Sadie Shepard is so, refreshingly real. I noticed it immediately the first time I spoke to her, which was on the phone, late last year. I had connected with her because we were part of the same women’s group, and instantaneously I felt like I could share my own challenges and struggles, despite barely knowing her.
While most people fear sharing anything but positive updates, Sadie isn’t scared to discuss the difficult things she has experienced — which is extraordinarily rare, especially without veering into the opposite end of oversharing.
Sadie worked in tech, SaaS, and real estate for ten years before starting her own coaching firm. She uses her experience as a business leader and growth strategist to carry out her ultimate mission: helping female founders transform their ventures from successful to scalable.
Today, she is sharing the ups and downs of her life story: from being an unexpected caregiver in her twenties, to getting laid off when she was soaring in her career, to learning to manage her ADHD diagnosis as a business owner. I hope you enjoy the conversation and that you also pick up on some of her energy that helps us all feel more comfortable with…being ourselves.
You’ve had such a unique journey. Where do you want to start?
One thing I've thought about a lot in adulthood — that I don't think I could label when growing up — is that I often felt like I did not “fit in,” despite having several friends, hobbies, and interests.
Once I was diagnosed with ADHD, I was like, oh, this makes sense. Especially now as an adult.
I've gotten to a point where I can appreciate much of what comes with having ADHD, but for a long time, it was an overwhelming challenge.
I’ve struggled with the stick-to-itiveness of following through with things I'm not interested in since as long as I can remember. I would be all-in on theater one semester, then I’d be trying out for the lacrosse team the next. I transferred high schools, I transferred colleges. I changed my major a handful of times. For better or for worse, I've never been risk-adverse. Seeking out new experiences has always been in my DNA.
When were you diagnosed?
I was diagnosed when I was 16. But you could see the signs early on, even in class.
For example, once we got to the fifth grade, you would go to different teachers' rooms for different subjects. And I was the last person to leave the class, every single time. And I didn't understand why kids around me could easily shift into the next gear. But for me, it was really hard for me to context switch, and to literally gather all my things and pack all my stuff.
The way that my brain thinks about categorizing, segmenting, and even just organizing concepts, ideas, and physical things has always been very different from people around me.
Can you share any examples of that?
A great example is my organized, messy workspace. So what I mean by that is: I could have shit everywhere, but it’s going to be tidy with a mental catalog as to why I need to put that with this. My systems make perfect sense to me, but to others, it can be like, wait, take a few steps back — I’m not following.
I had to try really freaking hard to operate at what seemed so baseline to everybody around me. It was like I felt everything all the time, all at once, really loud, and I just didn't even know what to do with it — like there were filters everybody else had that I didn't.
But in one way that it’s served me — I've always been somebody who is absolutely, all-in on whatever I'm passionate about.
Do you see your ADHD as an asset now?
Yes. I can find themes, and connect things in a way that is just second nature.
I have a hard time explaining to people sometimes when they ask, how did you come to this conclusion? The dots just seem so obvious to me. One gift with ADHD is being able to see all the little nuances and things that play together and influence each other.
I could talk your ear off all day about just this. It's fascinating the amount that I've learned about this, just in the last few years.
Ooh, like what?
Well, for starters, the spectrum is just insane. For example, my husband also has ADHD, but he is completely the opposite in the way that it manifests.
I have to recharge by doing nothing. It’s spooky probably to some people —I can just sit and zone out. But that's actually just me processing and decompressing in real time. My husband is very opposite, in that he processes a lot of things by going and going.
I’ve seen you discuss ADHD in your social media posts, as a business owner. What is it like sharing that in public?
I think that, like most things, not talking about it is a disadvantage for other people to learn from you. The reason I am an open book about this, and really all things, is I always want to create a safe space for those past versions of myself.
The people that I work with really appreciate the fact that I have the realness because it gives them the space to show up as their whole selves, too. For business owners, your work and self are so connected. Why would I ever expect someone to show up as his or her full self if I'm hiding parts of myself?
Can you talk more about the other setbacks that have shaped you?
Yeah. First there was my dad’s spinal cord injury in 2018. The doctors told us he wouldn’t walk again.
I moved back home to Kansas City from Denver, which in its own right was so hard because I'd proudly built this life for myself out there. My mom turned into a caregiver overnight.
My dad, though, is a seriously stubborn person. He told himself he was going to walk his girls down the aisle one day. And so he really made it his ambition to be able to regain some of his independence.
Meanwhile, I also lost a close friend to gun violence. It was a really traumatic, terrible situation.
I wanted to lean on my friends for support, given what was going on with my family, but they were processing their own grief, too.
That's interesting too, because sometimes we forget how difficult it is when someone else in our life is facing a setback. In this case, it was your dad, and your close friends. So you can't just lean on them the same way you normally would, because they’re going through a hard time, too.
I kept thinking, is anything else gonna drop?
So now it’s 2020, you’re working at WeWork, and you go through a layoff. How did you deal with that?
I was upset, but I was also sad for just the whole situation. In January, I had blown out my sales numbers, and I had had this company-wide recognition. Then in February, I left. And then COVID happened. I felt like I could not get a break.
I got my real estate license, then ended up getting another job, before launching my own business.
Your consulting firm is specifically for female business owners. Why did you choose to do that?
In my career, I was often working with men twice my age who didn't respect or value my opinions and expertise. I was desperate for a female ally — someone to pull me up the way I was trying to advocate for myself.
However, I’ve also seen the positive impact workplace culture can have, too. For example, I couldn’t imagine going through the experience with my dad without the kind of support, trust, and value my employer at the time had in me.
But over time, working at companies of different stages and sizes and industries, I learned the system was not designed for me. I’ve seen that women get shit done and have a lot of great ideas. But we don't have as much opportunity in these spaces to have influence.
Rather than continue trying to fit into a framework that undervalued my contributions, I decided to make my own.
My dad told me as a child that the safest bet I would ever make was betting on myself as a business owner. That stayed with me.
But I would say it took me every bit of three years to really get serious about the fact that I could start my own business.
What are the themes you see in working with your clients?
Most of the playbooks for things in business — the top sales books, how to create a minimum viable product, how to negotiate — they’re written by men. I've read, consumed a lot of them. While they’re valuable, they're not written from the female perspective. People often say, go read books to educate yourselves. But sometimes it’s harder to actually apply those lessons because our shared experiences are so different.
Also, women business owners can be quick to invalidate some of their successes or their wins. They say, I got help from others, so I can’t celebrate. What is really rewarding in my business is to remind women to pause and celebrate their own achievements.
I want women to feel there's someone in their corner. Who can teach them to do things not just in the “standard” way, but a way that’s aligned to them and their experiences as a woman.
If you were to give advice to someone who's going through a lot of challenges right now, what would you say?
Let other people show up for you and know that people will. Their intentions are probably good, even if their delivery is wrong. The other thing is asking for what you need. I know that there were times that I felt resentment and felt isolated, and then I realized I'm not actually giving clear direction of what I need. As in, don't bring me alcohol. When I'm in this really vulnerable place, a night out is not going to help me.
Also, I didn’t want to just riff about some mindless thing. Once I got comfortable with it, I would tell people, you can ask me about my dad. And to this day, six years later now, which is insane, people ask me all the time when I run into them in Kansas City, how's your dad doing?
On that note, how is your dad doing?
Thank you for asking. He actually did walk my sister down the aisle, and then walked me through the Teton (mountain range), for my wedding.
His rehab center even ended up doing marketing around his recovery. He’s like their show pony (laughs).
Just watching him, through his journey of asking for support, advocating for himself, doing his own due diligence and learning what he could control beyond what the service care providers were sharing… while that wasn't my injury, that was really, really formative and helps me reframe things when they feel tough.
Is there anything else you would like to share?
I would love to continue to support people with different abilities. Whatever we can do to fund more research, I’d like to do. If you’re interested in spinal cord injury research and support, visit Shirley Ryan AbilityLab.
If you’re interested in learning about business coaching with Sadie, you can submit an inquiry.
Thanks so much for reading — I’d love to hear what you think. Comment below!
Excellent interview, Anna!