Saving Well Is Only Half the Plan
Here's the Other Half
The first half is about building. The second half is about not losing what you built to taxes, bad timing, and decisions you didn't know you had to make.
In my experience, retirement readiness isn't only about how much you've saved. It's also about the decisions you make in the 3-5 years before you retire, and many of those decisions can't be undone once you've made them.
Claiming Social Security at the wrong time isn't a minor miscalculation. For a married couple, the difference between a good strategy and a poor one could play an important role in retirement success.
Pulling from your 401(k) before your Roth or taxable accounts isn't just a matter of preference. In Oregon, with a top state income tax rate of 9.9%, the order you withdraw from your accounts can cost you or save you tens of thousands of dollars.
Retiring at 62 without a healthcare plan isn't just an oversight. It's a 3-year gap before Medicare that can run $1,000-$2,000 per person, per month , and it has to come from somewhere.
None of these are obscure edge cases. They're the decisions many Oregon pre-retirees are facing right now, often without realizing how much is riding on them.
This isn't a list of retirement tips you could find on Google
It's a self-assessment built around the specific gaps that show up often in the plans of people who think they're ready, but aren't quite there yet.
Many retirement calculators use it. Many financial articles repeat it. Question 1 shows you why the real number can be different, and how to find it.
"Claim early because you never know how long you'll live" feels logical. Question 2 walks through what the actual math looks like, and why the obvious move isn't always the right one.
Question 3 explains why, and what to think through before you pull from your largest account first.
Many people know it exists. Question 4 shows you what it actually costs and what your options are.
There's a specific type of risk that only shows up in the first few years of retirement, and it doesn't show up on a brokerage statement. Question 5 shows you how to check for it.
This Was Built For You — If You're Close Enough That These Questions Feel Real
If you're an Oregon resident between 55 and 65, have been a solid saver, and you're starting to think seriously about when and how to retire, this was built for you.
Not for people just starting out. Not for retirees who've already made these decisions. For the person who's close enough to retirement that these questions feel real, but hasn't yet had a proper roadmap for working through them.
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Takes about 10 minutes to go through. Many people find 2-3 gaps they didn't know they had.
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Garrett is a fee-only, fiduciary CFP®, which means he's legally required to act in your interest, not his. No commissions. No product sales. Just planning.
I built this checklist because the same gaps kept showing up in client conversations, people who had done everything right for 30 years, but were about to make a decision in the 18 months before retirement that would cost them far more than they realized. The checklist is my way of helping more Oregon pre-retirees catch those gaps before they become permanent.
That probably means at least one thing above landed.
Download the checklist and find out where you actually stand.
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Disclaimer
This is intended as a general educational resource to help you think through key retirement planning considerations. It is not a comprehensive financial plan or personalized investment, tax, or legal advice. The information provided is general in nature and may not apply to your specific circumstances. However, it is designed to offer useful context and highlight areas that may be worth evaluating based on your situation.
A formal advisory relationship is only established through a signed agreement. Investing involves risk, and tax strategies should be reviewed with a qualified professional. Harbor Horizon Financial, LLC is an Oregon-registered investment adviser. Registration does not imply a certain level of skill or training.