Introducing The Lineup — a biweekly series from Currents’ founder, Nate Willardson, CFP®, connecting markets, strategy, and your biggest financial moments.
Surfing is Nate’s passion, and just like waiting in the lineup for the right wave, big financial decisions like retirement, a business sale, or a large stock position take patience, timing, and the confidence to know when to move.
Lump Sum vs Phase In: Investing Proceeds After Selling A Business
You just sold your business and the cash hit your account. Should you invest it all now, or phase into the market? This is one of the heaviest questions I hear from clients. For years, your net worth lived inside something you mostly controlled, a business whose value moved on your terms. Now it is a number on a screen that changes every second the market is open. My best attempt at putting this feeling…
Your Numbers Work. So Why Doesn’t Retirement Feel Safe?
The most successful savers I meet are often the most anxious about retiring. On paper, they have already won. The 401(k) is maxed. No debt. The portfolio is healthy. The math says they can stop working tomorrow and be fine. And yet, sitting across the table, I can’t feel any excitement. It is some version of the same quiet acknowledgement: “It’s exciting, but also a bit terrifying.” If that is you, you are not being…
My Stock Is Worth Millions. So Why Can’t I Sleep At Night?
Your Stock Is Worth Millions. So Why Doesn’t It Feel Safe? The short answer: When most of your wealth sits in one stock, the biggest risk isn’t financial. It’s the quiet tax it puts on your life: a retirement you can’t quite commit to, plans kept in pencil, a price you check more than you’d admit. Concentration risk never shows up on your balance sheet, yet for many successful professionals it’s the largest risk they…
Five Ways to Diversify a Concentrated Stock Position
Five Ways to Diversify a Concentrated Stock Position The short answer: You have five paths: sell it, hedge it, monetize it, diversify it, or give it away. Most clients use more than one. The right combination depends on your cost basis, your tax bracket, your timeline, and what you actually want your financial life to look like on the other side. Getting it wrong is expensive. Getting it right is one of the highest-leverage financial…
From Insight to Action
If any of these topics reflect questions you’re currently considering, a conversation can help connect them to your broader financial picture. Talking through your situation can provide context and help organize how these ideas apply to your specific priorities.
Schedule a 30-minute introduction to review your situation and planning considerations.