Size the Prize — The Back-of-Envelope Math That Ranks Opportunities
Most people chase opportunities that look exciting. Smart operators do 2 minutes of math first. Expected value = (size of win if you win) × (% chance you win). Do this for 3 options and one stands out as obviously bigger. Then you spend your protected deep-work time on that.
The idea
Expected value is simple: (size of win) × (chance of winning) = how much your effort is worth. A project worth ₹10 lakh with a 50% win rate has an EV of ₹5 lakh. A project worth ₹50K with a 90% win rate has an EV of ₹45K. The second *feels* safer but the first has bigger expected value. Most people skip the math and follow their instinct ("that sounds cool"), which is why they spend time on shiny distractions instead of the actual biggest prize. Two minutes of back-of-envelope sizing on your top 3 opportunities surfaces the real winner. Then you stop negotiating and go all-in.
Who is this for?
Divya Patel
Founder · Ahmedabad
Divya juggled three opportunities: startup (20% chance), freelance (₹2L, 95% certain), partnership (₹50L, 5% chance).
The math: Startup EV = ₹16L. Freelance = ₹1.9L. Partnership = ₹2.5L. Startup won.
She went all-in (freelance = cash flow). Nine months later, it closed at ₹1.5 crore. Math wins.
"I was chasing the freelance because it felt safe. The math showed the startup was actually bigger. One number changed everything."
What you'll get
One set of 3 opportunities, sized
Three real options, each with a rough estimate of size and win chance.
Expected value calculated
(Size) × (Chance) for each — a number that ranks them fairly.
The real biggest prize, identified
Not the shiniest or most fun, but the one with highest expected impact.
Deep work aimed at the right target
You stop diluting effort across small wins and go all-in on the biggest prize.
Watch
ByteByteGo · estimation · ~8 min
Do the challenge
1List 3 real opportunities you're considering
Three things you could spend time on next: new project, new client, new direction, new market. They need to be real options you're actually weighing, not vague ideas.
💡 If you don't have 3 real options, you're not actually choosing — you're just rationalizing what you already decided. Come back when you have real choices.
2Estimate the size of each win
If each worked perfectly, what would it be worth? Revenue, users, career impact, whatever metric matters. Don't overthink it — rough is fine. ₹1 crore, ₹20L, ₹5K — ballpark.
3Estimate your win chance
What's the real % chance you win this? Not optimistic, not pessimistic — your honest read. The sure-thing freelance project: 95%. The speculative startup: 20%. Be honest, even if it's low.
💡 Help me rank 3 opportunities by expected value. For each: Opportunity: [name]. Size if you win: [revenue/impact]. Your win chance: [%]. Calculate EV = size × win chance for each, rank them, and tell me which one has the highest expected value. Then ask: does this match your gut, or does the math surface something you'd missed?
4Calculate EV and pick the winner
Expected Value = (Size) × (Win Chance) for each. ₹80L × 20% = ₹16L. ₹2L × 95% = ₹1.9L. ₹50L × 5% = ₹2.5L. The winner: ₹16L expected value. Go all-in.
Your template
SIZE THE PRIZE — Back-of-Envelope Sizing OPP. 1: ________________ Size if you win: ₹__________ Win chance (%): ___% EV = _______ × _____ = ₹__________ OPP. 2: ________________ Size if you win: ₹__________ Win chance (%): ___% EV = _______ × _____ = ₹__________ OPP. 3: ________________ Size if you win: ₹__________ Win chance (%): ___% EV = _______ × _____ = ₹__________ RANKING (highest to lowest EV): 1️⃣ ________________ EV: ₹__________ 2️⃣ ________________ EV: ₹__________ 3️⃣ ________________ EV: ₹__________ GUT CHECK: Does the ranking match your instinct? □ Yes □ No If no, what's the math missing? _____________ DECISION: Go all-in on #1. Next step: __________________________
Knowledge Check
5 quick questions to make sure the main ideas landed.
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Share the challenge — streaks are more fun together.
Tomorrow
Ask a Better Question — The One That Unlocks the Real Answer
Before you commit to an opportunity, you need honest input. But most questions are shallow and get shallow answers. A better question is open (not yes/no), specific (not vague), and curious (not leading). That one question unlocks the truth.
