The Evolution of Insight—and of Me

May 27, 2024

Back in 2016 when I started volunteering in prison, I didn’t think I’d ever start a non-profit. I thought I’d volunteer my time running groups and then find other ways to make a living.

Running a non-profit seemed like a lot of work and required too many skills that I didn’t have. What did I know about creating a budget or writing a grant? Literally nothing. I just knew how to create a safe container for people to wake up and realize more of who they really are. The rest of it felt out of my wheelhouse. Then one day, a friend of mine said to me, “but what if you can do it? ‘What if it’s not as hard as you think?’” That was all it took for me to see how much thinking I had about starting a non-profit. And I was like, “Ok then, Fuck it. why not.”

The thought that was harder to shift was, “yeah, but I’m not a leader.” I knew I really wanted to be in the classroom, but didn’t really want to do the rest of it and didn’t think I was capable. But when you have to do the rest, you do the rest. I learned how to write grants and understand simple budgets. I could do basic operations, but at that point it was just me, so I didn’t have to manage anyone and I’ve managed myself my whole life so no great surprises there. 

However, I’d often surprise myself by being able to do more than I thought I could do. At this time, we had some amazing volunteers who I trained to teach our Insight to Wellbeing program. Because I’d trained these volunteers, I needed to create something that they could loosely go off of when teaching. That’s where myself and a few others got together to create what is now the Insight to Wellbeing curriculum that we get to share in various different places. In addition, I learned how to write proposals and get shit done. I think if there’s one thing I know I’m good at, its getting shit done.

We were soon able to hire an operations manager so I could off-load many of the things I didn’t love to do. Now I’m back to do doing what I was good at—teaching and running groups. When the time came, I decided to pass on being the Executive Director of our organization. It was something our operations person really wanted and I didn’t think I wanted it, so I became solely the program director. It felt comfortable. It allowed me to focus on what I did best. 

The organization continued to grow as we went on. Truth be told, we grew too fast. At the time, we were being offered a lot of opportunities, including grants to expand our work to include mentors, housing, case management and restorative justice. It all felt so right at the time. It felt so aligned with the heart of this organization, Insight to Wellbeing. People need case management, mentoring support, and even housing when they come out of prison, so it made perfect sense for us to take up all of those opportunities that were coming our way. The Restorative Justice made sense. Insight to Wellbeing felt like the perfect precursor to restorative justice. Understanding your mind and your internal climate feels essential to finding connection, forgiveness and resolution when you’re in circle with a person who’s caused harm and with the person whose received harm.

One thing I’ve learned over the last 7 years is, just because we’re being offered an opportunity to do good things doesn’t mean we should take up every offer. Growing fast isn’t necessarily a good thing. In fact, slow and steady is often times the more sustainable option. But here’s the thing... To learn and grow, sometimes we have to make mistakes and try things that feel good in the moment for us to get to the next level of understanding what works best, and then course correcting when necessary. 

I’ve eaten my fair share of humble pie the past couple years. I’ve learned more about myself than I thought possible in one life time. I’d unconsciously recreated old patterns of deferring to strong women in my life and playing small to protect others feelings. Fortunately, I’ve had some huge insights that helped me see once again, these very outdated themes that seemed to reoccur in my life. Sometimes, you can’t see what you can't see until it hits you over the head with a two by four! It had little to do with the people I worked with and more about me picking up my own leadership. It’s amazing how much energy can get released when we pick up a side of ourselves that has remained dormant or hidden for way too long. 

Now, things are changing. After years of thinking I’m not a leader, it’s not who I am, I’m realizing for the first time, it is. I’m excited to be fully stepping up and taking on the role of Executive Director in the organization I started back in 2016. It feels right. I’m already getting a crash course degree in nonprofit management and operations. By now, you’d think I’d have it down, but I haven’t. I abdicated some of those responsibilities because it wasn’t my job as a Program Director. Although I’m not proud to say, it was honestly more comfortable to stay out of the way sometimes. 

Fast forward to now, we’re embracing a full re-imagining and re-creation of The Insight Alliance. An Insight Alliance 2.0, if you will. One of the things we’ve realized as an organization is that we operate best when we’re collaborating and making collective decisions, not when we work in silos. We’re re-embracing the meaning of ‘alliance.’ We know this will be a full team effort in collaboration with our incredible board, amazing co-workers, and community partners.

 Our team knows how important our work is and it’s been beautiful to hear from key stakeholders about their enthusiasm and passion for the unique and powerful impact our work has in the community and we’ve been blown away by the amount of support we’ve been receiving these past few weeks. We all feel grateful and super excited to embrace this creative journey together.


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The Web We’re Born to Weave

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Everything Went Wrong—and It Was Still Right