We caught up with the brilliant and insightful Jessica Gleim a few weeks ago and have shared our conversation below.
Jessica, looking forward to hearing all of your stories today. Can you talk to us about a risk you’ve taken – walk us through the story?
When I was just 26yr old, I was diagnosed with Trigeminal Neuralgia (TN), also known as “the suicide disease”. TN is basically, unbearable facial pain. My life as a newlywed, new homeowner and a new doggy owner quickly became a living nightmare. And at the same time, I was also working my dream job – as a graphic designer for a new brand under the designer stationery series with Shutterfly.com.
Side note: In 2009 it was my claim to fame when the Jonas Brothers bought my Christmas card design and it was featured in the Huffington Post 🤣 (I have the graphic image from the Huff Post if needed!)
As a sophomore in high school, I decided I wanted to grow up and become a graphic designer and I wanted to figure out how I could work from home, be a mom and take care of my kids while also having a fulfilling career. Everything came to a screeching halt when facial pain took over my life. I felt like I was right on track to building my family, having my dreamboat job, and living my dream life. And then it all went to shit.
The medication for TN are all drugs that you cannot get pregnant on, and all meds with big side effects. Trying to find pain relief to just function, let alone work, was rough. I was quite frankly a mess. In 2012 I even tried brain surgery (called Microvascular decompression) to fix my TN but it didn’t work. My dream life felt like it was falling apart. My future seemed non-existent. The meds didn’t 100% take the pain away, and they also made my brain and body feel sluggish and gray. It was hard to remember things, hard to do anything. I have a distinct memory of thinking, how do people get so much done – when I could barely take a shower or eat? I couldn’t keep up with life, let alone work. I needed a sabbatical, but we weren’t prepared to live on one income. This wasn’t the plant. My beloved therapist told me to do it – to quit. To take a break, to take care of myself and to focus on finding healing, and then when I’m ready to start my own business and work for myself. I felt so much shame and guilt quitting and giving up work. My dad was incredibly nervous about it and voiced his concerns. How was I going to make up that income? My husband was 100% supportive as he always is, but I’m sure he also felt totally uneasy. Somewhere in the back of my mind, I knew that if I could just take a breather and just focus on my health I could figure out how to get better and make it all work. And somehow I’d come back better than ever.
A few months after starting my health sabbatical – people started asking me to do little design projects here and there. At the time I was researching disability. I knew that I could never go back to working full time, my body and my nerve pain just wouldn’t let me. Full-time, working for someone else wasn’t going to work for me. I met with a disability lawyer and learned that at the time, the most you could make if you worked was $800 per month. And I figured even if I felt like absolute shit, I could make more than $800 working from home, in my bed. So I took a big fat chance and opened up an LLC.
In the last 13 years – I’ve gone in and out of remission from TN several times. I’ve been able to have two beautiful boys in the remission seasons. I’ve built a thriving advertising and consulting agency (design took me to digital marketing, and digital marketing took me to my passion for social media advertising). I’ve built a team. I’ve built a family. I’ve built a beautiful, fulfilling, authentic, and happy life.
Jumping off the cliff – taking the risk of betting on myself – and truly trusting myself, has led me here. My family, my 15+ year marriage, my children, my work, and my business – are all physical proof to me, that the Universe has my back. And all I need to do is jump. No matter how scary, no matter how much pain, no matter how uncertain, I just need to trust myself that I can figure it out and just jump.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I’m an incredibly passionate entrepreneur who helps online business owners use social media advertising to make money. I love social media and the internet (it is a blessing and a curse) – I absolutely LOVE digesting content. I’ve watched countless girlfriends use Instagram and Facebook to build incredible communities and figure out how to monetize them authentically, and make significant income, all while doing it from home with children. I hate that women and mothers seem to have limited options – 1) stay at home with their kids, because the cost of childcare is insane 2) full-time work out of the house which can make it really hard to support your family/children’s needs 3) join an MLM. My passion for online business comes from my passion and drive for supporting women making real money, and doing something they love while taking care of their kids – and the internet and social media is the platform that provides those opportunities.
In addition to that – I’ve also always been obsessively curious about why people make choices to buy things. Which was my initial love of design. It’s the concept of why people choose to shop at Target vs. Walmart. Because it looks and feels “better”. Combining these two loves, created my curiosity and passion for social media advertising. I started running Facebook ads about a decade ago and started running them for my own marketing clients. In 2019 I gave a talk at Alt Summit about ad strategy (I like to explain it like online dating – you cannot show a person one ad and expect them to buy immediately, you have to date your customer before you ask to marry them) and it clicked – ADS. I wanted to niche down to just doing paid social ads and strategy.
In my work, I help primarily ambitious women online business owners and brands use social ads effectively to create revenue. Ads are complex and convoluted and I like to make strategy easy to digest, and clear for my clients as to how it’ll impact their bottom line and long-term revenue and business growth.
What’s a lesson you had to unlearn and what’s the backstory?
I’ve never had a lot of self-confidence when it comes to being “smart”. I have two older brothers who excelled in AP classes, and I didn’t really excel at anything in school except talking. When I was in elementary and middle school I was pulled out of my main class to go to special reading classes. I was always at the lowest level of math, language, etc. So I just never had a lot of experiences to really support that I am actually smart.
Until I started my own business and became 100% self-taught, through trial and error with digital advertising. Through running my own business, I’ve learned to be open and remain curious. And to look at every situation through a growth mindset lens of “what am I learning here”. It has served me WELL. Now at nearly 40 years old, I’ve learned that I am smart and capable. I just never knew how I “learned”. In owning my own business, I’ve had to make it up as I go along and it’s put me in situations where I can excel because – I need to literally DO IT, go in and make a mess not knowing what I’m doing, in order to figure something out. And that is truly being an entrepreneur. I’m very very comfortable not knowing the answer and just diving in with both feet, trying to figure it out.
I am very smart and very capable. I have been all along. I just need to actually be in the situation, doing the damn thing, watch the video, write out the notes – do all of the learning styles – to learn. I’m confident now knowing I can just get in, make a giant mess and then come back and clean it up once I’ve figured things out.

Can you tell us about a time you’ve had to pivot?
I’m pivoting right now.
For the last 5 years I’ve spent my professional time building a team and systems and processes to support a growing agency and clientele – working primarily with DTC ecomm brands. I’ve known this the entire time, and I preach this to our clients but it’s a terrible idea to have one primary source of revenue. For example – the Apple iOS 14 update changed a lot of things in regard to FB ads and a LOT of DTC ecomm brands relied heavily on cheap, efficient, easy ads to generate new customers – and that was the primary source of revenue. And then BOOM, Apple does this big privacy update, completely changes the landscape of Meta ads and so many brands have lost their revenue-generating machine. And we saw this with clients of ours as well.
Well – I never was able to take my own advice. The primary revenue source for my agency has been big private client work. I’ve always known we need to diversify, figure out smaller packages or other types of clients, more coaching, courses, programs etc. DIVERSIFY. But I couldn’t find the time to figure it out – as busy mom and wife and leader. I had my 2nd baby in August and within the span of about 10 days, multiple clients had major major major complicated situations take place that forced them to stop all advertising and their agreements with us. And boom – my bottom kind of fell out. I thought I’d be able to hold out for several months with enough cash reserves and bring things back but that hasn’t been the case and sadly I ended up having to lay off several people and downsize. All while experiencing this incredibly special, amazing time in my personal life with my new baby.
But sure enough, I’ve been able to figure out so many things and a better way to move forward. All while taking care of my son without any extra childcare. It’s been really incredible time. Highs and lows. I’ve always been moving a mile a minute the last 6 years as an agency owner and mother, and I haven’t had a chance to slow down. Slowing down has to led me to figure out a better direction for my business, in the ever-changing landscape of digital advertising. Where I can provide an even better, more efficient, and long-term profitable offering. I’m ultimately moving away from big agency model and moving into ad strategy and creative consulting. It’s no longer affordable for ads to be run by an outside team for a big majority of business owners (if your ad spend is say less than $100K per month). What matters today is ad creative AND the strategic plan of how your ad results grow your business outside of solely selling and new client acquisition. Paid social, along with platforms, algorithms, how and why we buy, etc move and change SO fast – I ultimately think this all has happened to me for a reason, to force me to pivot professionally.
And from a personal standpoint – what a blessing it has been for me and for my family to have some more time to focus on our baby, and our 6yr old, and our home. I’ve really been able to figure out the family systems we need to function as a family of four and take time time to really transition into my role as a mom of two. I’ve been really cherishing it all while figuring things out with my business a day at a time. (With my first child, I had taken on two incredible client opportunities while I was pregnant, one of which the week before I gave birth and it’s just been GO ever since).
Contact Info:
- Website: www.jessgleim.com
- Instagram: @jessgleim
- Other: Tik Tok: @jessgleim
Image Credits
Professional images from Calviana Photography Otherwise their personal photos

