The 2026 Anti-Entrenchment Self-Audit Checklist

No matter how far you advance in your coaching or writing career, your longevity is a byproduct of your ability to adapt and reinvent yourself. 

This reinvention process is not likely to happen by accident. Given that the shelf-life of an idea is about as long as a TikTok trend, now is a good time to ask yourself some hard questions about how you’ll move forward this year.

At the current pace of innovation, one year of “business-as-usual” will put you 3-5 years behind. Here are 10 ways to avoid that.

Process Rebuild Test

• Could I redesign my entire client workflow today?
• Which steps would survive? Which would mysteriously “forget” to show up?

Empathy Flip

• If I were the job seeker, which part of my own advice would I roll my eyes at?
• Where am I coaching from convenience instead of insight?

Sacred-Cow Inspection

• What “best practices” do I treat like gospel?
• What would happen if one of them were proven wrong tomorrow?

Fresh-Eyes Comparison

• How would a digitally native résumé writer solve this problem?
• What tools or approaches would they use that I’ve never touched?

Services Survival Game

• If I could keep only three services, which earn their spot?
• Which ones am I offering out of habit or fear of change?

Bias & Avoidance Check

• What client types or industries do I quietly avoid?
• If I coached them anyway, what new expertise would I gain?

Annoying Feedback Review

• What client complaints or suggestions have I dismissed?
• Which of those are actually early-warning signals?

Alien Client Drill

• Can I coach someone with a background that feels “alien” to me?
• What assumptions do I carry into unfamiliar industries?

AI Replacement Reality Check

• If a very shiny AI replaced me tomorrow, what would my clients miss most?
• How can I double down on that human advantage now?

Belief Refresh Cycle

• What career or résumé belief changed for me in the last five years?
• Which of my current beliefs is starting to wobble?