We had the good fortune of connecting with Jennifer Seybold and we’ve shared our conversation below.

Hi Jennifer, we’d love to hear about how you approach risk and risk-taking
I think we talk about risk a lot when we talk about big success stories. It’s become a huge topic in business and it’s become somewhat synonymous with those who enjoy business success. We’ve all heard the saying “No risk. No reward.” And when our minds reflect on the truths behind this statement we think of those impossible stories – the man who mortgaged his family home to start a business that made him wildly rich a year later, or the woman who quit her job after 20 years to start a fashion line that’d not an international brand. These stories inspire us, and these are the stories we often lean to when we ourselves are looking at risks and the rewards we might reap in our own lives. These are great stories, but I think we look at the risk all wrong. We think the risk was losing that steady income job of 20 years….I’d ask people to consider that the risk was actually on the other side of this story. What were the risks this woman would have been taking if she’d stayed? That’s where the real risk lies. Those leaps we take that we call risk, they’re often actions to mitigate an even greater risk. Yes, we take a chance when we make a change like those I’ve talked about here, but the risk of not taking that chance is the real risk. What we are really describing here is looking fear in the eye and taking the right step forward.

Risk is an inevitable part of all of our lives and careers, what’s perhaps not is facing those fears. This has played a huge role in my adult life and career. I became a mother at the very young age of 17. That was a space of tremendous fear, fear I’d never felt so deeply to that point in my life. But on the other side of that was a deep desire to be a mother that had always been a part of me. The timing of course wasn’t what I’d planned in my life and it would mean that the year ahead of me would look drastically different than I’d planned. I think a lot of people thought that choosing to be a mom at such a young age was a big risk. It was big, that’s for sure! But for me it was a step forward into the life I wanted and the risk would have been not facing that fear and moving forward despite knowing the road ahead would be challenging.

My career would take a different path than I originally envisioned. I didn’t move to New York City and become a writer. I stayed in my hometown and worked in a corporate start-up. I was perhaps one of the few back in 2003 working in an entirely remote job from home. Though it wasn’t what I’d envisioned, I was good at it and I loved the freedom it gave me to live my life the way I’d wanted to with my family.

By 2008, I was raising three young girls who were all starting school and I decided the time was right for me to do the same. Again, the risk would have been not to. A part-time student that journey would mean five years at a community college, followed by a devastating divorce and custody battle, a year to collect myself, and in 2016 the completion of my degree in Organizational Leadership with specializations in Nonprofit Management and Small Business Entrepreneurship. During the time that led up to that day I’d worked a corporate job for more than ten years, I’d done a little small time modeling, done medical coding in a small office, taught as an early childhood education teacher, worked in a college foundation, as a non-profit consultant, and in a series of other part-time jobs that led me to where I am now.

Since 2016, I have worked as a non-profit Executive Director with organizations serving individuals experiencing homelessness – first at Cold Weather Care in Adams county and most recently at the Denver VOICE. It’s a mission very close to my heart that has been wildly rewarding, but that has always been a place I have been incredibly successful – in my most recent role expanding the organization’s budget by more than 500% from 2018-2022 meaning far greater community impact and possibility going forward. And as I head into a new role with Veterans Community Project of Longmont, I’m excited to have that kind of success again as the organization builds its first national expansion site right in my hometown.

Risk has been an unavoidable part of my life and career. What I have learned over the years though is that when you feel that terrifying, excited but uneasy feeling in your gut, the risk isn’t in taking that next leap forward…it’s in sitting still. What being willing to recognize risk in my life has given me is a life rich with three incredible adult children, an amazing partner, and a career that has made that life richer with meaning and success. I hope what I have taught my children is that so long as you recognize the risk of sitting still and know you are capable, the only risk that exists is not taking the next step because staying in a place where you feel comfortable but where your heart longs for more…that’s far more risky than what we often hear called risk in our society.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
My career has been one filled with many different paths. What sets me apart from others is that there’s been no straight line to my getting here. It’s been a crazy zig-zag path that has led me to all types of different work and has helped me to develop a set of skills more varied than most people ever get the opportunity to experience.

At 18 years older I was working at a start-up fully remote, doing client research and pulling public records to support our leads team. In between public record searches and filing reports, I was nursing and playing hide and seek. By 22, my children were growing and I was going to school, and working several roles part-time while moving on a path that would unexpectedly take a few turns along the way. Before I would finish my degree I would develop skills in corporate research, medical billing and coding, child development, executive assistant work, grants, customer relations, and so much more. It’s my belief that this uneven pattern over many years is what has led me to find the work I truly love doing. It has also prepared me to do almost anything! When you’re a single mom of three, working as many jobs as you have children, your confidence in taking on new challenges is essential.

My path has been anything but easy, but it has taught me who I am, what kind of leader I am and that no matter what comes I’ve got it.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?

Denver is filled with great spots to eat, drink, and see! But I’d want to make sure that my friend experienced not just the usual places, but the spaces we forget are a part of our city, or perhaps those many of us don’t even know exist.

Sunday – I’d start out Sunday with a Denver VOICE tour of Five Points with Mr. John Alexander. If you don’t know about this tour check it out! It’s part Five Points history and part personal history from someone who lived it. You’ll learn a lot about the area and the chance it has seen over the years and you’ll have a lot of fun getting to know John who is a local legend himself. And after we’d finished our tour, lunch at Welton Street Cafe – one of the few historic spaces still in existence in a changing neighborhood.

Monday- We’d walk around Union Station and people watch. Catch lunch at Ultreia and enjoy some time in the sunshine on the patio.

Tuesday- Visit the RiNo neighborhood that is ever changing and enjoy an afternoon of food tasting and drinks from Epic, Block Distillery, and Stem Cidery.

Wednesday- Take some time to volunteer with a local organization. Serve meals at Haven of Hope and distribute papers at the Denver VOICE. There are few places you’ll find such positivity in your day-to-day life than here. I am always amazed and impressed at the outlook the individuals in these programs have despite far greater challenges than most of us have faced in a lifetime.

Thursday- Shop and explore Highlands Square, Tennyson, and Low-High. Finish up with happy hour at Postino – the cheapest happy hour around with a great selection of wine and food!

Friday- Explore Broadway sights and sounds, stopping into some of the local shops and finishing up with a rooftop meal at Historians Ale House.

Saturday – Hike in Red Rocks and take in the stage at what has been described as the world’s greatest outdoor amphitheatre.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?

If not for my children there’d be very little for me to give a shout out for. Being a mother has made me a stronger, smarter, fiercer risk-taker in every sense of the way we define it. My wish for them is that they know how they’ve changed me, they know their own incredible capabilities, and that they know without a doubt they will land on their feet no matter what comes their way. This is what they have taught me!

I’ve also been really fortunate along the way to have a wonderfully supportive family. My mom and dad, no matter how misguided or risky they think my choices might be, have always supported the choice to live my life as I want it and they’ve been there along the way to help pick me up and cheer me on.

And, my partner Chuck. We met almost eight years ago when my career but also my life had taken a pretty dramatic swing. Without his belief in me it would have been hard to accomplish what I have. His pride in my success today is a gift.

Image Credits
Giles Clasen – Denver VOICE Contributor Ad2 Colorado Campaign

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