The Founder Reflects On The Inaugural Year

The first year ‘On the Road’ has been an adventure. Here are 5 reflections from Brent Holsinger, the founder and president of On the Road Collaborative, about our inaugural year.

Go carefully, but go.

I recently read a quote that said something like if you wait until you have it all figured out before you get started, you have waited too long. I found this to be true in launching On the Road Collaborative last August. We decided on a 2-day per week middle school program model to start, centering on our Career Enrichment Projects. While we knew that we would eventually want to expand to a 4-day per week program, we believed we could have a positive impact, and then expand and improve upon what we started in future years. This has held true. This past year, we served more than 100 middle school youth, solidified our focus on Career Enrichment Projects, and are now positioned to grow to a 4-day per week program, expanding our services and more fully meeting the needs of our youth and families. It was important that we said “Go” 10 months ago, and didn’t wait until we had everything we wanted, because I believe we would still be waiting. And, as we look to solidify our core Career Enrichment middle school program this year, we will be launching a new pilot 8th Grade Academy high school readiness initiative for a cohort of 20 youth (thanks, United Way). Go carefully, but go!

Brent and Deanna smile for a photo

Find your Robin.

There has not been a greater sense of joy and strength as serving alongside Deanna Reed (OTRC Program Director) this year. Batman and Robin needed each other. They were the dynamic duo. Neither one of them would have been as good if they were on their own. I have found tremendous strength and comfort in having a partner, someone who I knew was with me every step of the way and is just as committed to the success of On the Road as I am. 

Don’t get me wrong, having a partner, particularly if they are the right one can be maddening at times, but I believe therein lies the beauty. I have found that we complement each other’s strengths and weaknesses, bring unique insights and ideas, and push each other to be our best selves, which strengthens our work on behalf of On the Road Collaborative and all those we serve.

On the Road team celebrates their first year

Celebrate your victories.

I made a point this past year to acknowledge and celebrate our victories. We celebrated our young people at Learning Showcase events across the city, individuals deciding to join our board of directors, donors renewing their support for another year, the incredible service of our volunteer Community Teachers, numerous grant awards, among other accomplishments. Each one was special and served as another step forward down the road.

And while we had many victories in our first year, we have had many more moments of rejection, struggle or failure that had the potential to discourage and break our spirit if not having taken time to be encouraged by our victories. Be encouraged in your victories, find ways to build upon them, and make efforts to learn from your mistakes and shortcomings so that those may become next year’s accomplishments. In summary, make time to wear party hats, blow on some noise makers and smile. (Thanks to i love my burg for this photo and for providing encouragement and affirmation to so many in our community).

Don’t go faster than you can stop to say thank you.

One of the most difficult things for me is the temptation to do too many things at once or too quickly in order to grow faster. Many a times I have talked to our current board about how quickly we should grow the board of directors. We are currently at 12. Naturally, it makes sense for us to jump to about 18 next year and 24 the following year, right? Naturally. Another key lesson from this year is how important it is to surround yourself with incredibly smart, talented and experienced people to keep me from doing stupid things. In case you were wondering, we will be growing the board by 2 members next year, which I believe is perfect (announcement coming soon). The idea that has helped me the most to find the right balance is to only go (or grow) as fast as we can stop to say thank you to the people who make it all happen. It is a constant tug to be searching for NEW volunteers, NEW donors, NEW champions for OTRC and the young people we serve. However, I never want to grow faster than we are able to stop and say thank you, and appreciate all those individuals who have been on the road with us and have helped us get to the point where we are now.


Clarify your message.

I realize more and more how much I like using words and how they don’t always come out clear, concise and engaging when I share them the first time. I think some of it is simply how my introverted self processes information in sort of a squiggly line, compared to a straight one. What’s that quote, “If I had more time, I would have written a shorter letter.” I’ve been diving into Donald Miller’s Storybrand process in recent months, and absolutely love it. Miller’s framework has helped me begin to understand how to clarify our message about what we do at On the Road Collaborative in ways that are clear, compelling and memorable. For instance, the tagline on the main page of our website used to read, “On the Road Collaborative is a 501(c)(3) youth empowerment organization. We empower underserved youth with the opportunity, skills and confidence they need to
excel in school, be on track for college & career and fulfill their
​promise”. It now reads, “On the Road Collaborative is a non profit youth empowerment organization that sets middle school youth on the road to college and career.” Both are accurate. I believe the second version gets us closer to where we want to be. We provide a lot of opportunities for our middle school youth from academic coaching to career enrichment projects to college visits to mentorship yet I am finding it more important than ever that our message inspires citizens from all corners of our community to join us in empowering local youth.

As our friends at VA Momentum would say for their upcoming Growler Team Relay (sign ups still available!), year 2 is sure to be a “mix between a road trip and marathon.” Can’t wait! We hope you join us.