The Art of Getting Out of Your Own Way

Do you ever feel like you’re improvising your way through customer success? If so, you’re not alone. I had an energizing conversation with another customer success leader today, and we realized how much we didn’t know when we were thrust into our careers. We had to learn through painful experiences until we tapped into the amazing CS network that exists. That’s when our growth accelerated.

It’s not talked about enough: customer success is a multifaceted role. Responsibilities vary widely, making it even harder to learn the ropes. Many CS professionals quietly struggle with imposter syndrome, myself included. My turning point came when I embraced imperfection and learned to forge ahead with only 50-60% of the answers.

Before that, here’s what held me back:

• Doubting myself and not trusting my intuition.
• Wasting hours chasing the “perfect” solution.
• Overthinking instead of engaging with customers, my team, or leadership.
• Scrambling to fix everything, often aimlessly.
• Hesitating to ask for help.

It was exhausting and it hurt my performance, my relationships, and my reputation. My leadership, teammates, and customers were left in the lurch. Silence and uncertainty replaced the confidence I should have projected.

Turning Things Around After some tough love and a lot of learning, here’s how I made the leap:

• I bet on myself and trusted the instincts I’d spent 10 years sharpening.
• I got comfortable working with 60% of a solution—then refined it to 80% and collaborated with my team and customers to reach 100%.
• I prioritized speed of execution: less overthinking, more action. Progress beats perfection.
• I focused on my health and well-being, faced my fears, and adopted a fail-forward mindset.
• I asked for help. A lot. And guess what? I wasn’t met with annoyance or rejection—only support, fresh ideas, and stronger relationships.

My Advice to you if this sounds all relatable:

1. Get comfortable with being uncomfortable.
2. Prioritize your mental health and well-being. You can’t pour from an empty cup.
3. Act quickly but execute with the end in mind. Progress builds momentum.
4. Ask for help. Fear and hesitation are career killers.
5. Remember: You’re not alone. We’re all figuring it out. The question is: Will you do it alone or with a village?

How do you get in your own way? How do you get out of your own way?