Turn every stubborn 'should' into a smarter detour
The startup’s roadmap had a bold arrow pointing to Q2. “We must launch,” the CEO kept saying. Underneath the slogan lived a quieter fear—running out of money and losing credibility. The team sprinted, then stalled. Vendors slipped, an integration broke, and tension spread. A senior PM asked a different question: “What if the obstacle is a detour, not a dead end?”
They listed their shoulds on a whiteboard: launch by Q2, target enterprise only, include all three modules. Each line had a fear behind it. Status, sunk costs, investor optics. Then they designed a low‑risk alternative, a two‑week beta for mid‑market users with one finished module. Guardrails were clear: 20 accounts, feedback loops, and a public story that framed this as a learning sprint, not failure.
The micro‑anecdote came fast. The beta surfaced a workflow no one had considered that made onboarding half as long. One customer said, “We’d pay for this alone.” The team laughed in the war room with bad coffee and better news. The Q2 arrow was still on the wall, but it no longer drove them.
They briefed investors with data instead of apologies. The fear didn’t vanish, but it quieted. The roadmap changed shape. What had felt like breaking a rule felt more like choosing a smarter game.
From a behavioral lens, rigid shoulds often mask loss aversion and identity protection. Reframing obstacles as detours widens perceived choice. Designing low‑risk tests satisfies need for progress while reducing risk exposure. The result is learning velocity, not just movement. That’s what keeps companies, and people, alive.
Write the three rules you’ve been serving and ask what fear keeps each alive. Then pick one, just one, and design a tiny test that breaks it safely—a beta, a coffee with someone outside your type, a pilot with one module instead of three. Run it for a short, clear window and pay attention to what surprised you in a good way. Let those unexpected gains, not the old rule, shape your next step. Put a 30‑minute block on your calendar to draft the test today.
What You'll Achieve
Internally, less fear‑driven rigidity and more curiosity. Externally, faster learning, better timing, and options that weren’t visible under the old rule.
Trade shoulds for surrendered experiments
List your top three shoulds
Write the rules that box you in, like “I should be with X type of person” or “We must launch by Q2.”
Name the fear behind each should
Ask, “What am I afraid will happen if I release this?” Often it’s status loss, uncertainty, or disappointing someone.
Run a low‑risk alternative
Test one option that contradicts the should, with clear guardrails. Example: pilot a different segment for two weeks.
Look for unexpected gains
Capture benefits you couldn’t see from inside the rule. Let surprising wins inform your next iteration.
Reflection Questions
- Which should is costing me the most energy right now?
- What tiny test would safely contradict it?
- What data would convince me to retire that rule?
Personalization Tips
- Dating: Pause the checklist and go on one value‑aligned date outside your usual type with honest curiosity.
- Product: If “we must launch by Q2” is stuck, run a two‑week beta with 20 users to learn what the full launch wouldn’t.
The Universe Has Your Back: Transform Fear to Faith
Ready to Take Action?
Get the Mentorist app and turn insights like these into daily habits.