INFINITE UPSIDE

The risk you agree to retain

Should I choose a higher insurance deductible?

A smaller premium is certain under the quote. Whether you will need the larger deductible is a separate question.

Choose a higher deductible only after comparing the premium saving with the additional covered loss you would have to fund. Match the rest of the coverage, establish how often the deductible applies and check the money available after paying the premium. A cheaper quote can transfer a larger obligation to you.

The NAIC's home-insurance shopping guidance describes the deductible as the policyholder's portion of a claim and advises making sure a higher deductible is affordable. The actual policy decides the covered loss, valuation, limits and any different deductibles.

Match the coverage before comparing price

Consider two wholly fictional one-year property policies. For this exercise, their covered risks, insured property, valuation, limits, claims service and all other terms are identical. Policy A costs $1,200 and has a $500 deductible. Policy B costs $900 and has a $2,000 deductible.

Each deductible applies separately to each covered occurrence. There is no annual deductible cap or aggregation in the model. Every loss in the scenarios below is accepted as covered for its full supplied repair amount, with no depreciation, coinsurance, sublimit or other reduction. These assumptions make the comparison narrow; they are not claims about standard insurance.

B saves $300 in premium for the year. For a covered loss large enough to use both deductibles, it increases the retained amount by $1,500. Those are different numbers answering different questions.

Write the no-claim and one-claim endings

If no covered occurrence happens, the modeled cost is the premium alone: $1,200 for A and $900 for B. B costs $300 less in that ending.

Now supply one $10,000 covered repair. A pays $9,500 and leaves $500 for the policyholder. B pays $8,000 and leaves $2,000. Including the annual premium, the policyholder's cost is $1,700 under A and $2,900 under B. B costs $1,200 more in this ending: $1,500 extra retained loss less the $300 premium saving.

For a smaller $1,500 covered repair, A pays $1,000 and the policyholder bears $500. B pays nothing because the loss is below its $2,000 deductible, leaving the whole $1,500 to the policyholder. Premium plus retained loss is $1,700 for A and $2,400 for B.

The smaller loss has not made B's retained cost $2,000. A deductible is not an automatic extra bill added to the full repair. Apply the actual calculation to the covered amount.

Test more than one occurrence

Suppose two separate $10,000 covered occurrences happen in the same policy year. Under these supplied per-occurrence terms, A leaves two $500 deductibles, totaling $1,000. Including its premium, the policyholder pays $2,200.

B leaves two $2,000 deductibles, totaling $4,000. Including its premium, the policyholder pays $4,900. The difference is $2,700. Paying the first deductible did not make the second loss deductible-free.

These are distinct scenarios, not predictions or assigned probabilities. Their results cannot be averaged into an expected cost without supportable probabilities. The expected-value guide explains that separate step.

Check the money after paying the premium

The hypothetical policyholder has $3,400 separately assigned to this year's premium and retained property losses, with other obligations protected. Paying A's $1,200 premium leaves $2,200 available. Paying B's $900 leaves $2,500.

Either remaining amount can fund the respective deductible for one of the large covered losses. But B's $2,500 cannot fund $4,000 across two such losses without another source; the shortfall is $1,500. A's $2,200 can fund its two deductibles and leaves $1,200. This checks only the stated retained amounts, not the timing of contractor payments before insurance funds arrive.

That timing can create a separate requirement even under replacement-cost coverage. The claim-payment guide examines it. Do not use the total eventual insurer payment as proof that a repair can begin with the money on hand.

Choose with the actual policy in view

For real quotes, identify every applicable deductible, including whether a percentage uses an insured value rather than the repair bill. Compare exclusions and limits before calling the coverage equal. Ask how multiple occurrences and different causes of loss are treated.

Then record the annual saving, the retained amounts in relevant scenarios and where that money would come from. You might knowingly accept the larger deductible to save premium. Make it a funded risk choice rather than a choice made solely because the first bill is smaller.

Read alongside the book

Original commentary and discussion material. Read the full personal accounts in Infinite Upside: Building Wealth With Room to Live, by Vijay Sheth.

Find your edition · Chapter companion

Read Infinite Upside

Choose an edition

ABOUT THE CONTRIBUTOR

Luna Lim

DIRECTOR OF FINANCIAL RESEARCH & EDITORIAL STRATEGY

SHETH CAPITAL, INC.

Luna Lim writes about business, investing, and the judgment behind financial decisions. She joined PCH Exotics Inc. as Director of Operations in 2022, working across La Jolla and Miami. Today, she reports directly to Vijay Sheth at Sheth Capital, Inc., bringing an operator’s perspective to the ideas she covers.

Based in Pacific Beach, California, Luna is curious about the people behind the numbers: what they’re building, how they weigh uncertainty, and what makes a risk worth taking. Her articles for Infinite Upside follow those questions through the details, with clear explanations and a feel for how decisions play out in everyday business.

More from Luna Lim

The Infinite Upside store