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Understanding the Past to Shape the Present: Reflecting on 8 Years as a Business Owner 

I truly believe that each of us deserves to have a career and life we love. This month, I celebrate eight years working for myself — over half of my professional career.  The key to my success started by simply understanding myself — my power, my influence, my why, and my reason for waking up each morning. 

I spent recent weeks reflecting on my winding path of social entrepreneurship. Looking back at the journey I took to become the CEO of Good Insight, a national executive search firm and governance consultancy serving the social sector, I realize nothing happened the way I expected. And yet, everything had to happen just as it did in order for me to build this thriving social enterprise.

If you are looking for advice on your career journey, I hope you’ll find these  lessons helpful.

Lesson One: Find a Niche  

In my early twenties, I thought I needed to understand nearly every role within the nonprofit sector. If I knew then what I know now, it’s this: People rarely seek expertise from generalists. Instead, pay attention to your strengths and carve out your niche. 

Eight years ago, I never considered launching an executive search firm. And yet, every single professional experience gave me the knowledge and networks necessary for nonprofits to trust me to find their next leader. 

Before consulting, I worked in philanthropy, which gave me a bird’s-eye perspective of the nonprofit sector. I cultivated grantee relationships across industries — education, the environment, arts and culture, housing, human services, and more. I loved talking to nonprofit leaders about their challenges, and was drawn to nonprofit capacity building and leadership development. 

In addition to my work in philanthropy, I chaired the board  of the Young Nonprofit Professionals Network (YNPN), helped initiate the Nonprofit Roundtable’s Future Executive Director’s Fellowship, and served as an informal adviser to the Obama administration on the Next Gen workforce. All before I was 30!

At face value, these experiences seemed unrelated (at least, at the time). Years later, I realized my niche was developing relationships — the perfect foundation for founding an executive search firm.

Lesson Two: Embrace Silver Linings 

I am a planner. My team jokes about my “photographic memory” for  systems, processes, and deadlines — never forgetting where we are within a given project.

Yet, there have been instances throughout my career I never could have planned but am forever grateful for. Never become frustrated by a curveball — instead, embrace the silver lining. It could be a blessing in disguise. 

Good Insight would not exist if my original career plans weren’t disrupted. In my late twenties, recruiters began to approach me about leadership roles at small nonprofits. That had always been The Goal  — to lead a grassroots organization where I could instill real change. But life had other plans.  

As potential dream jobs came my way, my husband was offered a two-year position in Berlin, Germany. I put my career  aspirations on hold to launch a freelance practice to sustain me overseas. My strong working relationships with former grantees helped me immediately find work writing grants for small grassroots groups, designing governance structures for multi-million-dollar nonprofits, and running cohort programs. At the same time, I served as a sounding board for past grantees and clients as they planned executive transitions, hired key senior leaders, and made their own career shifts.

Just as I returned to the United States in 2016, a recruiter approached me about a E.D. role. I went all the way to the final round and withdrew my name. Three years working for myself helped me realize that I could create more impact if I was the person running the search than winning the role. 

Lesson Three: Use Your Power and Influence 

I worked for myself for several years before I began identifying as an entrepreneur rather than a freelancer. As a small business owner, I faced imposter syndrome and felt as though I should have more knowledge and confidence within my area of practice.

My clients knew I was passionate about nonprofit leadership development and began calling upon me to support succession planning for upcoming executive transitions. Just as I began designing an approach to executive search for small nonprofits, the Building Movement Project released Race to Lead, a study that examined race and leadership gaps in the nonprofit sector. Their research showed with absolute clarity that the lack of diversity in the sector is because of persistent bias that systematically weeds out qualified candidates of color, rather than the commonly assumed lack of aspiration among BIPOC rising leaders.

The results of the 2016 election had already initiated a period of self-assessment for me as I thought through how I could align my commitment to racial and social justice to how I showed up in my work. This period of internal evaluation showed that I was pretty far from where I wanted to be. I took on a significant process of self-discovery, personal healing, and planning for how Good Insight will dismantle systems that prevent leaders of color from advancing into executive positions.

I shifted from not knowing a lot about growing a business to understanding where my particular power and influence in this work comes from. As a white woman who has worked in philanthropy, I have been at the right tables. I have access to the people and networks that are necessary to create change for the sector. I can put my business’ resources behind me to create solutions.

I encourage all of you — no matter what stage of your career you find yourself — to use your power and influence for the better.

Lesson Four: Self-investment Pays Dividends

When I first launched my business, I held a scarcity mindset (a hurdle faced by almost every business owner, ever). Finally, I made the decision that if I wanted Good Insight to grow, I needed to make some major investments — both in myself, the business, and my team.

First, I became incredibly clear — both in internal and external communications — on who we are, what we do, and who we serve. Our ideal client is a community-based nonprofits (and the associations that support them) with a budget under $5M. Their biggest pain point is facing the transition of a founder or long-term executive director, or hiring a senior leader. 

This crystal clear message not only made it easier for folks to refer me (over 80% of the business comes from referrals), but it allowed me to elevate the Good Insight brand. We built the Good Insight brand through an updated website, consistent communications (like Good News, our monthly newsletter), and social media posts. Targeting clients across multiple channels allows me to stay top of mind, while serving clients, partners, and former clients with educational resources. 

Finally, I had to accept that I simply cannot do it all. I intentionally built a team of professionals who brought new skills and knowledge to Good Insight, all while reinforcing our shared values. Expanding from a single business owner to a team of six hasn’t been easy, and there have been some missteps along the way. However, each lesson helps refine the skills, attributes, and values we look for in a new teammate. 

I hope these lessons can be helpful to you as you think through how you want to build a career and life you love. With a clear niche, an open-mind, a sense of purpose, and investing in yourself, you will be well on your way.

Thank you all for your support over the past eight years, and I look forward to continuing to keep you updated on our progress as we increase our impact across the country for years to come.

All my best, 

Carlyn Madden

CEO, Good Insight 

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