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  • Writer's pictureAce Woods


This week we are sharing a retirement checklist courtesy of our favorite local Santa Cruz wealth advisors over at Harborlight Investments! HarborLight Investments, is a comprehensive financial planning and personalized investment management firm serving individuals and families. Founders Chris Sheehy and Jason Draut left their hectic jobs on the trading room floors of Wall Street to put their financial knowledge to work for regular people like you and me. They currently manage close to $100M. What we love about Chris and the Harborlight team:

  • Getting to work directly with your own LOCAL professional wealth manager

  • Having your investments managed in-house with zero outsourcing

  • Partnering with a fee-only, fiduciary team that puts you first - always

  • The peace of mind that comes when working with Certified Financial Planner™ professionals

  • Working with a team that takes a comprehensive look at your finances including your real estate portfolio and goals

Chris has passed along a helpful checklist of steps he believes everyone should consider during their pre-retirement years. Use this list to gauge your retirement readiness and reach out to Chris for a one-on-one consultation!

7 Important Steps for Financial Security

1. Identify post-retirement goals - and their financial implications.

One of the most crucial steps in retirement planning is to map out your post-retirement goals. Where do you want to live? Will you be retiring in Santa Cruz County or moving out of state? How do you want to spend your time? Will you work a side job, travel extensively, volunteer regularly, or retire entirely? The answers to these questions can significantly impact the timing and cost of your retirement.

2. Review your Social Security benefits and pensions.

It's essential to be well-informed about your Social Security benefits and pension options. Knowing what to expect in terms of dollars and sense and understanding your pension can be instrumental in your retirement planning. For Social Security, use this quick calculator to get an estimate of your benefits or, better yet, verify your eligibility, earnings, and expected payments here.

3. Plan for long-term debt.

Ideally, you’ll be debt-free by the time you retire. If you happen to have a mortgage or other long-term debt, you’ll need a strategy for managing those financial obligations in retirement.

4. Get comfortable with Medicare.

Medicare is federal health insurance for people 65 and older. As healthcare expenses increase in retirement, you will need to know how Medicare will support your healthcare needs. Start by reading over when to enroll, what it covers, and whether you may need additional coverage (Medigap). Now is also the time to research long-term care insurance.

5. Decide what to do with your 401(k).

Pre-retirement is the best time to determine what to do with an employer-sponsored 401(k). Typically, you can roll it into an IRA, keep it in the current plan, or consider other options. Remember, if you leave your job the year you turn 55, you may be able to start penalty-free withdrawals. However, if you roll 401(k) funds over to an IRA, you will be required to wait until 59 ½ to avoid the 10% early withdrawal penalty. However, you’ll still owe income tax on each distribution from a traditional 401(k). If you're close to reaching these ages or thinking about retiring at 55 or soon thereafter, Harborlight would be happy to discuss your 401(k) options available to you.

6. Consider tax planning strategies such as Roth conversions.

If your modified adjusted gross income (MAGI) reaches or surpasses specific thresholds in 2023, such as $153,000 for single filers and $228,000 for married couples filing jointly, you’re ineligible to make contributions to a Roth IRA. However, there is a solution available: the Roth IRA conversion. A Roth conversion allows you to convert all or part of your traditional IRA assets into a Roth IRA, regardless of your income level. Although you’ll pay income taxes on any converted funds in the conversion year, it makes sense if you anticipate your tax bracket being higher in retirement. If you have questions about whether a Roth conversion is right for you, reach out to Harborlight.

7. Recalibrate investments as needed.

As you near retirement, it’s smart to reassess your retirement timeline, goals, and risk tolerance with a trusted financial planner. It’s likely your willingness and capacity to take on risk may change as you get closer to retirement. A financial planner can talk through your goals and recalibrate your investments accordingly. _________________________ If you’d like to talk more about what it would look like to partner with the Harborlight team or have questions about your retirement readiness, call the office, or book a complimentary call with Chris or Jason by clicking here. You can also email chris at or call him at (831) 291 3843.


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