In This Edition Of The Soulful Lens at Work: ​
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To plan or not to plan? That is the question. This week we look at how much planning is enough and how much is too much.

• SOULFUL: Some of us breathe easier with a plan, others feel alive in action. Neither is right or wrong - the magic is in knowing your preference and noticing others’.
• PRACTICAL: The right amount of planning depends on the work. Look at cost of rework, reversibility, risk of misalignment, knowability, delay, stakes, and impact. Each factor tells you how much planning is “enough.”
• THE CONNECTION: Stop fighting about who’s right. Let the work speak. Sometimes it wants careful measuring, sometimes it just wants you to cut. Listening together builds trust.
• TRY THIS: Tune each factor like a dial. If it’s cheap, reversible, low stakes, and uncertain -> bias toward speed. If it’s costly, irreversible, high stakes, and knowable -> bias toward certainty.

Hi Reader,
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The old adage “Measure twice, cut once” exemplifies conscientiousness and abhors sloppiness. But then Mark Zuckerberg famously commented “Move fast and break things.”
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Which is correct?
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If you are performing a bypass on my heart, I’d like you to measure about 11 times. But if you’re writing an email, you can just start typing with no planning at all.

Those are extreme examples, but when it comes to planning work tension arises between the planners and the doers. What’s the right amount of planning?

The two tensions at play here are:

1. Speed vs Certainty
2. Cost of Change vs Cost of Delay

We’ll take a look at these two tensions, help you strike the right balance AND even better, help you understand the position of people with opposing viewpoints; the “Doers” and the “Planners”.

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Let’s jump in and help you sort through this ongoing tension.

Soulfully ✨
​- Jardena

The Doers and the Planners

Some people just feel better, less anxious, if they have a plan and everyone knows the plan.

Some people like jumping in and getting to action.

Neither is right or wrong.

Self awareness of your preference and the preference of others is key.

And it is a PREFERENCE. Your preference may not align with the optimal level of planning.
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Think about where your preference leans. In the next section we’ll look at aligning the level of planning with the situation based on clear criteria.

How Much Planning Do We Need?

There are different factors that impact how much you need to plan. You will likely have a mix of factors so tailor your planning to address the risks and leverage bias to action on less risky factors.

1. Cost / Effort to Rework
   • How expensive is it to fix mistakes later?
   • Low cost of rework → lean toward speed and iteration.
   • High cost of rework → invest in more upfront planning.
2. One-Way vs. Two-Way Door
   • A two-way door decision is reversible (e.g., trying a new feature toggle). Mistakes are cheap, so less planning is fine.
   • A one-way door decision locks you in (e.g., migrating all customer data to a new system, laying concrete). Here, more diligence is warranted.
3. Risk of Misalignment
   • If multiple people or teams are involved, lack of planning can create costly confusion, rework, or even wasted parallel efforts.
   • The more stakeholders and dependencies, the more clarity and alignment you need upfront.
4. Knowability of the Problem
   • Some domains are inherently uncertain (e.g., customer behavior, scientific exploration). No amount of planning can reveal the answers — only testing can.
   • If the situation can be fully mapped (e.g., compliance rules, physical laws), upfront planning pays off.
5. Cost of Delay (Opportunity Lost)
   • Time spent planning delays action. In fast-moving or competitive environments, waiting may be more expensive than moving forward with imperfect information.
6. Safety, Legal, or Ethical Stakes
   • When human safety, regulatory compliance, or irreversible ethical consequences are involved, the bar for planning should be higher.
7. Scale and Visibility of Impact
   • A small decision affecting a local process may need little planning. A decision affecting thousands of customers or employees should be handled with greater care.

Mix and match these factors. If safety is an issue, focus planning on safety. If cost of delay is an issue, focus on minimally viable product.

What are you planning now that could use more or less planning time?

Let the Work Speak to You

We often make planning about ourselves. Planners feel safer with a map. Doers feel safer in motion. It’s human — we each have a comfort zone. But the truth is, the work doesn’t care about your comfort zone. The work has its own voice, if we’re willing to listen.

Some work says, “Slow down, measure carefully, I’m delicate.” Other work says, “Just start, I’ll teach you as you go.” The art is in tuning in.

That’s where the practical factors come in. Instead of asking “Do I prefer to plan?” or “Do I prefer to jump in?” we can ask, “What is the work asking of us right now?” Does this decision want more certainty because the cost of rework is high? Is it a one-way door that needs care, or a two-way door that welcomes experimentation? Will confusion from misalignment create risk, or is this simple enough to just try? Can the answers even be known in advance, or do we have to learn by doing?

When we listen this way, something shifts. Planners notice the moments when the work is begging for speed. Doers notice the moments when the work is whispering, “Take your time.” The argument stops being about personal style and starts being about service to the work.

So let the work speak to you. Sometimes it says, “Measure eleven times.” Sometimes it says, “Stop fussing and just cut.” Our job isn’t to impose our preference - it’s to listen closely, and respond with care.

Try this:

When you feel stuck between “we need a plan” and “we just need to start,” break the decision down using the heuristic. Don’t treat it as one big choice — look at each factor separately and let that guide the right amount of each type of planning.

Ask these questions one by one:

1. Cost to rework
   • If rework is cheap, you don’t need to plan much here.
   • If rework is expensive, plan more carefully to avoid waste.
2. Reversibility
   • If this is a two-way door, you can move faster.
   • If this is a one-way door, take extra care.
3. Risk of misalignment
   • If a little confusion won’t hurt, you can skip heavy alignment.
   • If misalignment creates big risk or wasted effort, invest in clarity.
4. Knowability
   • If the answer is unknowable until you try, lean toward action.
   • If the answer is knowable, plan enough to capture it.
5. Cost of delay
   • If waiting costs you opportunity, shorten the planning cycle.
   • If waiting doesn’t hurt much, you can afford more planning.
6. Safety, legal, or ethical stakes
   • If none are involved, you can relax.
   • If they are involved, slow down and be thorough.
7. Scale and visibility of impact
   • If impact is local and small, go lighter.
   • If impact is wide and visible, raise the bar.

Pulling it together

Often, the answers will not all point in the same direction. That’s okay - it means you don’t need the same level of planning for every aspect. For example:

• If the decision is hard to reverse but low stakes, you might only plan enough to reduce risk of wasted effort - not a full-blown project plan.
• If it’s cheap to change but highly knowable, you might take the time to capture what you already know, then move quickly into action.

Treat each factor like a dial rather than an on/off switch. The mix of dials tells you how much planning is “enough” in this moment.

In practice: instead of arguing “we need more planning” or “we need less,” you can say, “It’s high impact and hard to reverse, so let’s slow down a little. But since rework is cheap and delay is costly, let’s also set a short planning window and then act.”