As a productivity coach certified in Positive Psychology and Stress Management, I’ve had the honor of working with countless multi-passionate entrepreneurs. But every now and then, a coaching session distills the essence of what I do. My recent strategy call with Naomi Lerman, a certified trauma-informed mindset coach, was one of those times. It was a raw, honest look at the struggle many high achievers face: the disconnect between their incredible capacity to serve others and their crippling internal critique that tells them they are never enough.
Naomi’s story is a powerful example of why I created the Positively Living Podcast. She is a woman who passionately runs her purpose-led business, Victory Dance Coaching, helping women heal joyfully without reliving past trauma. She is also a wife and a mom to three young boys, ages eight, six, and two. If your first thought is, “Wow, she must be exhausted,” you are correct. But her biggest struggle wasn’t lack of time; it was lack of self-worth at the end of the day.
She articulated the pain point so clearly: “I think the biggest piece is setting up a schedule where I get to the end of the day, and I’m not questioning my worth.” That statement resonated with me instantly, and I know it resonated with every listener. We can achieve goals, hit milestones, and serve clients beautifully, but if we collapse into bed thinking, “I’m stupid. Why can’t I just do that?” then all the outward success means nothing.
To help Naomi, we had to step back and conduct a high-level assessment—the Clarity Call process that uncovers the hidden drivers, strengths, and personality traits dictating how a person responds to the world. We weren’t looking for a new to-do list; we were looking for meaning.
Understanding the Creative’s Paradox
We found powerful clues in her assessments. First, her highest character strengths were clearly rooted in meaning and creativity. I recognized immediately that her driver wouldn’t be efficiency for efficiency’s sake. If she struggled to stick to a schedule, it wasn’t because she was rebellious; it was because the schedule itself felt dull and lacked purpose.
I shared with her that this is the creative’s paradox: discipline is my freedom. She, like many creatives, initially felt “allergic to schedules.” But we reframed scheduling not as a cage of rigidity, but as a container for her creativity. When she infuses meaning into her schedule, her Questioner tendency (which needs internal conviction to act) is satisfied. Scheduling becomes a gift that helps her regulate and align her life.
The Season of Life and the Capacity Shift
One of the hardest topics we tackled was acknowledging her season of life. With three young boys, she is in a demanding period that simply dictates a finite capacity. Yet, she felt that acknowledging this reality was just “an excuse” to do less. This self-criticism, common among high achievers who see every minute as valuable, actually leads to freeze points and burnout.
You cannot hate yourself into a version of yourself that you love.
We shifted her perspective away from the 24-hour day and the constant pressure of context switching. Her old windows for work were too small, leading to the self-condemnation she desperately wanted to escape.
My strategy for her involved a significant capacity shift: extending her view of time from days and weeks to months and quarters. If she has Project A and Project B competing for her limited work time, she doesn’t have to choose one over the other in a week. She can alternate them. She can schedule Project A for the first and third weeks of the month, and Project B for the second and fourth. This eliminates the guilt and the daily context switching struggle, because the work is intentionally delayed, not forgotten. It’s how she increases her capacity without adding a single minute to her workday.
Bookending Your Tasks and Closing the Day
Naomi’s struggle with context switching and decision fatigue was also rooted in a lack of proper transition time. She, like many of my clients, was rushing from one task or client call right into the next, which resulted in a terrible sense of being perpetually behind.
We redefined what a “task” is. A client call is not one hour; it is an hour and a half. It includes 15 minutes of preparation time before the call and 15 minutes of processing time after the call to write notes and send follow ups while the energy and details are fresh. This is the Bookending Strategy, and it ensures the task is fully completed, providing a feeling of accomplishment and avoiding the stressful buildup of unfinished business.
Finally, we addressed her overwhelmed mornings. Her day started with a feeling of dread because the previous day’s chaos had bled into the night. The fix is deceptively simple: The Intentional Closeout.
This two part routine takes only five minutes. First, she clears her physical workspace, providing a necessary psychological close to the workday. Second, she uses a dedicated notebook to write a simple bookmark: where she left off and what she is most excited to tackle first in the morning. That simple act shifts the mental monologue from “I didn’t get to that” to “I know exactly where I’m starting.”
Naomi walked away feeling excited, inspired, and, most importantly, equipped with systems that honor who she is. If you are struggling with overwhelm, remember this: your highest efficiency will not come from a new tool, but from deep self awareness. Start by acknowledging the season you’re in, redefining your capacity, and connecting your daily tasks to the meaning that drives you. You deserve to end your day feeling accomplished, aligned, and entirely worth the life you are working so hard to build.
