Design Your Future
An intimate group coaching program for experienced designers to explore career expansion and identity evolution.
Program overview
As an experienced designer, you can sense you’re on the cusp of great change.
Your industry is transitioning to becoming AI-first, raising questions about not only your current job but also the future of the entire field to which you’ve committed your career.
Roles are being redefined and merged. Designers are expected to “know AI” but what that means is unclear. There’s pressure to stay relevant and reinvent while still executing day-to-day work.
This is on top of the routine expectations that come with being a high-performing designer in tech.
There’s a temptation to make these things a problem. To throw up your hands or react in frustration and fear.
Design Your Future is an invitation to take a different path—to see the current moment as an opportunity to intentionally create the next chapter of your design career.
Together—through dialog, collaboration, and coaching—we’ll explore the deeper questions facing designers:
What does “designer” mean in an AI-first world—and who do I want to be within it?
How do I stay valuable when roles are blurring and expectations are constantly shifting?
What’s my relationship to craft now that speed and automation are top priorities?
How do I lead and influence in an environment that’s shrinking, stretched, or unstable?
What do I do with the quiet feeling that I’ve plateaued?
How can I make space for vision when I’m drowning in meetings, Slack messages, and mental noise?
How do I truly want my next chapter to look—and what might I need to let go of to move toward it?
Design Your Future is a dedicated space to examine these questions (and others) within a small, curated community.
Program details
Design Your Future is a six-month group coaching program. It will run from October 2025 through March 2026.
The group is limited to 12 participants to allow for personalized attention and in-depth conversations.
The program includes:
12 group coaching calls (90 minutes, every other week)
2 individual coaching sessions (90 minutes)
1 private Slack channel for async coaching support and community connection
The program fee is $2,500.
Call schedule
Group coaching calls will be held on Zoom, on Tuesdays from 12:00-1:30pm ET, on these dates:*
October 7, 2025
October 21, 2025
November 4, 2025
November 18, 2025
December 2, 2025
December 16, 2025
January 13, 2026
January 27, 2026
February 10, 2026
February 24, 2026
March 3, 2026
March 17, 2026
*Live participation is required for at least 8 out of 12 calls. Recordings will be available for all calls.
Who is this program for?
Design Your Future is for experienced product designers, content designers, and brand designers. This probably means you have “senior,” “manager,” or “director” in your title but it’s not a requirement.
It is required that you’ve worked in a design role at a tech company or digital agency for at least 5 years.
This requirement helps keep the content and conversations shared inside the group relevant for all members.
Design Your Future is best suited for designers who identify as seekers, who are interested in exploring deeper questions surrounding career expansion and identity evolution.
The program will be most rewarding for designers who are open to questioning the status quo, considering new perspectives, and experimenting with new actions.
In my experience, the power of group coaching lies in the willingness and engagement of the individuals who make up the group. Each member has the potential to amplify or dampen the effect.
The more of yourself you bring to the experience, the more you—and everyone—will get out it.
Meet your coach
Sara Calabro is a life and leadership coach who works with designers, executives, and founders. She’s been supporting people in transition for over 15 years.
As an acupuncturist, Sara helped her patients move through physical and emotional stuckness. As a creative leader, she helped her teams shift into greater responsibility and reward.
As a coach, Sara helps her clients shed their default patterns and stories so they can create the personal and professional lives they yearn for.
Before coaching, Sara worked as a senior content designer at Comcast, SimplePractice, and Brex. She also founded Just Copy, the first subscription content-design agency.
Sara is passionate about helping the design community navigate the transition to becoming AI-first.
How to apply for the next cohort
Design Your Future is limited to 12 designers. The group is intentionally kept small to allow for personalized attention and in-depth conversations about meaningful topics.