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What does it really mean to choose yourself—and build a business from it? In this candid episode of the Convene podcast, DeShawn Wynn shares her path to entrepreneurship, how she developed a "winning mindset," and why success requires internal clarity, external support, and the courage to pivot.
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Convene Series: How Choosing Yourself Can Lead to a Thriving Business: Lessons from DeShawn Wynn
*Note: the transcript is AI generated, excuse typos and inaccuracies
DeShawn Wynn: I can go outside of the box and I can create the life that I really want to create. And so that's what choosing yourself is.
Magdalina Atanassova: This is the Convene podcast. What does it really mean to choose yourself—and how do you build a business from that decision?
In this season 7 episode, we’re joined by DeShawn Wynn, Chief Meeting Architect at Wynning Touch Event Design. DeShawn began her entrepreneurial journey in the third grade and has since built a thriving career by embracing risk, trusting her vision, and cultivating what she calls a “wynning” mindset.
She shares how mindset impacts leadership, how to build a profitable business with purpose, and why saying no can be just as powerful as saying yes. Tune in for real talk on fear, failure, freedom—and the lessons behind building a business on your own terms.
We start now.
Many event professionals hesitate to take the leap to starting out on their own.
What does it really mean to choose yourself, and how did you make that decision in your own career?
DeShawn Wynn: I think choosing yourself is really going after what it is that you truly desire.
I always joke about the fact that I have realized that I do not make a good employee.
So whenever I was working for someone else, it just didn't feel right. I didn't like it.
I really believe that I was born a natural entrepreneur. I started my first business in the third grade.
My mind thinks like an entrepreneur. And I think that a lot of times we try to fit that square peg in a round hole because someone told us that this is the way you're supposed to go through life.
And choosing yourself is just saying,
I don't have to fit that,
you know, that blueprint, or I don't have to fit that idea. Like, I can go outside of the box and I can create the life that I really want to create.
And so that's what choosing yourself is. So was it easy? No,
it took me a while. It took me a while. A long time of being frustrated.
But, yeah, I say that this has been the hardest thing that I've ever done,
but also the most rewarding, most fulfilling, and I would do it again in a heartbeat.
Magdalina Atanassova: I bet it's a scary feeling. I understand the frustration,
and I'm sure that many people have that frustration. But then it passes, right? You just have a hard moment and then it passes.
DeShawn Wynn: No, no,
you have lots of hard moments.
But I think what does happen is you get better at getting through them. So I remember when I went to file my paperwork and get my business name and I was all excited and I filled out the paperwork and then I got into the elevator.
And as I was going down the elevator, I was like, oh, we really about to do this.
And then it's like, you know, panic struck and, you know, sweat starts going down your face. But it was, it was like, it became very real. Like, I'm really about to do this.
And so, you know, then you go into the hurdles of,
you know, I come from. What's interesting is I come from a family of entrepreneurs. However,
they are not traditional in the sense of they ran their businesses while working full time.
So, you know, every,
everybody in my, my sister, my brother, father, they all had side gigs that were 100% their own, but they worked a full time job. And so when it comes to me who is like, forget the full time job, I'm just going to do the entrepreneurial thing.
You know, my mom was just like, what do you have against working? Like, you know,
she did not understand it. And so, you know, it becomes that where it' I say sometimes entrepreneurship can also be a very lonely time because nobody understands the reason why you have this drive or the reason, you know, and it's like, when you go through that struggle, it's like,
you know, oh, we have a slump in sales. You know, people are just like, well, go get a job. Like, why are you, why are you stressing out? Why are you struggling?
And it's this time where you're constantly trying to explain like, no, this is my vision, this is my goal, this is what I want to go after. And a lot of times people don't understand it.
I remember advice that my aunt gave me when I first started my business, and she was like, no, she's like, you know, get a good county job, you know, work for 20 years, collect your pension, and then start your business.
I'm just like, I,
I want to be vacationing.
Like, I don't want to be starting a business after 20 years of working. Like, I want to be able to reap the rewards after 20 years of working. So it's, you know, it's a constant,
It's a constant challenge because, you know, something new is always going to come up. You know, the, we had the pandemic. So, you know, that's a totally different shift. You know, how, how does my business model need to change?
How do I need to pivot in order to stay viable? You know, the, the economy's going up, you know, you got the, you know, prices going up, you know, and it's like, how do I maneuver these things?
And, you know, how do I be the best for My clients and how do I be the best for me? Like, I don't think there's ever a point where you don't have a challenge or it's just smooth selling.
You just learn to lean into it and keep going.
Magdalina Atanassova: I love that.
And I've read that in some of the descriptions about you about cultivating a winning mindset. And I love how winning is written piggybacking off of your surname, Wy.
And I love it.
What are the characteristics of, of a winning mindset?
DeShawn Wynn: It's really paying attention to the messages that you're giving yourself.
Because a lot of times we're having conversations with ourselves, you know, all day, every day, but a lot of times we don't pay attention to what it is that we're telling ourselves.
And sometimes the messages that we're giving ourselves are counter to our goals and where we want to go. And so the winning mindset is really just taking the time to sit down and figure out, you know, what is it that I'm truly believing?
Like, what is it that I'm truly working towards? And,
and am I feeding myself that message that's going to get me to where I want to go? And, you know, just making sure that you're not,
you know, you're, you're not telling yourself things that are going to hinder you. Like, you're, you know, that, that you're not, if you're trying to grow a successful business, that you're not feeding yourself a message of, I can't do this, and it may not come out of your mouth,
but there are going to be things that you know in your heart and in your mind where that's really your belief. And unless you really, you know, focus, sit down, figure out what is it that I'm thinking, you know, what is it that's in my subconscious?
Like, reaching those goals are going to be very difficult, if not impossible.
Yeah.
Magdalina Atanassova: So because you battle all those internal fears, Right?
DeShawn Wynn: And yes,
and a lot of times it's, you know, it's coming from past trauma. A lot of times it's coming from the messages that you're hearing from other people, you know, because if the messages that you're hearing from other people is, you know, oh, you need to go get a 9 to 5,
you know, in this entrepreneurship thing is not going to work, you know, are you really internalizing that? Are you believing it? Or are you really saying, you know, no, this is going to work?
Like, what are you internalizing and how is that affecting you, reaching your goal? And you Know also, you know, what. What trauma or what lesson or what past experience have you stuffed down?
But it's still, you know, resurfacing and, you know, subconscious ways.
Magdalina Atanassova: Any advice you can give on how to go about it, of course it will be personal. There will be things not everyone can apply. But how did you go about really taking.
DeShawn Wynn: Really taking the time to think about what? I think about doing a lot of journaling, doing a lot of just analyzing. Why am I stuck? Like, what, you know, what is it about, you know, what is it that's scaring me?
You know, what is it? Why can't I get over this hurdle? And then once I figure out, okay, this is what's scaring me? Why is it scaring me? Like, you know, what.
What happened that got me to this point? You know, what. What lie am I believing about this moment? And then, you know, journaling it out,
talking with other people,
you know, just about, hey, this is what I'm struggling with. Because a lot of times other people can see you better than you can see yourself.
So having those conversations with trusted friends,
trusted people, or, you know, getting therapy, but just really taking the time to sit down and listen to yourself.
Magdalina Atanassova: I love that. Especially when all these negative messages come sometimes from your closest people and they are actually trying to protect you, not being, you know, disappointed or ending up, you know, without being financially secure.
DeShawn Wynn: Right.
Magdalina Atanassova: So it's really hard to navigate and not at least a little bit listen to them, because, yeah, you're also afraid of all these things happening to you.
DeShawn Wynn: Right? Exactly. Exactly. And you do gain momentum because, you know, when you realize what it is that you're afraid of and you realize, you know, what it is, what your triggers are, you know, and.
And then you have that win then, because then you have something to build on and be like, no, you know, I've been through this before. Like, I came out on the other side.
And so you can build on that momentum, but if you're always living in a. In a doomsday scenario,
then you're going to lead into that. And, I mean, I think that one of the things, like, I have had to pretty much turn off the news because I think the news keeps you in a doomsday scenario where everything is always going to go wrong.
The time, you know, so you just. It's. It's also what you feed yourself. So I'm a person. I listen to a lot of podcasts that are going to be, you know, positive mindset podcast.
I'm, I'm, you know, limiting the Amount of news and the, and then sensationalized gossip. And you know, I'm turning that off because it also, you know, is very important what you're feeding yourself.
And then the people who I'm surrounding myself with, I'm surrounding myself with people who are in the places that I want to be. So you know, picking your friends wisely and then distancing yourselves from the people who are not, who are not going to help you get to where you are.
So you know, if you're, if you're constantly surrounding yourself with people who are telling you that you're not going to make it, you know, you're going to lean into that.
So surrounding yourself with people who are making it and have that same,
that same desire, vision and drive that you have, it definitely helps, you know, the use of mastermind groups and you know, like minded people who can hold you accountable and who want to see you win.
Those are definitely ways that you know, can move you forward.
Magdalina Atanassova: And let's say our listeners, or at least one of our listeners is taking that leap.
How can, like, what are the steps they should take to build a profitable business? Any suggestions that you can give them?
DeShawn Wynn: Again, I think it goes to being laser focused and really taking the time to sit down and decide what is it that I want,
where do I want this business to go? Creating that vision and locking that vision in.
And then when you see that vision helping, you know, going and getting help to make sure that you know, you are able to give the best service that you can give.
So you know, what skills do I need to learn? You know, how am I going to be the best at what this is that I'm giving and making sure that you seek that help to get those skills up.
And then again,
locking in as far as building a network,
getting the resources and then continually evaluating and moving,
not being tied to this is the only way that this goal can happen. But being flexible enough that as roadblocks or pivots come,
you're okay with pivoting because you're constantly asking yourself this question of how does this get me to my goal?
And if you're stuck in this, this is the only way it can happen.
You may delay or even block what's really truly for you. So saying this is the goal, but how I'm getting there,
it might turn, it might move, it might pivot, and I'm okay with that. I'm just going to follow the journey and I'm not going to be, you're going to get nervous, you're going to be scared, but I'm going to go with it and I'm going to enjoy the journey.
Magdalina Atanassova: What are some misconceptions that people may have about entrepreneurship in the industry and what's really behind them?
DeShawn Wynn: I think that a lot of times we have done this disservice of meeting planners, our superheroes.
Meeting planners are invincible. And I think with social media, with us having Zoom and all of this technology,
people now think that they have access to you 24 hours a day, seven days a week. And whenever I want you, I need you to be responsive. And I think a lot of times, especially as entrepreneurs, we take on that burden of I always have to be on, like,
what do they need?
And it's very easy to forget about yourself and just focus totally on the business and, you know, and not take those moments of breaks and, you know, working crazy hours and, you know,
not giving yourself time to just shut it off and shut it down. And yes, there are going to be times where, you know, you're going to have to give it a little bit more.
You're going to have to do those late nights, early mornings. But it should not be every week. It should not be every day. Like, it should not be a constant.
One of the best things that ever happened to me is somebody hacked my email about two years ago. And so what was happening was they had sent out these robo emails.
And so I was getting all the bounce backs, and so it was coming up on my phone. And so, like, every three seconds I was getting this, you know, 200 emails, 200 bounce backs that were coming to my phone.
And it was driving me crazy because it was, like, immediately putting me in that. Who's emailing me, what's happening, you know, that type of thing that. That anxiety. And so I had to remove my email notifications from my phone.
It was the best thing I've ever done. And I have not put them back because.
Because I'm not getting that constant, you know, that constant ping of, you know, do I need. What do I need to do? You know, I was waking up in the morning and the first thing that I was doing was picking up my phone to see who.
Who emailed me, you know, what do I need to go. And that is such a wrong way to start your day.
So, yes, now it's like, no, this is, you know, figuring out how is it that I want to start my day. And again, choosing me. Like, I own this business.
I tell people how to treat me,
and this is. This is the life that I Want to live. This is how I want to start my mornings. Not in a panicked,
you know, running to my computer.
For sure.
Magdalina Atanassova: I was wondering where you're going to go with, they hacked my email. And that was the best thing that ever happened to me.
It doesn't sound like it, but I see your point.
Well, I hope people don't wait for the email to be hacked to stop their notifications.
DeShawn Wynn: Right, exactly, exactly. Like, do it now before start the robo. The robo bounce back.
Magdalina Atanassova: And how has your leadership style evolved because of that journey that you're on?
DeShawn Wynn: It's a matter of trust. I'm learning to trust. I think when I first started my business, it was like, this is my baby.
I can't give out anything for my baby. Like, I got to do it all. And so now I'm at a place where I can't do it all. I don't want to do it all again.
I'm choosing the life that I want and choosing how I want to spend my day. And based on that vision for my life, I need help. So I need people to help me.
And so allowing. Trusting people to help me one and then trusting them to do what it is that they were brought in to do.
So, you know,
staying in my lane,
understanding my lane. That's your lane. This is my lane. I'm gonna stay out of it. And so it's. It's really been, again, a journey of me just learning how to trust.
And then when. Because again, we go back to talking about how,
you know, the fear never goes away, you just learn how to handle it more because there will be times when, you know people are going to fail you or people are not going to do what they say that they're going to do.
And, you know,
that could turn you back into the spiral of, see, I knew I can't trust nobody. I got to do it all myself,
you know,
so again, not allowing that to dictate how you move, you know, just, hey, bumps in the road come. That wasn't the person for you. Let's. Let's find the person who, you know, can do what it is that you need them to do.
And rolling into that and not.
And not being triggered. Still working on that.
But, yeah, it's getting better. Getting better.
Magdalina Atanassova: I have to plug in here that corporate jobs also make you feel that way where, you know, when people fail you and then you're like, oh, I should do it all myself, and you end up in that same loop.
And the other thing, I don't think many Let me backtrack. I don't know how many people realize that actually being an entrepreneur, you rely a lot on other people. It's not.
You're braving, you know, the wilderness. I feel like I'm quoting Brene Brown's book. But, you know,
you're not.
You don't have to do it all on your own. You're not. You are conquering your fears.
That's your own thing. But then everything else, you can lean on people and use their help, right?
DeShawn Wynn: I mean, that's the key to success. Because if you're not, then it's going to be extremely hard for you to be successful. Just because it's.
It's just. It's too much is not. It's not possible.
I also think that it's. It's critical to.
It goes to that what I was saying in terms of being able to pivot quickly because again, you know, if you put somebody in this position to help you and they're not helping you, you know,
being able to cut it off and move on in a timely manner and not dragging it out and therefore setting yourself back. So again, being able to be like, oh, this was not the move.
Let's find the correct move and being. And doing it quickly, I think that's the other key.
Magdalina Atanassova: Do you remember such a moment that you can highlight?
DeShawn Wynn: I think when I first started my business,
I had an amazing. Had amazing contract.
I was doing two to three community meetings a week.
Money was flowing. It was great.
And what happened with me is I was so focused on that job, that client,
and I wasn't continuing to prepare in case that went away.
And so, and so I still wasn't out there prospecting,
you know, I was no longer, you know, networking. I was locked into this contract and it was. This is what my focus. And, you know,
I'm locked into this. And then the contract went away because funding went away.
And then I'm sitting there and I'm like, what I do now?
So I basically had to start at ground zero because it was not a subtle, like, we'll give you three months. It was like, no, it's over. Money stopped. And so again, it was a lesson for me in terms of not,
you know, never getting so comfortable, you know, with the contract or. Or with a client that I think that it. It's that I'm not considering what else can come along or not considering, you know, what's going to happen after this and not considering other ways, you know, because who knows what business that I overlooked because I was so locked into this one contract and so really getting in the mindset of just being open to.
You never know what's going to come your way. And being open to looking at the big picture and at your surrounding environment and not just looking at the small thing that's in front of you.
Magdalina Atanassova: And you mentioned networking. In our industry, everything's relationship based. So how do you keep up with that?
DeShawn Wynn: I'm intentional with my networking.
I look at things that I need,
that I need strength in, and I look for that in my networking. So when I first started my business, I didn't. I needed help with, you know, I don't know how much I should be charging.
I don't know how I should set myself up. And so, you know, I looked at people in the industry who were where I wanted to be and I called them up and I'm like, hey, can we have lunch?
You know, let's talk. And I started building my network there. You know, I have a dear friend who's in Baltimore, Kareem Swinton. And I will never forget. I walked up to him, he was in sales and I walked up to him, I was like, I need to learn how to sell.
I need to learn how to look at these contracts. You're going to help me.
Magdalina Atanassova: Okay.
DeShawn Wynn: He really helped me build my career because, you know, I was able to pick up the phone and call him, like, what do I do? How do I do? And so, you know,
a lot of times we talk about, you know, joining these organizations, like joining a PCMA, but yes, join the PCMA, but while you're in PCMA, like, take a look at who's there, take a look at who's around and, and start using that to,
to, you know, find out the things that you need to know to be successful.
Magdalina Atanassova: Yeah,
definitely. I love that approach. Also. Just pick up the phone,
you know, shoot that message and ask for help.
Actually, people are very open because we all love to be needed, so.
DeShawn Wynn: Exactly,
exactly. I mean, and people aren't used to being asked. And so it's like, you know, when somebody actually sits down and asks you, it's like, oh, okay,
yeah.
Magdalina Atanassova: What would be the one piece of advice you wish you had when you were starting? Winning Touch Event design.
DeShawn Wynn: All money is not good money.
Choosing wisely again, you know, as entrepreneurs, especially when I started, it was like, if, if, if somebody asked me, I was going to take it. Yes, yes, take the money, Take the money.
You know, and, and again, that was based out of fear.
But really looking at where is it that I want to go.
And when the contract or the opportunity comes along,
really evaluating, is this going to get me closer to where I want to go, or is it going to hold me back and trusting myself, my skills and my knowledge enough to not take everything or take, you know, jobs out of fear, but really going after and choosing things that are going to get me to the next level of where I want to be?
Magdalina Atanassova: Very nice. Was there anything we didn't mention we should before we end?
DeShawn Wynn: Oh, wow. We talked about a lot. I guess the other thing that people, a lot of times people say, you know, oh, you know, I want to own my own business.
But one thing that I have also realized as, you know, being 15 years owning my own business, not everybody was made to be an entrepreneur. And that's okay.
Really sit down and figure out before you take that leap if this is really who you're built to be, you know, because it's a struggle, you know, you're constantly, you know, having to prospect.
You're looking, you know, your. Your ability to take no for an answer. You know, how do you respond when.
When things don't go your way? Like, are you more comfortable with the security of a 9 to 5,
knowing that, you know, your check is guaranteed? Well, somewhat guaranteed. You still can get fired, but, you know, you have that security and it's okay if that's who you need to be.
You know, some people like myself, I just,
I like the freedom more than I like the security.
And, and that's, you know, just really knowing and understanding who you are and standing firm in that.
Magdalina Atanassova: Very nice end to our conversation, thank you, DeShawn, so much for making the time and sharing your lessons learned on this journey.
DeShawn Wynn: Thank you.
Magdalina Atanassova: Remember to subscribe to the Convene Podcast on your favorite listening platform to stay updated with our latest episodes. For further industry insights from the Convene team, head over to PCMA.org/convene. My name is Maggie. Stay inspired. Keep inspiring. And until next time.