My newsletter for motivated professionals who want to create meaningful change in the modern workplace — designed to help you lead with greater clarity, confidence, and authenticity.
I once worked with a brilliant strategist, let's call him Jacob. He'd risen quickly through management ranks and, by broad consensus, was destined for the executive suite. But Jacob developed a habit that ultimately burnt him out: planning obsessively for every possible outcome before making decisions.
He'd create elaborate scenarios ahead of meetings: "If they question the timeline, I'll say this... if they challenge the budget, I'll counter with that..." While our peers were progressing, Jacob was still rehearsing worst-case scenarios. The constant worry exhausted him until even routine choices became agonizing.
"What if I've made the wrong call? Did I miss something crucial?"
Sound familiar?
As a leader, you constantly have to be decisive without complete information. You launch strategies, reorganize teams, or commit resources to initiatives that might not pay off. You put something out into the world, and then? You wait.
Jacob’s peers who continued to advance shared one key trait: successful leaders make peace with not knowing everything. They don't waste energy trying to control what they can't control. Instead, they focus on what they do know: who they are, what they bring to the table, and the people they can rely on.
So how do you develop this kind of leadership confidence? Let's talk about it. Here are the strategies that work for me and other leaders who've learned to handle uncertainty without letting it derail their peace of mind.
Your network is your best defense against uncertainty.
When you're waiting for a significant outcome, your mind can become your worst enemy. If permitted to wander, it crafts elaborate disaster scenarios that feel increasingly real as time passes. What begins as "maybe they didn't like my proposal" escalates to "my entire career is in jeopardy," all while the actual situation hasn’t changed.
These mental spiral happens much more easily when you're isolated. When anxiety strikes, your instinct might be to retreat and keep your worries to yourself. Without trusted voices to provide perspective, your internal narrative goes unchallenged. You need relationships that can ground you when uncertainty has you catastrophizing.
Strong connections with the right people are your most valuable resources. They help recalibrate your thinking when it veers toward worst-case scenarios, provide expertise where you have gaps, and reinforce your confidence when it wavers. We're simply not wired to process uncertainty effectively all by ourselves.
I learned this lesson as a single parent. I had to become resourceful. Whether I needed furniture refinishers or last-minute childcare, I built connections with people who could help. These relationships thrived because I showed genuine appreciation and respect; I never waited until the last minute unless it was truly an emergency, I compensated people fairly, and I made it clear I was equally available when they needed support.
This same principle applied when I led a 30-person team at Google. I had five direct reports whose judgment I could always rely on. When I was tied up or needed support, they became my safety net, addressing issues before some might have reached crisis level. Their capabilities gave me the bandwidth to concentrate on larger strategic questions.
Digital workplaces connect us technically but can isolate us emotionally. Look beyond your screens to build intentional connections. Schedule face-to-face meetings when possible. Pick up the phone instead of sending another email. Create spaces where your team can interact informally. These are essential buffers against the anxiety that festers when we face uncertainty alone.
Be resourceful. It means accepting that you won't have all the answers yourself, but you'll know how to find them and who to turn to.
Build confidence through self-awareness.
In my years of recruiting, I've interviewed thousands of people who could meticulously list every task they'd performed, but they couldn't do the critical work of articulating how those experiences affected their skills, knowledge, and abilities, or in other words, their competencies.
Too many people operate on autopilot, drifting through careers without reflecting on their unique strengths. When you're disconnected from your own value, uncertainty can feel destabilizing. Real confidence begins with honest self-awareness. You’ve got to be able to look in the mirror and say without hesitation, "Damn, I'm good at [XYZ]." Take stock of your competencies. When you know what you bring to the table, it’s easier to navigate the unknown.
I often say to people, "Tell me your story. Don't read me your resume." The narrative you've constructed about your professional journey reveals a lot about your self-awareness. Did you make intentional choices? Do you understand how each experience built upon the last? Or are you just reciting a list of positions?
The most effective leaders know what they've accomplished and understand who they are. When these align, you develop a confidence that lets you experience waiting and uncertainty not as sources of anxiety, but as opportunities for growth.
Here’s how you can help yourself when doubt sets in.
When dealing with uncertainty, you have two options: dwell in worrying or take action. A single step in the right general direction beats endless planning in no direction at all.
The next time you feel your confidence wavering, don't just sit with it, do something. Start here:
✔ Focus on one thing at a time and prioritize. Avoid what I call “dogpiling,” where you heap everything that feels uncertain or is going wrong into one gigantic problem and become overwhelmed.
✔ Write down three things you bring to the table. Keep them on your desk or in a digital note so you have a gentle reminder of these when something triggers your self-doubt.
✔ Identify one person in your network you can lean on, and reach out. For example: Call a colleague or grab coffee with a mentor instead of overanalyzing alone.
What’s one small action you can take today? Send that message, ask for advice, move something forward. You’ve got this!
Sending love and light,
Ginny