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You are here: Home / Blog / Living to Wynn with Maisha Wynn

Living to Wynn with Maisha Wynn

June 1, 2021 by Chi@glance

Maisha Wynn: Author of “The Wynning Way”

Some say she’s a stylist, some say she’s a fitness trainer, some say she’s a nutritionist, and some say she’s a notable book author. If you ask Maisha Wynn to define herself she would say she’s ALL that and much more! Maisha has many talents and she plans on using ALL of them to build her legacy. She has never been a stranger to success. Maisha has worked in advertising and sales. She’s elevated multi-million dollar companies to the next level of stardom. After discovering her passion for helping others she decided to use those skills in her entrepreneurial pursuit of the “Wynning Way.” Maisha is a Lifestyle Specialist that uses her brand to inspire, ignite, and initiate change in others. She speaks her mind and walks in her purpose throughout all facets of her life.

I was super excited to interview Maisha after stumbling across an Instagram post giving her a shout out. It eluded to a TV show she has in the works called “What’s on the menu, Chef.” You know my love of food, so I was immediately intrigued. Maisha has been living a Vegan lifestyle for over five years now. She plans on using her platform to educate others on how to preserve and protect their bodies on the inside and on the outside.

When I called Maisha for our interview I was immediately drawn to her super positive and bubbly personality. She had been up since the wee hours of the morning filming her first International TV segment in Toronto. Her vision of being a powerful international voice to be reckoned with is materialzing just like she knew it would. Want to know her secret? Read our one on one interview below. If you like what you read make sure to pick up a copy of her book, “The Wynning Way: A guide to creating success your way.” For those looking to make an impactful change in your life check out her monthly virtual 14 day reboot program. The practice of self-love is not just a one time event, but an ongoing process. Will talk more about the program in more detail in the interview below. Get ready to Wynn!

Tavi J One on One Interview with Maisha Wynn

One of your philosophies is slow and steady wins the race. Over the last ten years you lost over 120 pounds. You went from a size 20 to a size 4. Can you tell us a little bit about your background and weight-loss journey?

My background is in advertising and sales. I’ve had the pleasure of working with fabulous opulent brands like Salvatore Ferragamo, Mercedes, and Harry Winston (to name a few). I had a real love for people, lifestyle, and just living. When my mother became sick I had a shift in my life and my existence. I received a call from my aunt one day and she said your Mother is having difficulty swallowing and you need to go get her. When I got to the house my mother was slumped over and it was not a pleasant sight. I’m the only child. My mother was my biggest cheerleader, my biggest supporter, and my biggest confidant. She was literally my bestfriend.

My mother would always tell me growing up: Maisha you’re beautiful, you’re great, you’re a leader, and you’re destined for greatness. So that’s how I always lived my life.

To see her slumped over was devastating to my spirit and my soul. I took her to the hospital where the doctor’s discovered she had stage 2 stomach cancer. On the day we were supposed to treat the cancer my mom caught pneumonia and she never came out of it. On Thanksgiving I recall visiting her in the hospital. She wasn’t able to talk or move. She made her transition on New Years Eve.

I tell people all the time you truly don’t know how resilient you are until you’ve reached your lowest point in life. It was in the mist of this darkness where I found my greatest light. I had been making six figures in advertising and then I lost my mom and then I got laid off. I didn’t walk away from my company I actually got laid off the day before Thanksgiving because the company I worked for lost their funding.

I thought back to my Power Boards. What do I mean when I say Power Board? When we put things on paper we’re giving it power. My power boards always have my face in the middle of the board and everything else goes around it because I’m giving power to who I am and where I desire to be in life. I was looking at one of my boards and the board said:

Change
Inspire Lives
You’ll be the next Oprah Winfrey
You’ll be global

God will put us in places where we don’t think we should be, but it was his way of saying this has been something you’ve been praying on and creating these Power Boards for the last few years. It was time to take flight. So I took flight and a month later the company came back and said we have funding again and we’d like to have you back onboard. It was that day I said you know what I’m good. I said that I was good because I had made other people millions of dollars increasing their vision and their brand. It was time for me to give birth to Live to Wynn where we inspire, ignite, and initiate change in others.

My first event was in the South Loop of Chicago. It was the Live to Wynn Lifestyle series. It was my first Lifestyle series event at a small loft and I was charging $50 a person. I’ll never forget someone was like no ones going to pay $50 to come to your event. That’s all I needed. All you need to do is tell me what I can’t do and I’m going to show you what I can do. I had a sold out affair with people standing against the wall.ย  The Lifestyle series grew and I had events at The Park Hyatt, Neiman Marcus, Drake Hotel, and Bloomingdales. Something that had started off so small had manifested into something great. I say all that to say the people that we hang around including family members can either propel us to be who we are truly destined to be or they can bring us down. It’s very important that we are mindful on who we give our energy and our light too. Because they either really increase that flame or burn it out.

When your company had offered you your job back and you responded no… I’m curious what was the final moment or push that you decided I’m going to go the entrepreneurial Lifestyle route?

I had just lost my mom six months earlier and I was thinking, “What is my legacy going to be?” Are people going to say “Oh she worked for such and such”…or do I want my legacy to be “She created her own global brand.” Why global? Because my Mother sent me to Cuba at the age of 11 years old. I speak Japanese, I’ve lived all around the world, and I’m working on my third passport. There was no way I was going to continue working for somebody else when I could create my own legacy. Our legacy is what we do when we are still living. It’s not something we do when we’re 6 feet under. That was my push. It was time for me to create my own legacy versus building up someone else’s.

Let’s go back a minute to the weight lost. If you can tell us how you were able to lose the weight? Also, your journey to a Vegan Lifestyle.

It wasn’t a miracle. A miracle is something that is highly impropable. I’m a living, walking, breathing witness that it is possible. Change is possbile. Change begins first with focusing on your new self versus focusing on your old self. The moment you do that is the moment you become free. That’s why we must be extremely mindful and cogniscent of what we say, what we do, what we think, and what we eat.

Maisha Wynn Before and After Transformation

I was walking by the mirror one day and I looked in the mirror and I said, “Is that me?” I broke down in tears. All the years that people were calling me names it never registered because everyone in my household looked like me. From my mother to my mother’s sister we were all overweight or obese. That day of discovery I called my buddy and I said can you meet me at the gym in my building. He met me at the gym and he showed me around. I never worked out or took a PE class a day in my life. I always had a doctor’s note. I was just lazy.

That day we did a little walking on the treadmill. I always like to say slow and steady wins the race. It is not a sprint, but it’s a slow jog. I slowly started working out once a week and I slowly started taking things out of my lifestyle. That’s where the mental piece comes in. So often you’ll see people lose weight and then gain it back. It’s not because their not working out and it’s not because their eating. It’s because they have not made the commitment to their mental.

Our mind is the greatest gift bestowed to us by our creator and if you desire change it begins with the mind. I said I want to live. I slowly started taking red meat out of my diet and fried food. I loved orange juice, but not the fresh orange juice. The orange juice you buy in the carton with all the sugar. I said okay I’m going to start drinking more water and instead of eating fried chicken I’m going to eat baked chicken. With just those slow changes I started to see a difference in my body. What I have learn is that we have to celebrate every victory. Just drinking a glass of water versus orange juice is something to celebrate. So often we wait for the big monumental celebration, but if we celebrate every small milestone it leads to a larger milestone. We must treat our bodies the same way we treat that new car or those new pairs of stilleto’s or that new hand bag. Just like you cherish material items you need to cherish your body baby. Your body is non- replaceable. Once it breaks down it’s hard to build it back up.

Your book the wynning way is a guide for personal and professional development. Without giving too much away what is the first thing we should do when deciding to make a lifestyle change?ย 

First thing you have to do is really focus and get clear on your WHY. Everything begins with WHY. We have to be extremely intentional with our life. With that comes self reflection. So example…”Why do I desire to lose weight?” “Why is it important for me to lose weight right now.” You want to think about it and then write out at least 3 to 5 reasons on why you need to lose weight. For me it was 1) I don’t want to end down the same road as my beloved Mother, 2) I want to look like the person who I feel like I am inside with my spirit. I want to make sure my spirit matches up with my body. 3) I want to be able to walk up a flight of stairs without being out of breath. Those were some on my Why’s. It’s important that you write it down because seeing is believing and believing is achieving. It’s one thing to know it but it’s another thing when you write it down because once again your giving it power.

You’re a woman of many talents and one of them will be hosting a new show. Can you tell us more about your show “What’s on the menu, Chef” and where we can tune in to watch?

Yes!!! I’m super excited about this. We unveiled the show to the world during black history month as well as Vegan cuisine month. I’ve been Vegan for over 5 years and I became Vegan when I realized I was living with a brain aneurysm. How does it corrleate with being Vegan? Well when my mother was living she was on fifthteen different meds. Four of those meds were for high blood pressure and high blood pressure only elevates ones aneurysm. People don’t understand that the food we eat often times adds inflammation to the body. Inflammation causes other things like cancer, high blood pressure, diabetes, and basically all the things that are really plauging alot of American’s. Espeically women who look like you and I. My primary physican said based upon my family history I really needed to look at a plant based lifestyle. It was the best life decision for me. It changed the way I think to the way that I move. I’m more compassionate and empathetic to myself as well as others. I’m also not on any meds.

“What’s on the menu, Chef” show highlights this lifestyle change. It’s the first of it’s kind travel food show that’s centered around Vegan food, the power of love, and forming human connections. The aim of the show is to offer aspiration and practical guidance for individuals that are looking to live a more abundant and well balanced life which begins on your plate. At the end of the day Chicken or Fish would not be tasty if you took away the seasonings. Am I right? It takes red meat 30 days to digest through the system. Really focus in on your body. On the days that you don’t eat anything except things from the earth, ask your body how it’s feeling versus when you eat chicken, or fish, or beef, or pork. Say body how do I feel now? Your body will tell you everything you need to know. It’s your bestfriend for life.

Awesome! Where can we tune in to see the show?

Right now we’re shopping it around to various networks, but starting this summer we are going to start doing some digital pieces online that you will be able to find on our IG and YouTube @livetowynn.

Where are you going to be filming at?

A lot of places are still shut down. We will be doing things virtually as far as connecting with the Chefs. Once we close our TV deal will be sharing a lot more. Stay connected to us online.

Livetowynn.com
Instagram, Facebook, YouTube – @livetowynn

Last, but not least can you tell us a little bit about your monthly Virtual 14 day Reboot program and how to sign up?

The program starts again on June 21st. Itโ€™s for those who are looking to connect with their inner winner self. How to show ourselves self love, self compassion, and self worth. How can we be good to others unless we are great to ourselves first? For more details and to sign up for the next session clickย HERE.

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Filed Under: Blog, Community/Volunteering, Diary, Entertainment, Events, Health and Beauty, Pampering/Relaxation, Recipe, Restaurants/Dining, Reviews, Spotlight Tagged With: Blog, Community /Volunteering, Diary, Entertainment, Events, Health and Beauty, Pampering/Relaxation, Recipe, Restaurants/dining, Reviews, Spotlight

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2026 ๐“๐จ๐ฉ ๐‚๐ก๐ž๐Ÿ contestant ๐‚๐ก๐ž๐Ÿ ๐Ž๐ฌ๐œ๐š๐ซ ๐ƒ๐ข๐š๐ณ was in Ch 2026 ๐“๐จ๐ฉ ๐‚๐ก๐ž๐Ÿ contestant ๐‚๐ก๐ž๐Ÿ ๐Ž๐ฌ๐œ๐š๐ซ ๐ƒ๐ข๐š๐ณ was in Chicago for an intimate VIP media dinner hosted by @VisitNC. Chef Diaz is based in Durham, North Carolina and has multiple restaurants, ๐๐”๐“ he was born in raised right here in Chicago. He might have even shared that if he has it his way he seeโ€™s a future restaurant venture in the Chicago Logan Square neighborhood. How lucky would we all be!

The evenings menu was FANTASTIC from the mole to the best green beans Iโ€™ve ever had.  AND ofcourse I asked him about his time on Top Chef. He had 3 words. ๐Ÿ˜‰ Thanks for a lovely dinner @Buenosdiaz ๐Ÿ˜‹ I hope to make it to North Carolina soon! 

#Visitnc #Topchef #Chicagoevents #Chicagofoodie #Northcarolinafoodie
I was invited to attend the ๐Ž๐›๐š๐ฆ๐š ๐๐ซ๐ž๐ฌ๐ข๐๐ž๐ง๐ญ๐ข๐š๐ฅ ๐‚๐ž๐ง I was invited to attend the ๐Ž๐›๐š๐ฆ๐š ๐๐ซ๐ž๐ฌ๐ข๐๐ž๐ง๐ญ๐ข๐š๐ฅ ๐‚๐ž๐ง๐ญ๐ž๐ซ Press Preview Day, June 3rd. What an honor to be in the building ahead of the June 19th public opening. 

We gathered in the auditorium of the Forum Building to hear a briefing from ๐—ฉ๐—ฎ๐—น๐—ฒ๐—ฟ๐—ถ๐—ฒ ๐—๐—ฎ๐—ฟ๐—ฟ๐—ฒ๐˜๐˜, ๐—–๐—˜๐—ข ๐—ผ๐—ณ ๐˜๐—ต๐—ฒ ๐—ข๐—ฏ๐—ฎ๐—บ๐—ฎ ๐—™๐—ผ๐˜‚๐—ป๐—ฑ๐—ฎ๐˜๐—ถ๐—ผ๐—ป. We also took an intimate stroll through the museum with subject matter experts stationed throughout to help answer any questions. This experience was AMAZING! I interviewed ๐—๐—ผ๐—ต๐—ป ๐—ฅ๐—ผ๐—ฏ๐—ฒ๐—ฟ๐˜€๐—ผ๐—ป. He serves as incoming Executive Vice President of the Obama Presidential Center. In his role he oversees the Centerโ€™s operations as they prepare for the public opening, June 19th. (Full interview on @chiataglance YouTube channel)

Thereโ€™s so many FREE public activities during the Grand Opening which is June 19th - 21st. Iโ€™m sharing them with you on the blog (Link in Bio). Do you have your tickets?๐ŸŽŸ๏ธ @obamafoundation 

#ObamaPresidentialCenter #Chicago #Obamafoundation #Chicagohistory #Chicagoevents
Sunday Funday with @theblackfoodies + @Domuchicago Sunday Funday with @theblackfoodies + @Domuchicago Apartments. Luxury Bus ๐“๐š๐ฌ๐ญ๐ž ๐š๐ง๐ ๐“๐จ๐ฎ๐ซ ๐‚๐ก๐ข๐œ๐š๐ ๐จ in session. ๐Ÿ˜‹

@Pizanospizzachi

@Rickettes_world_famous 

@Bronzevillehoagiepanini

@Kilwinschicago

@Wilmasfamousbbqandtavern

@Poparazzispopcorn

@Pollyanncakes

Eating our way through Chicago while stopping at iconic/historic landmarks. Thanks for the ride! ๐ŸšŒ 

#Chicago #Chicagorestaurants #chicagofoodie #Chicagofood chicagoevents
Memorial Day weekend is coming up and what better Memorial Day weekend is coming up and what better way to kick off summer thanโ€ฆ on a BOAT! Yesterday I joined Chicago Line Cruises on their signature architecture river tour. We did a 90 minute cruise down the river as our expert guide discussed the history, impact, and legacy of Chicagoโ€™s renowned architecture. ๐‘จ๐‘ต๐‘ซ on Thursdays theyโ€™ll be hosting wine and whisky tastings. Congrats to 40 years on the historic Ogden Strip! Get your tickets TODAY!
@chicagolinecruises ๐Ÿ“465 N McClurg Court

#Chicago #chicagotastings #architecture #chicagoboating #chicagoarchitecturetour
I slept in a treehouse last night and what an adve I slept in a treehouse last night and what an adventure! @Kalahariresortswisconsindells unveiled a collection of luxury Treehouses created in partnership with Pete Nelson of @NelsonTreehouse, widely known as the host of Animal Planetโ€™s ๐‘ป๐’“๐’†๐’†๐’‰๐’๐’–๐’”๐’† ๐‘ด๐’‚๐’”๐’•๐’†๐’“๐’”. 

I attended an intimate media preview. Pete Nelson and Todd Nelson, founder of @Kalahariresorts, shared the inspiration, craftsmanship, and vision behind the Treehouses on our guided tour. The treehouses provide an elevated escape. Theyโ€™re a nature-forward expansion celebrating the beauty of the Dells and the magic of living among the trees. Also onsite is a relaxing pool and hot tub.

The evening concluded with a beautiful experience on the shores of Lake Delton. We had an amazing dinner at the brand New restaurant @Daylenessupperclub. Such cozy vibes, delicious food, and tasty cocktails. ๐™„๐™ฉโ€™๐™จ ๐™ฉ๐™ž๐™ข๐™š ๐™ฉ๐™ค ๐™ฅ๐™ก๐™–๐™ฃ ๐™”๐™Š๐™๐™ ๐™ฉ๐™ง๐™š๐™š๐™๐™ค๐™ช๐™จ๐™š ๐™จ๐™ฉ๐™–๐™ฎ!

#Kalahariresorts #treehousemasters #Wisconsindells #lovekalahari #TravelWI
The National Restaurant Association Show is going The National Restaurant Association Show is going on NOW! (May 16th - 19th). Iโ€™ve been going since 2018 and this is one of my favorite shows to cover. The NRA show brings professionals from across the globe to discover innovations, build connections, and drive the industry forward. 

@nationalrestaurantshow has 53,000+ attendees, 2,300+ exhibitors, and features 900+ categories. 

๐‘พ๐’‰๐’‚๐’• ๐’…๐’Š๐’… ๐‘ฐ ๐’ˆ๐’†๐’• ๐’Š๐’๐’•๐’ ๐’•๐’‰๐’Š๐’” ๐’š๐’†๐’‚๐’“ ๐’”๐’ ๐’‡๐’‚๐’“?

โœ… Walked the show room floor to discover new innovative technology gadgets. 

โœ… Culinary demo and tasting with celebrity chef @chefchriscosentino. (Winner of Top Chef Masters).

โœ… Each year love picking up my personalized bottle of ketchup from @Heinz.

โœ… Walking the show room floor for tasty bites from companies like @Hormelfoods. That spam dog! ๐Ÿ˜‹ AND the Brisket grilled cheeses from @jtm_food_service And the refreshing tonics from @drinktractor 

#2026RestaurantShow #Chicago #Keynote #celebritychef #chicagorestaurants
Last night I kicked off the National Restaurant As Last night I kicked off the National Restaurant Association show by attending the @Menumastersawards ceremony. The 29th annual celebration is the restaurants industry premier recognition of menu innovation excellence. The event is by invitation only and for restaurant executives. Congrats to the Hall of Fame winner Chef @grant_achatz.  The competition recognizes R&D leaders for their groundbreaking achievements and lasting contributions to food service.

The event offered a one-night-only culinary experience. The tasting menu was crafted exclusively for this celebration.

The after party presented by @Ventura_Foods is not to be missed. We were treated to high energy entertainment, music, dancing, snacks, desserts, cocktails, AND a special gift! We each got a signed autographed copy of ๐—–๐—ต๐—ฒ๐—ณ ๐—š๐—ฟ๐—ฎ๐—ป๐˜ ๐—”๐—ฐ๐—ต๐—ฎ๐˜๐˜‡ book, ๐˜“๐˜ช๐˜ง๐˜ฆ ๐˜ฐ๐˜ฏ ๐˜ต๐˜ฉ๐˜ฆ ๐˜“๐˜ช๐˜ฏ๐˜ฆ. What a fun evening! #MenuMasters

#2026Restaurantshow #chefgrantachatz #chicagorestaurants #foodblogger
YOU deserve a staycation! I headed about 30 miles YOU deserve a staycation! I headed about 30 miles outside downtown Chicago to ๐–๐ข๐ง๐ ๐‚๐ซ๐ž๐ž๐ค ๐‚๐ก๐ข๐œ๐š๐ ๐จ ๐’๐จ๐ฎ๐ญ๐ก๐ฅ๐š๐ง๐. @Wcsouthland is a luxurious escape from the city. The state of the art hotel opened in 2025 and has over 255 rooms and 43+ suites. Thereโ€™s a pool, fitness center, and a full service luxury spa @wcsouthlandspa that spans 11,665 square feet. The 70,000 square foot casino offers 1,412 slot machines, 56 table games, poker room, and the newly opened - Sportsbook. Sportsbook is a high energy, 24/7 destination for sports fans to watch and wager. 

As a foodie my FAVORITE part is well the FOOD. ๐Ÿ˜† I loved my dinner at Chef @Fabioviviani restaurant @altosteakhouse. We also enjoyed the Food Bazaar located on the ground floor. Thereโ€™s six restaurants within the food bazaar and theyโ€™re all you can eat. I highly recommend heading to Chicago Southland for a staycation @wcsouthland.
๐Ÿ“17300 S Halsted St, East Hazel Crest, IL

#Findyourwinningmoment #Chicagofoodie #chicagohotel #chicagostaycation #chicago @Visitsouthland ๐Ÿ‘ˆ๐Ÿฝ
I had one of the BEST spa experiences at Wind Cree I had one of the BEST spa experiences at Wind Creek Southland Spa. ๐Ÿ˜Œ

@Wcsouthlandspa is 11,000+ square feet and overlooks the Chicago skyline. The peaceful retreat is guided by a deep commitment to holistic wellness and relaxation. I started off in the heated jacuzzi whirl pool and then had a a rejuvenating facial. My skin was glowing immediately! My friend decided to do a cupping massage for the first time and she could feel the detoxification running through her body. 

Afterwards we both enjoyed the sauna and relaxed with some refreshing fruit infused water while overlooking the skyline. It was the perfect Sunday Funday. Check them out! ๐Ÿ“17300 S Halsted St, Hazel Crest, IL located inside @Wcsouthland

#FindYourWinningMoment #chicagospa #Chicagosouthland #Chicagostaycation #Chicagohotel @visitsouthland
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