Podcaster Interviews

Ossa Featured Podcaster: Diann Wingert, Host of The Driven Woman Podcast

Ossa podcaster Diann Wingert is the host of The Driven Woman podcast, a show focusing on helping women entrepreneurs with ADHD traits find success in their endeavors. As a trained therapist, certified coach, and an entrepreneur with ADHD herself, Diann speaks from personal experience, along with years of working with clients, to provides insight into this often overlooked area of entrepreneurship.

All too often, women with ADHD go undiagnosed, creating a negative impact on their productivity, mental health, and overall lifestyle. Diann’s podcast provides expert advice and personal storytelling to amplify empowering perspectives for any entrepreneurial woman struggling with ADHD symptoms.

Read more from Diann Wingert below and listen to The Driven Woman here (leave a review while you’re there, too!).

the driven womanName:

Diann Wingert

Podcast Name:

The Driven Woman

Tell us what your podcast is about in 3 sentences or less! 

The Driven Woman is the go-to podcast for the driven but distracted female entrepreneur who has big, bold goals for her business and life, but needs help to focus, follow through and finish. Many of my audience have ADHD (known or suspected ) and The Driven Woman shares both the skillset and the mindset they need to succeed.

Current hometown: 

Portland, OR. USA

Originally From:

Los Angeles, CA. USA.

What’s a quote or piece of advice that you try to live by? 

Confidence is a choice, not a reward. No amount of achievement makes you confident, you have to decide on it, then develop the skills of maintaining and increasing it.

Ydiann wingertour Superpower:

I’m a wordsmith and ridiculously articulate. I’ve developed it over the years, but its truly a gift I’ve had since childhood.

One thing on your bucket list:

Explore Africa. I have traveled to Asia, Europe and S. America, but still haven’t made it to the African continent.

Personal Anthem:

Fight Song by Rachel Platten

Last Text Message You Sent:

To my daughter Marissa who is struggling in grad school: “Fear doesn’t mean you shouldn’t do it. Fear is just your brain’s response to growth. You can do this.”

What was your first job?

During high school, I worked at Marineland, mainly selling disposable cameras, hats and sunblock to tourists who came to see the killer whale and dolphin shows.

Any unusual hobbies? 

I’m always starting something new, but generally don’t stay with them long term and they are literally all over the place. Some of my past hobbies include: fencing, playing the cello, scuba diving, quilting, collecting Wizard of Oz memorabilia, and jewelry making. As soon as the pandemic is over, I will be signing up for an improv class.

Biggest Pet Peeve? 

People who play the victim. Lots of people have been abused or traumatized. I have empathy for that. But I also believe you can heal and then you owe it to yourself to move on. Playing the victim makes what happened to you an identity and keeps you permanently stuck in the past.

What inspired you to start your podcast? 

My original career goal was to go into broadcasting or journalism, but I allowed a guidance counselor to talk me out of it. Launching a podcast has given me the chance to revisit that dream and do it my way. I love teaching, sharing my perspective and knowing that I am helping people I will never even meet.

Tell us more about your work/life outside of your podcast.

I’m a therapist turned coach, consultant, speaker and writer. I’ve lived in LA my entire life, but in 2019 my husband and I both changed careers and relocated to Portland, OR where we knew no one. When I’m not podcasting, I’m on my Peloton bike, taking classes online (I’m a life-long learner), or exploring the beautiful PNW by hiking or kayaking. I have three grown children who live in CA and hang out with them every Tuesday night on Zoom.

diann wingert

What is your show’s USP?

There are lots of podcasts for female entrepreneurs and a number of shows for adults with ADHD, but my podcast is the only one for female entrepreneurs with ADHD traits. I’m also a trained therapist, a certified coach and an entrepreneur with ADHD, and I’m no beginner.

What is one of the greatest challenges you have personally faced with your podcast?

One of the ways my ADHD affects me is that I can get overwhelmed when there are lots of moving parts or a complicated system. After my first 25 episodes, which were all solo, I wanted to start having guests on my podcast, but I worried that I wouldn’t be able to stay organized, consistent, remember all the follow up involved and be on time and prepared for each interview. Ultimately, I decided to hire a VA to help me because I decided that the show would be better and probably grow faster if I included guests. Of course, managing my perfectionism and forgiving myself when I do mess up is also part of my ongoing process. I don’t just want to have a successful podcast, I also want to enjoy it.

What was one of your favorite episodes you’ve ever done? Why does it stand out?

I have only been podcasting for 8 months and just released episode #37, but one of my favorites so far has been the one I just released. It’s a client success story interview with Nora Wagner, PhD. Her story is really inspiring, it was great to reconnect with her and it was a reminder of not only why I have a podcast but why I quit being a therapist and became a coach. I feel really lucky to work with amazing women like Nora and by sharing her transformation, I hope to touch the lives of other women all over the world.

Listen here:

What is one thing you have accomplished with your podcast thus far that you are most proud of? 

To be honest, it was launching. I had been thinking about it for 2 years. I listened to podcasts, read books, bought the equipment, even hired not one, but two podcast launch coaches but I didn’t pull the trigger. I thought I was planning and preparing the entire time, but I eventually realized that I was procrastinating out of fear and perfectionism. Once I finally faced that and realized I was never going to feel ready, I set a date, entered an accountability challenge and 4 weeks later, my first 3 episodes went live on Apple.

What is one major milestone that you would like to accomplish through your podcast in the next year? 

I am just about to hit the 10k downloads mark, so consistency pays off, but instead of focusing on downloads this year, I want to focus on connection and collaboration. I want to be a guest on 100 podcasts in 2021, or approximately two each week. The Ossa Collective is a perfect place to connect and collaborate with like-minded podcasters!

What is a trend or development in the podcast industry that you foresee happening in the next few years?

I think there will be more independent podcast networks, like the Ossa Collective, that help podcasters grow and monetize their shows and create a sense of community that is so important in preventing podfade. Podcasting is a labor of love and can be lonely, so being part of a collaborative means you don’t have to find sponsors, advertisers and collaboration partners all by yourself.

What is one of the best pieces of podcast-related advice you’ve ever received & why?

Just start. You really don’t have to figure everything out in advance. That was my biggest mistake. You think you know what your show it about, who your audience is, what format you want to use, etc, but you literally have to do it to know for sure. It is truly a learn by doing kind of thing. And, if you’re a perfectionist like I am, you must start before you feel ready. You can’t eliminate the fear of starting by endless preparation, so you might as well just start.

diann wingertWhat is one of the worst pieces of podcast-related advice you’ve ever received & why?

I see countless wannabe podcasters asking questions in FB groups about which title, show art, description, show length, show format, release day, frequency, category, etc is “best” and then acting on the advice of some random person who answers. This is one of the best ways I know to become confused and overwhelmed, which will keep you in the “getting ready” but not launching phase. Unless you have vetted those FB group members and know for a fact that they are your ideal listeners, STOP ASKING for their opinion. I asked a group of dudes at Podcast Movement what they thought of my podcast title and show art. WTF? My podcast is for female entrepreneurs!!!! This is all fear of making a mistake masquerading as market research. You WILL make mistakes. Lots of them. You will feel embarrassed. It’s OK. Keep going anyway. You will figure out it won’t kill you and you’ll learn something.

What are some of your favorite women-hosted podcasts?

Hello Seven with Rachel Rodgers, Savvy Social Podcast with Andrea Jones, The Shine Show with Salome Schillack, The Know, Like & Trust Show with Britany Gardner, Don’t Keep Your Day Job with Cathy Heller, ADHD for Smart Ass Women with Tracy Otsuka

Can you tell us about a time when you took a huge risk/did something you were scared to do, and it totally paid off?

The year I turned 40, I divorced my then husband and became a single parent of three teenagers. I had never owned property in my own name and couldn’t afford a house, but I bought a 2 bedroom condo in a nice neighborhood. My daughter and I had to share a bedroom and we lived there for 5 years while one by one the kids finished high school and left home. I sold that condo for a huge profit and paid for each of my kids to go to college, without taking on student loan debt. I was scared shitless and often dreamed we’d end up living in my car, but that never happened and I am really proud of what a badass I was. I didn’t remarry until ten years later, when all of my kids were grown and flown.

Is there a charity or cause you care about that you would like to share?


How do you feel you’re making a positive impact and generating change through your podcast?

I receive emails, DMs, reviews and shout outs on social media that let me know I’m making a difference.

Stay connected with Diann Wingert and The Driven Woman Podcast:
Website // Instagram // Facebook // LinkedIn

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