Alexis Wiggins Jonathan

My success comes from bringing direct-service instincts into tech operations — the kind you develop in classrooms, shelters, and being in the community. That background taught me to meet people where they actually are, not where you assume they are or should be. That’s how trust gets built. Once you have trust, you can understand the complexity of a situation — the competing priorities, the messy middle, the things that don’t fit neatly into a playbook — and actually move through it together. Everything I’ve built professionally traces back to that.

I dont have one clean piece of advice but there is one phrase that’s pushed me further than any mentor or coach ever has. It’s been thrown at me nearly every place Ive worked: “You’re too smart for your own good”. It took me years to realize it was never about my intelligence - it was about whose comfort my intelligence was disrupting. Once that finally clicked I was able to stop performing and contorting myself for other peoples comfort - they were never going to validate my value. Now I put that energy into bringing value, earning trust and delivering results.

My advice is to get honest with your self-talk — not to spiral, but to decode it. What are the intrusive thoughts actually telling you you’re afraid of? Mine were: you need the health insurance. Working for yourself is too unstable.

So I looked at the evidence. My last job had layoffs, RIFs, and acquisitions looming constantly. That’s not stability — it was a different flavor of precarious. I’ve been on my own for six months and things are just fine. The stressors are the same — money, kids, time — but now I’m free to take care of myself and my family when and how we need it. Nobody is capping my potential. Nobody is critiquing how nice I am.

I was never afraid of failing - that would have just proved my thoughts right. I was afraid to free myself from everything else. I had to stop should-ing on myself and force myself forward.

If I’m being honest, the biggest challenge in my field — and I’d venture to say many others — is security. We’re told to stay versatile, gain credentials, prove your value. And it often isn’t enough. The pace of change is overwhelming. When you compound those challenges with personal identity — being a woman, being a person of color, being disabled, or queer — things can feel insurmountable.

And then you look around and realize the ground isn’t just shifting on its own. The boys club is back with a vengeance — and it is not a good time. I watched it happen in real time: every woman in leadership who left my last company was replaced by a white man. Nearly every person of color, replaced by a “better culture fit”. That’s not a coincidence, that’s a pattern. When discrimination starts feeling like policy again, it stops feeling personal and starts feeling structural.

Structural problems require time and a whole lot of effort and commitment to resolve. Terrain is my personal response to that. I’m building something based on my skills, capabilities, and experiences — not solely my identity. It’s how I can continue to do the work I crush at, spread the impact to others, and promote good business.

That’s the greatest opportunity right now — for those of us who have been pushed out despite our talents to build the kinds of businesses and cultures we actually want to see.

The values I bring to my work are ones I’ve chosen deliberately. Truth and transparency, even when it’s uncomfortable — because you need that to build trust, and trust is the foundation of everything. Vulnerability as a leadership practice. We don’t have to cry at every meeting, but people trust people. Making space for that is part of the work. And I don’t believe in doing what’s “best for the business.” Organizations are made up of individuals. Do right by them, and good business follows.

On a personal level, I’m all about slow crafts and living sustainably. I weave, garden, cook, sew — anything that requires time and intention and cuts screen time. It’s how I stay healthy and grounded, when I do my best thinking, and what keeps me present with my family.