I help women turn “What now?” into purpose in progress.
I'm Jessica Flagg. Former corporate marketing communications executive and the one who will be firmly in your corner.
You can spend years pouring yourself into your work, your family, or both, until the life you built starts to fit a little differently. Maybe you're ready to grow into a bigger leadership role. Maybe your kids need you differently now and you finally have room to think about yourself again. Or maybe you simply know there's more you want to do with your strengths, time, and energy… you're just not sure what that looks like yet.
I know that feeling because I've lived my own version of it. I spent more than twenty years leading enterprise communications, brand strategy, and U.S. and global teams, and the part of the work I loved most was always developing people. I found real joy in helping them recognize their strengths, trust their voice, and move toward what mattered.
When my position was eliminated and my corporate chapter ended, I chose to turn the development work toward myself. I had built the career, led the teams, and earned the title. And then I realized that professional accomplishment and personal confidence are not always the same thing. Looking back, I could see that some of that doubt had been with me much longer than the job. Growing up in a small town in Southwest Virginia, I had quietly wondered whether someone like me really belonged in the world I eventually built a career in. I had more than twenty years of evidence that I did, but losing the title showed me how much of my confidence had become tied to what I did and what I'd accomplished, not who I am.
A retreat gave me room to reset and reconnect with what mattered. But figuring out what I wanted was only part of it. I also needed the people who knew me well to remind me what they saw in me, help me rebuild confidence in what I brought beyond the title, and encourage me to go after what I wasn't quite ready to claim for myself yet. Having people in my corner is what moved me from reflection to action.
That experience became the foundation for Purpose in Progress.
WHAT I DO NOW
Through retreats and 1:1 coaching, I help women step away from the noise, reconnect with their strengths, values, and voice, and recognize what matters enough to act on. Then we turn that focused purpose into something real: decisions made, conversations had, goals advanced, boundaries changed, confidence built, and meaningful movement that continues as you navigate everyday life.
WHAT I BELIEVE
People over performance. Titles, roles, and circumstances change. The person and what she has to contribute are the point.
What matters should lead somewhere. Reflection earns its keep when it helps you recognize what deserves your energy and begin doing something about it.
In your corner, not on a pedestal. My job is to see, challenge, encourage, and help you keep going. It’s not to hand you a ready-made answer.
Strengths first. Most people have more capacity than they're using or claiming. I help you recognize it, trust it, and put it to work.
Progress over arrival. There's no finished version of you to reach. There's choosing what matters and moving it forward, on purpose.
If something is shifting for you too, let’s start where you are.
Jessica Flagg bio
Jessica Flagg is a former corporate communications executive and the founder of Purpose in Progress, where she leads retreats and 1:1 coaching for women entering a new chapter of work and life. After more than twenty years leading enterprise communications, brand strategy, and U.S. and global teams, Jessica built Purpose in Progress around the part of leadership that had always filled her cup most: helping people recognize their strengths, trust their voice, and move toward what matters with someone firmly in their corner. Her approach combines restoration with navigation, creating room to step outside the noise and reconnect with what matters, then turning that understanding into decisions, goals, conversations, and meaningful progress.