About Cari O’Brien, Minnesota Lawyer, Coach & Speaker
You’re building something that matters—whether it’s a business, a legacy, or a life aligned with your values—and you want the right people beside you as you do it. You especially want someone who listens deeply, thinks strategically, and brings both heart and expertise to the table. That’s where I come in.
Insightful. Strategic. Warm. 100% Real.
Hi, I’m Cari! Whether I’m walking alongside you as your coach, counselor or event co-creator, you’ll get the same thing from me every time:
🌀 Clarity
🌀 Care
🌀 Momentum
You bring your vision—I bring a head full of strategy, a heart full of empathy, and a plan to help you move forward. You can also count on the following when we work together:
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Clear, Responsive Communication
I believe strong relationships are built on transparency and clarity. As a seasoned writer and speaker, I place a high value on communicating with purpose and care, so you’re always informed, aligned, and confident about our direction.
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Creative Strategy
I’m equal parts big-picture dreamer and tactical problem-solver. I’ll help you see the forest and the trees, and then guide you in mapping the clearest path through them.
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Authenticity & Professionalism
I show up as my whole self in every engagement; I don’t leave parts of myself at the door, and I hope you won’t either. I also know how to read the room, lead with integrity, and match the tone to the moment. Clients often describe me as warm, insightful, efficient, and trustworthy.
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Empathy in Action
Whether you’re building a legacy, navigating a loss, growing a brand, or refining your message, I meet you where you are with genuine presence and a focus on making your next step more manageable and more meaningful.
My Professional Journey
I’ve never followed a straight-line path—and I wouldn’t have it any other way.
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I began my college journey as a theatre major at Macalester College, dreaming of life on stage. But as I immersed myself in performance, I found myself drawn more to the bigger stories shaping our world. Shakespeare’s reminder that “All the world’s a stage” rang true for me, just not in the way I first imagined.
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So I pivoted, earning a double-major degree in Sociology and Political Science while setting my sights on human and civil rights work. Law school followed—first at Seattle University School of Law, then at William Mitchell College of Law (now Mitchell Hamline). I focused on social justice and international law, and began my legal career advocating for second-chance policies and systemic reform.
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When funding for that work dried up, I pivoted again—this time into digital marketing for law firms. I spent years at FindLaw, where I discovered a passion for content strategy and client communications. That passion eventually grew into a business: I founded a boutique marketing agency, Custom Content Solutions, which I ran for over a decade. I led a talented team, built a multi-six-figure operation, and worked with a variety of business owners and marketers across the United States and around the world.
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During that time, I also co-founded a small estate planning firm for a few years, worked for and volunteered with nonprofits in the arts and professional services sectors, and became a sought-after speaker on both big and small stages.
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That journey taught me how to lead with values, communicate with intention, and create strategies that truly support people and the goals they’re pursuing.
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Eventually, I felt the pull back to law, but on my own terms. Today, I’m proud to split my time between:
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Helping individuals, families, business owners and nonprofit leaders in Minnesota with tailored legal services
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Supporting solopreneurs, nonprofits, and small businesses with strategic marketing coaching services
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Teaching, inspiring, learning from and connecting with others through transformational event and speaking engagements
The Values That Lead the Way, No Matter the Course
Do Our North Stars Align? Let’s Chat!
Every role I’ve held—and every pivot I’ve made—has been guided by a single throughline: I care deeply about people and helping them succeed in the work they’re called to do.
Whether you're here to build a brand, protect your legacy, scale your mission, or get unstuck, you deserve a partner who listens well, thinks strategically, and walks beside you with integrity, insight and encouragement.
If that’s what you’re looking for, I think we may be a great fit for each other. ✨