10 Years of Signify: Lessons from a Fractional CIO

I can't believe it, but this month, Signify turns 10 years old, and it feels like a good time to revisit the version of this post I wrote at year five.

It's also shaping up to be a year for history-making well beyond my own small business. America turns 250 this year. I'm writing this from Hawaii, which happens to be the 50th and final state on my list to visit. In September, I turn 50. When that many milestones line up at once, it stops feeling like coincidence and starts feeling like an invitation.

Part of reflecting on history, whether it belongs to a country, a state, a person, or a business, is learning from it.

So, in honor of Signify's 10th year, I want to share 10 (of the many . . . ) lessons I've learned along the way.

1) Success Is a Relative and Fluctuating Term.

Sometimes it looks completely different than you imagined when you set the goal, and sometimes you reach it only to immediately set a new one.

Ten years ago, success meant landing my first clients and simply making rent from freelance work. Today, it looks like a decade of relationships, a body of work I'm proud of, and the kind of lessons that only come from staying in the game long enough to learn them.

By the way, there is a terrific little book called The Dream Giver that illustrates this and I have thought of many times over the years.

2) Being a Business Owner Means Constantly Learning New Things.

Just when you think you've mastered one skill or role, the job shifts and asks something new of you. I've been a strategist, a copywriter, a bookkeeper, a salesperson, and a student, often all in the same week. The moment you get comfortable is usually the moment the job changes again.

I remember asking multiple people after the first couple of years if the feeling of “flying by the seat of your pants” ever goes away. Their answer: Nope.

And a decade into it, I agree.



3) No Matter Your Age or Stage, You Need Peers and Mentors to Get You Through.

Ten years in, I still lean on both, and I don't expect that to change. The specific advice I need has shifted over the years, but the need for community around me never has. To be honest, I think it gets harder to ask people questions, and to feel like you need to have all the answers. But I think the smartest people continue to ask questions.

If you're still building that group of people, The Networking Matrix is a good place to start.



4) Nothing Great Is Accomplished Alone.

This holds true even—or maybe especially—when you're the only name on the door as a solopreneur. Behind every project I've delivered are clients who trusted me, collaborators who filled in my gaps, and a community that cheered me on when I needed it most. Asking for help is not a failure of solopreneurship, it is a requirement of it.



5) Small Teams Are Often the Most Creative.

They find unique and innovative ways to accomplish their mission, often because constraints breed ingenuity. When you don't have the budget or the headcount to do something the obvious way, you find a smarter way instead.

6) There Are More Similarities Between Large Organizations and Small Ones Than Most People Realize.

No one believes they have enough time, money, or help, regardless of their budget or headcount. I've worked with organizations of every size, and the conversations about capacity sound remarkably similar no matter how many zeros are in the budget.



7) Marketing Keeps You Busy, But Strategy Is What Drives Momentum.

It's easy to confuse motion with progress, and only one of them actually moves you forward. The organizations that grow are rarely the ones doing the most. They're the ones doing the right things on purpose.



8) Facts Are Necessary, But Stories Lead to Action.

People remember the story about the person you helped, not the statistic behind it. If you want someone to act, don't just tell them what you did. Show them who it mattered to. Learning to communicate that clearly is a skill, not an instinct, and it is one worth practicing.



9) Non-Profit and For-Profit Organizations With a Social Mission Are Among the Hardest to Market.

That's because of their diverse stakeholder groups. Congratulations to everyone reading this who does that job well, every single day. You're managing the expectations of funders, customers, boards, and communities all at once, and still finding a way to tell one coherent story.



10) The Work of Impact Is Hard, and It's Also the Most Rewarding Work You Can Do.

It's draining, complicated, and pressure-filled. Ten years later, I wouldn't trade it for something easier.




So, what's a lesson you've learned in your own year one, or your own decade? I'd love to hear it in the comments.

Thank you for reading, for supporting this work, and for doing your own good in the world for the last 10 years, however long that's been for you. If you're curious what it looks like to have this kind of support on your own team, start with What is a Fractional Chief Impact Officer?



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I’m Kristi Porter, and I help cause-focused organizations move from scattered efforts to strategic growth. As your Fractional Chief Impact Officer, I’m here to help you measure what matters, communicate results, and maximize your mission—all on your terms and budget. When you go from overwhelm to outcomes, you can do good even better.