Adam Olson Financial Advisor CFP, LUTCF, FSCP, RICP

06/03/2026

Spending thousands on travel without the guilt of a shrinking portfolio is possible if you use a specific structural method to fund your trips. Whether you set a flat annual ceiling like 1% of your portfolio or allocate specific sums for bucket list items like an Alaska cruise or a trip to Italy, having a defined plan removes the guesswork. Psychologically, moving these funds into a separate high yield savings account labeled as your go go fund can eliminate spending guilt because you aren't pulling from retirement money, you are pulling from vacation money. You might also choose to front load your spending in your late sixties when your health is highest, or use a lifestyle flex adjustment where you only take the big upgrades when the market is up. By segregating your travel cash and giving every dollar a job, you can enjoy the return on your moments without constantly checking your account balance.

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Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

06/03/2026

Your portfolio is more than just performance numbers. Fees, taxes, risk, income planning, beneficiary designations — it all matters. Click the link to get the free checklist.

The years around retirement are when alignment matters.

06/02/2026

Adding a 20,000 dollar annual travel budget to your retirement is more than just a lifestyle choice; it is a permanent line item that significantly impacts your safe withdrawal rate. For a 1.5 million dollar portfolio, this budget alone can account for over 1.3% of your nest egg every single year, and because these are after tax dollars, your actual withdrawal from a traditional IRA could be much higher to cover federal and state taxes. In the Red Zone, a better strategy is to front load your travel spending between ages 65 and 75, your most active go go years, and then plan for a natural scale back as you transition into a slower pace of life. By modeling travel as a specific withdrawal strategy rather than a random expense, you can see the world without worrying if your portfolio is on a one way ticket to zero.

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Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

06/02/2026

06/01/2026

Skipping travel insurance to save a few hundred dollars is a dangerous gamble in the Red Zone because most retirees don't realize that original Medicare provides almost no coverage outside the U.S. A minor hospital stay in Europe or Mexico can quickly cost up to 15,000 dollars, while a major cardiac event or an emergency medevac back to the States can exceed 150,000 dollars. Even if you have a Medigap plan, it often has a lifetime limit for foreign travel that could still leave you with a massive six figure hole in your nest egg. Spending a few hundred dollars to protect a ten thousand dollar trip and a million dollar portfolio is not an extra expense; it is basic risk management. Don't let one bad slip on a cobblestone street in Italy turn your dream vacation into a financial nightmare that derails your entire plan.

Got questions? Visit my bio to book a free clarity call

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Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

05/31/2026

Choosing the right month to retire is a strategic decision governed by health, tax efficiency, and HR logistics rather than just a random date on the calendar. Retiring in the spring or summer helps you avoid the winter trap of isolation and depression, setting a positive tone for your new go go lifestyle. From a tax perspective, leaving in the first quarter creates a partial year of income that opens a golden window for Roth conversions and tax gain harvesting at significantly lower brackets. It is also vital to perform an HR deep dive to ensure you don't leave money on the table, such as vesting RSUs or unpaid bonuses that might payout shortly after your planned date. By front loading your 401(k) in those final months and timing your exit correctly, you can make the transition into retirement much smoother and more profitable.

Got questions? Visit my bio to book a free clarity call

Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

05/30/2026

Even the world's largest asset managers are now confirming that adding guaranteed lifetime income to your retirement plan can increase your sustainable spending by over 20%. The reality is that retirement should not be about managing a pile of cash, but about turning that pile into predictable income that covers your core needs like food, shelter, and healthcare. In the Red Zone Retirement Planning Process, we use guaranteed sources like Social Security and pensions for your essentials, while letting the markets fund your "wants" like travel and hobbies. This structure ensures that market downturns stop controlling your life and provides a vital shield against inflation, so your income remains predictable even as your expenses shift and grow over time.

Got questions? Visit my bio to book a free clarity call

Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

05/29/2026

In 2026, a million dollars is just a number that doesn't account for the reality of taxes, inflation, and rising healthcare costs. Since retirement is truly about income rather than assets, that million-dollar nest egg might only produce three to four thousand dollars of monthly spending power—especially if the government still owns a portion of it through pre-tax accounts. Success in the Red Zone requires a written income plan that transforms your big portfolio into predictable paychecks while incorporating lifetime tax planning to minimize what you owe. Ultimately, it’s not about how much you have, but about building an engine that generates consistent income so you never have to worry about how your lifestyle holds up over time.

Got questions? Visit my bio to book a free clarity call

Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

05/28/2026

Sequence of returns risk can wipe out your retirement faster than a stock market crash ever could because it locks in permanent losses when you are forced to sell investments during a downturn. If you start taking distributions while the market is low, you damage your portfolio’s ability to recover, often leading to a situation where two people with identical savings end up with completely different outcomes. In the Red Zone, we solve this by protecting the first decade of your retirement income—your "Go-Go" years—ensuring that your travel and leisure activities aren't held hostage by market volatility. By bulletproofing your plan against this timing risk, you can spend with confidence knowing that your long-term wealth is still compounding in the background.

Got questions? Visit my bio to book a free clarity call

Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.

05/27/2026

If you find travel more exhausting in your 60s than in your 40s, it is likely because you are still trying to travel like a 40 year old instead of investing in your comfort and energy. In the Red Zone, making strategic upgrades like choosing direct flights over long layovers and paying for pre booked transport to avoid the stress of navigating a new city can completely transform your experience. Slower itineraries that focus on two cities over two weeks rather than five cities in ten days allow you to actually see more by rushing less, especially when you build in dedicated rest days for naps and long lunches. From staying in central accommodations to avoid long commutes to securing comprehensive travel insurance as a shield against international medical bills, these adjustments are about more than just luxury; they are about protecting your health and your retirement lifestyle. By shifting your mindset from budget travel to quality experiences, you ensure that every trip provides the high return on moments you’ve worked so hard to achieve.

Got questions? Visit my bio to book a free clarity call

Visit for more - www.adamdolson.com

Contact a tax/legal advisor for tax/legal advice specific to your situation. All investing involves risk, including the possible loss of principal.