health, finances, and—somewhere on the to-do list—things you just plain need and want to do to be a happy human. Adulting is a lot, even or especially for those of us with an aptitude for it. We can easily take on a ton of roles and not be aware of how far we’re stretching until we suddenly realize we’re living at the center of a whirlwind.
Enter the WINGMAN. Kimberlie Dykeman knows how it is—and how to handle it. She’s spent over 25 years as an entrepreneur studying and mastering a wide variety of problem-solving skill sets that most of us don’t have at our fingertips—but when we need them, we really, really need them. Her roles include estate manager, lifestyle coach, personal assistant, private concierge, real estate salesperson, and a range of things that are hard to categorize and perhaps understood by considering her nicknames: Troubleshooter, Connector, Miracle Worker, Confidante, and Fixer. Through her company WINGMAN Enterprises, Dykeman’s calling is making your world a better place, smoothing the wrinkles from your life, and facilitating your success in ways you may only have dreamt of; she’s in the business of abolishing stress and chaos wherever and whenever they pop up.
“Lots of people have one or more trusted wingmen in their lives: best friends, confidantes, hairdressers,” she says. “It’s wonderful to have friends and loved ones like that, but there are times when a situation arises that calls for something more.
Photo by Brad Switzer.
Photo by Billy Pasco.
Your people may be a little too close to be objective, or maybe what you need is outside of their area of expertise. That’s when Wingman can be the magical ingredient that can turn your struggles into solutions.”
A globetrotter since completing studies at Binghamton University, her entrepreneurial journey began in Austin, TX, where she started a personal training business. Her empathetic nature clued her in to the reality that there were situations facing a lot of her clients that physical fitness alone wouldn’t fix. “I found that many people who sincerely wanted to get fit and strong were also dealing with challenges and hiccups that 12 more pushups or lunges wasn’t going to resolve,” she says. “There might be underlying things that brought them to where they were in the first place, things that were impeding their ability to stick to a training plan.”
Like many a personal trainer, she found herself hearing about a lot of these peripheral issues in the course of any given day. “I knew there was more to it than I could do in a strictly fitness-focused role,” she says. “So I went through months, probably a year, of asking questions and doing all sorts of research, and then I segued into lifestyle and stress management coaching. I developed my own methodology that transcended the body, because I’ve always believed our lives involve so much more: body, mind, family, career, and role in society. For me, the hub of that wheel is my spirituality and my relationship with God; but the basic methodology—which has developed through several iterations and just keeps growing—equipped me to
look at what was going on in those pillars of a client’s life and assess their situation. To say, okay, let’s figure this out. Let’s address the people, the places, the things, and the habits that might be holding you back, and find the solutions you can act on that will lead to solving problems, removing stressors, and getting you to your goal.”
Dykeman initially found that the American Council on Exercise didn’t even think lifestyle coaching was a thing. “They didn't even give me the time of day,” she says. “They said, ‘We don't know what you're talking about. This is such a silly topic!’ I said, ‘Well, it's going to be huge someday.’ But I didn’t bother trying to convince them. I built out my methodology, and that led me into a full-blown coaching business.”
A stand-out in Austin’s tech space, Dykeman coached executives and startups on their quests for success and happiness, and eventually bloomed into a motivational speaker, published author, TV host and producer. During her time spent in places from Los Angeles to Boston to the Philippines, Kimberlie kept building her techniques along the way and finding the common-ground issues that make life worth living. “You assess the situation, marshal your tools and resources, make a game plan, and figure out what to outsource, what to do yourself, and how to fit it all together,” she says. “For me, I know I want to work as smart as I can, think clearly, feel strong and healthy, and lead a happy life. So, over the decades, I’ve been crafting a simple methodology from which I can extrapolate that to fit just about any situation you might be facing.
Photo by Billy Pasco.
"My whole goal is always to be of service, to motivate, educate, activate and execute for people so they can have a better life with less stress and focus on what really matters to them." – Owner Kimberlie Dykeman
Photo by Melinda Gimpel.
Photo provided by Kimberlie Dykeman.
My whole goal is always to be of service, to motivate, educate, activate and execute for people so they can have a better life with less stress and focus on what really matters to them. I help people sort priorities, deal with the things that are keeping them up at two in the morning. I think it’s almost always easier for someone else to see a path forward out of the chaos, to mitigate the stress, and focus on the goals. We get granular, make a game plan, and take it from there.”
Eight years ago, facing a complicated health crisis, Dykeman came home to heal and found that plenty of us right here in the Hudson Valley needed a wingman too. Mid-pandemic, she reinvented herself and launched her multifaceted business, WINGMAN Enterprises, and she feels as though the move has kept her in sync with her own sense of the divine and her own life path. “Being seriously ill—I couldn’t drive, my memory was shot, I could barely stay awake for more than a couple of hours—and having to shut down my entire life out there and get home was a big lesson in applying my techniques to my own life. Then, as I healed, I didn’t want to commute to the city every day, so I started looking at what I could do up here. I found there were people juggling second homes, family obligations, big decisions of all sorts. So, I inserted myself as estate manager and personal assistant, and it really calls upon my whole skill set, which is constantly expanding.”
Every day brings fresh situations. What do you do when the pipes burst in a sixth-floor walkup and the owner is in Egypt? How do you handle a blended family Christmas across three separate homes? How does one best manage a squirrel invasion, an aging relative’s needs, or an offspring’s college logistics in a faraway state? “You name it, I’ve dealt with it,” Dykeman says.
Ghent House, One of Dykeman's Concierge Properties.
Photo provided by Kimberlie Dykeman.
“It amazes me, the variety of scenarios people have entrusted me with back here in New York over the past several years. But I’m blessed with “mini-me” helpers, connections and resources all over the country, from all walks of life, and I just keep cultivating more, globally and locally. It’s amazing how much we have right here. I love the Hudson Valley, and I can tap into amazing, seasoned vendors, contractors and experts, and it’s such an honor to be trusted in my hometown.”
She’s developed a custom that she believes helps weave the fabric of the local community and build neighborly networks. “About once every quarter, I have what I call the Wingman Social; I invite my network to come get together for a meetup, maybe at Greig Farm for a beer or Mighty Donuts or some other wonderful local spot, so I can just love on them and thank them and they can see for themselves what a wonderful community this is and further build their own relationships.
That’s the core of Wingman, really; I just come at every situation—physical, mental, spiritual, professional—from that place of love. That, plus decades of experience, helps my clients to ultimately work smarter, think clearer, feel healthier, and live happier lives.”
wingman enterprises
Based in Rhinebeck, available worldwide
310-500-9587,
grabyourwingman.com
