"Once you have come to the conclusion that this is who you are ... don't delay."
That's the biggest lesson Wynne Nowland, CEO of insurance brokerage Bradley & Parker, learned going through her gender transition in mid-2017.
Nowland started working at the medium-sized firm in Melville, New York in 1986 and held several senior positions before becoming CEO and chair in January 2017, just a few months before her transition.
During those years, Nowland buried herself in work to avoid dealing with her two personas: At work, she was Wayne, but inside — and occasionally around a selective group of close friends — she was Wynne.
"One of my friends says that the work was my mistress, because it was a way for me to pour a lot of frustration and resources in getting things done," Nowland tells CNBC Make It. "So from that standpoint, I guess it had some value."
From Nowland's earliest memory, she knew she was "different," but it took her a long time to label it. It wasn't until a few weeks after her 56th birthday in 2017 and four months after promotion to CEO that she had an "awakening" and decided she couldn't hide her true self any longer.
Nowland sent an email to her 70-person staff telling them that she had made the decision to transition her gender.
"I plan to begin working as Wynne starting this morning," she wrote.
Nowland also wrote emails to corporate clients and board members, making it clear that she planned to continue to lead the firm the way she had for more than 30 years.
The next time Nowland arrived at work, she was wearing a woman's pantsuit, pearls, a pair of Tiffany earrings and full makeup.
Her colleagues greeted her with open arms that day.
"I did not fully come out until I came out at work," Nowland says.
Nowland, 59, now feels more at ease at work and in her personal life. "I'm much more at peace with myself," she says.
Here, Nowland talks to CNBC Make It about her journey to her authentic self, how she successfully lead her team through her transition and more.
On transitioning while CEO: It was a 'progression'
Over two years, I had really come to a kind of an awakening that I needed to lead a more authentic life.
It was kind of a progression. At one point, if you had asked me "Do you think you'll ever do this?" My answer would have been, "No, never." Then at some point it became, "Well, maybe I could do this," to "I can do this" to "I'm going to do this."
What I realized was that, unless you want to lead your life calculating every minute of the day, there's really no way to lead dual existences. Mentally you can, but outwardly, the communities are too small.
For instance, if I was living as Wynne outside of work and I was at a restaurant on a Sunday night and a business associate saw, it would be all over the office the next day. It would not be the controlled kind of announcement that I would want to happen.
As for fears, you are concerned that people you care about are not going to accept you. You worry about [it] altering your business relationship in a negative fashion. That to me was the big unknown.
I know this is not the case for many people in my position, but honestly, people have gone out of their way, since that very first day I came into the office as my new self, to make sure that I know that they supported me and had my back.
There's been some negativity along the way. Whenever you put yourself out there, particularly with social media, you're going to bring out the factions that are not in favor of my kind of lifestyle. But really, those have been in the real minority.
On how she changed as a leader: 'In essence, this was always who I was'
I used to make the joke that I think I'm better off because I'm not bothering to juggle two personas. So I can really just put all my efforts where they're needed businesswise. And I've heard from many of the team members that they think I'm a more effective leader after my transition.
It's not like I took a pill four years ago and changed who I was. In essence, this was always who I was, I was just presenting a different persona every day when I walked through the door.
I think what has happened is that people feel more comfortable coming to me with issues than they might not have before.
On giving people time to adjust: 'There's an initial shock value'
No matter how you couch this, no matter how you talk about it, there's an initial shock value when you hear that somebody you've known for years as a male is now suddenly presenting female. You need to give people time to adjust to that.
I sent a variation of that same note I sent to all the team members to a lot of different people in my life, family members and even some of my favorite restaurants and my favorite butcher in my town. By taking a few minutes and sending them an email, or when I didn't have their email addresses, the snail mail, and telling them what's going on, you give them some time.
I do think that that I've tried in my life and in my career to do the right thing. I tried to do the right thing for my clients, for our insurance company partners and for our team members. I think that by doing that through the years, even when people don't understand what's going on or they need time to process it, they're giving me the benefit of the doubt.
On her biggest mistake: 'Don't delay'
I've had some parents of people in my situation reach out for advice and I always try to make the time for them.
My advice is consistent: I think it's important to avail yourself of the professional help that's out there to help guide people through what can be a confusing time. But once you've come to the conclusion that this is who you are, don't delay. Because that's my biggest regret. I waited until I was 56 to do this.
I also give myself a little wiggle room there, because I was brought up in a far different time.
I would like to think that people now that are in their teens and early 20s who might be facing some of the same things I was, they are much more empowered now by virtue of society being more accepting and by virtue of there being so much more information available.
I've also learned after making mistakes earlier in my career that if there is unwelcomed news to be shared, the best thing you can do is just get it out there and deal with it. Hoping it goes away almost never helps.
On her daily routine: 'Surround yourself with the best team'
I think getting good rest is always important. And I get up every morning and take a two- to three-mile walk. I also try to read a couple of newspapers in the morning.
I think the other thing that has been really helpful to me, especially in the last five or 10 years, is to surround yourself with the best team. [A team] that you can give them the ball and let them do their own thing.
This interview has been edited for length and clarity.
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This story is part of the Behind the Desk series, where CNBC Make It gets personal with successful business executives to find out everything from how they got to where they are to what makes them get out of bed in the morning to their daily routines.