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When Our Journey Forward Requires Thinking Backwards
Unstuck Monthly | July 2025
A simple teaching exercise revealed why most leaders feel scattered—and the backwards approach that creates focus.
A Map Without a Destination
During my first week as a Teach For America corps member, our instructional coach, Doug, handed us a paper road map and pointed to our starting location. “Plot your route to get across this map,” he instructed. “Highlight the roads you'll take.”
The frustration was immediate. “There’s got to be a better way to do this,” someone muttered. “This is stupid. I’d never start driving my car without knowing where I was going.”
After watching us struggle for several minutes, he revealed the destination on the other side of the page. Suddenly, everything changed. We felt unburdened. With a clear endpoint, we could make strategic decisions: Take the direct route or the scenic one? Visit important landmarks along the way? Calculate fuel costs and necessary supplies?
This exercise introduced us to backward design, the teaching principle of starting with your desired outcome and working backwards to create your plan. But what struck me then, and what I see consistently with leaders today, is how many of us are trying to plot our professional ambitions without knowing our destination.
The Vision Gap
My own research confirms what that map exercise revealed: many of us struggle most with “casting a vision for the future.” In my survey of professionals across industries, this behavior scored lowest, averaging 6.9 out of 15 possible points, compared to all other critical behaviors for owning our careers on our own terms.
Source: The Self-Determination Compass Assessment, 2025
Having a clear vision for the future goes beyond best practices for career planning. It’s a prerequisite for performing now. Being exceptional today requires understanding where your role, your team, and your organization need to be heading. Without that clarity, you’re reacting to circumstances rather than driving them.
Know a teammate who might be navigating without a clear destination? This backward planning approach could be exactly what they need.
The Leadership Backward Design
This gap between activity and direction shows up consistently in my coaching work.
I recently worked with a director who felt pulled in multiple directions: managing an underperforming team member, taking on important operations duties, and trying to develop a new change management and transformation role. She was expending enormous energy, feeling stressed, nearing burnout, and losing the plotline to her own ambitions.
The breakthrough came when she clarified her destination: she wanted her VP’s role when he eventually moved up. Suddenly, every decision had a purpose.
Should she continue managing the struggling employee? Only if it built the tough conversation skills she’d need as VP.
Should she continue to lean in on operations issues? Yes, because her boss specifically said she needed broader business exposure to be promoted. And, she could lean in more effectively with her change and transformation approach, acting more as a strategic partner rather than qualified implementer.
Newfound clarity and focus on the future enabled intentional decision-making.
Your Summer Planning Opportunity
This kind of intentionality and search for clarity is exactly what summer’s quieter pace makes possible. Additional bandwidth and reduced urgency create perfect conditions for this kind of transformational leadership development. While others are coasting, you can use these weeks to:
Define your professional destination with the specificity needed for effective planning
Identify the key experiences and capabilities that will get you there
Create filters for making better decisions about opportunities and distractions
Position yourself strategically for fall planning cycles and year-end conversations
The leaders who emerge from this summer with clear vision and aligned plans will have a significant advantage as business intensity picks up again.
Who in your network could benefit from this strategic approach to summer planning?
The next time you find yourself spinning your wheels or feeling pulled in multiple directions, remember Doug's lesson: you can’t plot an effective route until you know where you're going.
The difference between leaders who thrive and those who merely survive often comes down to this: intentional direction versus reactive motion.
Thank you for sticking with me!
Until next time,
Alex
P.S. If this resonated with you, I’d love to hear about it. Reply and let me know which part hit home, or share it with someone who needs to set a clearer vision for the future.
Ready to create your professional future on your own terms?
I work with ambitious leaders who want to build the internal capacity for exceptional leadership. If you'd like to explore how backward design thinking could transform your approach, book a Q3 Leadership Check.
Great conversations start with shared insights. My coaching practice, like this newsletter, thrives on connections. If you know someone who's navigating their own sticking points, I'd love for you to share this with them.
