Alright – so today we’ve got the honor of introducing you to Michelle Romero. We think you’ll enjoy our conversation, we’ve shared it below.

Michelle, appreciate you joining us today. One of the things we most admire about small businesses is their ability to diverge from the corporate/industry standard. Is there something that you or your brand do that differs from the industry standard? We’d love to hear about it as well as any stories you might have that illustrate how or why this difference matters.

One of the things we do differently at Dream.Org that I’m particularly proud of is, we actually try to solve the root of the social problems we tackle. As a systems-change organization, we aren’t focused on simply doing “good work” or work that feels good. We’re focused on moving the needle on the issues we care about. We’re focused on catalyzing a shift in the behaviors, practices, and industry norms that prop up and propel social inequities. By disrupting those things and offering an alternative, we focus on repatterning the world with new behaviors, cultural practices, and norms that work to create a more equitable future for all. There are many nonprofits that do incredible work. Unfortunately, most have to focus on treating the symptoms of our broken systems. We’re fortunate to focus more upstream to rewrite the rules and change the norms that lead to it being broken in the first place.

Michelle, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I am the Chief Strategy Officer for Dream.Org, a national nonprofit that dreams of a world beyond poverty, pollution, and prisons. We bring people together across racial, social, and partisan lines to end mass incarceration and build an inclusive green economy that can provide more freedom, dignity and opportunity. You could say we’re a bold, audacious group.

As the chief strategist, I design pathways to scale our impact and springboard leaders. For instance, I devised a strategy to scale our green economy program and effectively took a $900k/year program and turned it into an $7-8M/year program within two years, teeing it up to be a major player in the national climate scene. As a result, our team is now influencing national and even international conversations to build a more inclusive green economy that brings clean energy, good jobs, and critical local infrastructure to working class neighborhoods and communities of color.

Through the work of the programs I oversee, Dream.Org has helped 30,000 people out of prison, granted 500 scholarships to underrepresented talent to pursue tech sector and green careers, and recently shaped an $18B federal climate program to ensure that climate investments reach the people and places who need it most.

Drawing on my years of experience, in addition to guiding Dream.Org’s work, I now offer workshops and services to leaders across the industry who want to play bigger and scale their impact through my company We Create the Future, LLC. Learn more at itsmichelleromero.com.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Hope it’s your fault! I once had a colleague who told me that if something goes wrong, you better hope it’s your fault. I was puzzled by this statement. Who hopes it’s their fault? I certainly did not hope it was my fault.

I think most people are conditioned to want to succeed and therefore avoid failure. We’re certainly more likely to want to be perceived as effective, capable, and competent than not. The problem with prescribing any negative connotation to failure is that this leads us to gloss over how we may have contributed to the problem. If you view failure through a disempowering lens, your survival instincts kick in to do everything they can to convince you it’s not your fault and avoid responsibility. That’s a really difficult place from which to learn anything from the situation. In fact, you’ll likely repeat the mistakes over and over with that mindset.

On the other hand, if you view failure through an empowering lens and can evaluate, based purely on the facts, what did and did not happen that contributed to the failure, you can identify the exact moments, actions, and words that led to the failure. Some failures are not all my fault. Some failures may only be 2% my fault. But focusing on the 2% that’s within my control leads to new actions the next time that can catalyze a whole different chain of events and outcome. So as a leader, I hope it’s my fault because myself is something I’m wholly in control of. If we want the best out of our teams, I also believe it’s our responsibility as leaders to create a culture where it’s safe to fail and take accountability without judgement, so that employees truly learn from failures and the team can improve.

Can you tell us about a time you’ve had to pivot?

In 2021, Dream.Org decided it was a systems change organization. It was a critical moment for us in accepting our unique calling. We finally stopped trying to be like other groups who were doing direct service, collective action, or movement building work, and a whole new set of possibilities opened up. It brought new clarity of purpose to our work and fundamentally changed how we measure our success. It gave us a whole new lens through which to evaluate our work, which ultimately led to some important pivots in our Tech program.

We had a Tech program at the time that was focused on diversifying the tech sector. The core of the program was partnering with big employers like Target that had many tech roles to fill. We would recruit and train underrepresented Black and Latinx talent from nontraditional backgrounds for those roles. Then, after an 8-10 week intensive training program, most were hired by the company with starting salaries averaging $30,000 more per year than what they had earned just a couple months prior. Not only that, these were career track jobs where the earning potential was much greater. By all traditional measures, the program was a success, especially for the beneficiaries. We were truly changing people’s lives.

The renewed understanding of our purpose as a systems change leader, however, meant having to revisit the societal problem we were trying to solve and ask ourselves: Was this program moving the needle on that? And the answer was: No, not really. Our program was high touch, meaning a lot of time, attention and care went into supporting our participants. We hadn’t figured out a way to scale the program enough to be able to train the kinds of numbers we’d need to train to make a dent in the proportional representation gap that exists in the tech workforce. So, we pivoted. We decided to sunset our direct service job training program in favor of working with underrepresented founders on the cutting edge of climate solutions.

When we took a step back to consider the reasons we had been trying to diversify the tech sector in the first place, it came back to the fact that these jobs had become the new middle class job, and without accessible pathways into the “future of work,” the racial wealth gap would continue to widen. That’s why the lack of diversity bothered us. It was a sign that our communities were being left behind.

However, as someone who grew up in the 90s, I witnessed first hand how computers, the internet, and the digital age changed everything. Many of today’s wealthy elite amassed their fortunes starting or leading tech companies, or investing early in them. So as we considered how we could make the most meaningful impact and move the needle, we couldn’t forget the future. The next major employers will be green economy companies.

So, the pivot we made was to stop trying to play catch up by diversifying today’s tech sector and to start helping more underrepresented founders get in position today to leverage the current boom before us. In doing so, we believe we’ll be able to have a far greater impact on the racial wealth gap and securing pathways into the future of work with more equity-minded business leaders and inclusive workplaces practices.

It’s fortunate we did pivot our program strategy, too. The following year, we saw massive layoffs across the tech industry which would have made it near impossible for our entry level candidates to compete for remaining jobs. Meanwhile, we’ve managed to grow our Dream Entrepreneurs Network, providing critical resources and services to a community of underrepresented founders. Our offerings include helping them learn how to become investor-ready, connect with prospective clients and investors, learn how to draw down federal climate funding available for businesses, and partnering on bringing green economy solutions to underserved neighborhoods.

Contact Info:

• Website: Dream.Org / ItsMichelleRomero.com
• Instagram: @dream.corps / @itsmichelleromero
• Linkedin: https://www.linkedin.com/in/itsmichelleromero/

Image Credits
The one group photo in front of the Community Mobility Center should be credited to: Tim Daw Photography (https://www.timdawphotography.com). The other photos were taken by various staff members and do not need to be credited.