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A Love Letter to Your Inner Voice
How to build a new relationship with feelings of inadequacy
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Dear Inner Voice,
We need to talk. For years, you've been my harshest critic, always ready with a "you should" or "you're not enough." Remember all those times you told me "A real leader would know this already" or "Everyone can see you're failing"?
I think it's time we worked on us.
Last month’s issue kicked off a conversation about how clarity and intentionality create leadership confidence. But what about those moments when confidence feels impossibly out of reach? When you're convinced you must be the world’s worst leader?
Those moments deserve your compassion—perhaps even your appreciation.
Why? For one thing, constantly berating yourself is a recipe for burnout. For another, how you treat yourself influences how you lead others. When you model self-compassion, you create space for your team to take risks and grow from mistakes.
So what does self-compassion look like in practice, especially when wrestling with self-doubt? Start by looking at what you’re feeling from a different angle.
Embracing the Emotional Burn
Think about the last time you had a great workout.
(Full disclosure: As someone who has to be dragged to the gym, I can't believe I'm using a fitness analogy, but stay with me here.)
Remember that burning sensation in your muscles? You could interpret that discomfort as a warning never to exercise again (like my inner voice would want me to). Or you could recognize it as a signal that you're building strength, that transformation is happening because you're pushing beyond your comfort zone.
Leadership growth requires a similar perspective.
When you step into a new executive role or take on expanded responsibilities, that feeling of being stretched, challenged, even overwhelmed—it's evidence you're building new leadership muscles.
A while back, I worked with a CEO who was wrestling with not being “enough”—not good enough, smart enough, or experienced enough for the role. Together, we confronted an important truth:
“Yes, there might be others who could be a better fit for the role. But right now, in this moment, you’re the one with the responsibilities and power to lead.
Don't abdicate that power to your insecurities.
The worst that could happen? Getting replaced—which is exactly what will happen if you let fear and insecurity freeze you up.”
Instead of berating yourself for having these feelings, try building a new relationship with them:
Where do you feel the resistance most strongly?
What are 3 experiments to try to push you out of your comfort zone?
What encouragement would you give a colleague facing similar challenges?
Practical Steps Forward
Working with the discomfort of growth requires both internal practice and external support. Here are four foundational steps to begin:
Track your progress in small ways: Instead of focusing solely on big outcomes, celebrate the small wins. Did you speak up in that first meeting of the day? Did you pause to ask a clarifying question instead of pretending to know?
Find your mirrors: Who can reflect back your growth honestly and compassionately? This might be a coach, mentor, or trusted peer.
Note how many times your inner voice speaks up in an hour. Notice what it’s telling you, then intentionally shift that voice from criticism to support.
For instance, the next time your inner critic pipes up with "I should know this already," try responding with "Thank you for trying to protect me, but you don’t need to be afraid. I'm learning this now, and that's exactly where I need to be."
Create a grounding mantra: When self-doubt creeps in, what simple truth can you return to? One of my favorites: "I'm here on purpose. I'm here with purpose."
But Jess! What if they notice I’m struggling?!
When we’re engaged in transformation work, the “never let ‘em see you sweat” mentality can get in the way. I often hear leaders downplay their struggles (or wins) with "oh, it's no big deal"—even when it very much is.
But we must be brave enough to let the “cool, calm, and collected” facade go when it no longer serves.
Instead of hiding your work, consider letting others bear witness. When team members notice your efforts to change, thank them. One leader I worked with was trying to be more connected with their colleagues. When team members commented on the leader’s efforts, the acknowledgment deepened those connections further.
Most importantly, bring key stakeholders into your journey. Whether it's your CEO or board, letting them know where you're working to grow often yields unexpected support. Think of the People leader who, rather than hiding gaps in financial acumen, shares growth goals with their CEO. Instead of being penalized for not understanding the business better, finds themselves with more opportunities for learning and exposure.
A New Love Story
This February, as cards and chocolates circulate, write yourself a love letter. Appreciate all the ways you're growing, learning, and showing up for your team—even when (especially when) it feels uncomfortable:
“Dear Inner Voice, let's start fresh!”
Time to reflect:
What's one area of leadership where you're currently feeling the emotional burn?
What are 1-2 ways you can show yourself more compassion in moments of growth?
What small win in your journey can you celebrate from this past month?
More Info
Want more resources to help reframe those feelings of fear and inadequacy?
"The Power of Believing That You Can Improve" TED Talk by Carol Dweck
"The Gifts of Imperfection,” by Brené Brown
“Imposter Syndrome Has Its Advantages” HBR article
Tell me what you think of these resources and what you would add to this list! Reply to this email or connect with me on LinkedIn to share your thoughts—I read every comment!
Keep reading, keep leading,
Jess
If you've found value in The Left-Hand Column, please share it with other leaders who might benefit.
Need help putting your leadership stumbles into perspective? Schedule a free discovery session today to unlock your potential and accelerate your journey.
For more, follow me on LinkedIn or check out my website.
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