https://aspirean.com/perspectives.html Essays and commentary from Aspirean Wealth on exits, equity compensation, tax strategy, and what the evidence actually says about investing. en-us Fri, 12 Jun 2026 12:00:00 GMT https://aspirean.com/perspectives/selling-your-business-tax-planning-before-the-exit.html https://aspirean.com/perspectives/selling-your-business-tax-planning-before-the-exit.html Fri, 12 Jun 2026 12:00:00 GMT For a business owner planning a sale in the next few years, the most valuable tax strategies depend on time. https://aspirean.com/perspectives/concentrated-company-stock-how-much-is-too-much.html https://aspirean.com/perspectives/concentrated-company-stock-how-much-is-too-much.html Tue, 02 Jun 2026 12:00:00 GMT For an executive accumulating RSUs, holding vested shares is an active decision to buy. https://aspirean.com/perspectives/business-concentration-when-to-diversify.html https://aspirean.com/perspectives/business-concentration-when-to-diversify.html Thu, 21 May 2026 12:00:00 GMT For an owner whose company is the overwhelming majority of their net worth, diversification is about securing the family's baseline, not doubting the business. https://aspirean.com/perspectives/10b5-1-plans-diversifying-as-an-insider.html https://aspirean.com/perspectives/10b5-1-plans-diversifying-as-an-insider.html Thu, 07 May 2026 12:00:00 GMT For an executive with trading windows and MNPI exposure, a Rule 10b5-1 plan turns diversification into a pre-committed schedule. https://aspirean.com/perspectives/after-the-sale-making-the-proceeds-last.html https://aspirean.com/perspectives/after-the-sale-making-the-proceeds-last.html Thu, 16 Apr 2026 12:00:00 GMT For a founder who just sold, the skills that built the company are not the skills that preserve the proceeds. https://aspirean.com/perspectives/iso-exercises-and-the-amt.html https://aspirean.com/perspectives/iso-exercises-and-the-amt.html Thu, 02 Apr 2026 12:00:00 GMT For an executive holding incentive stock options, the AMT is the toll on the road to capital-gains treatment. How to size an exercise so the toll stays small. https://aspirean.com/perspectives/sudden-wealth-the-first-year.html https://aspirean.com/perspectives/sudden-wealth-the-first-year.html Thu, 12 Mar 2026 12:00:00 GMT For someone who has just inherited assets or lost the spouse who managed them, the first year divides into what is genuinely urgent and what only feels urgent. https://aspirean.com/perspectives/turning-assets-into-income.html https://aspirean.com/perspectives/turning-assets-into-income.html Wed, 18 Feb 2026 12:00:00 GMT For a family living off assets rather than earnings for the first time, income is a structure, not a product. https://aspirean.com/perspectives/taking-over-the-family-finances.html https://aspirean.com/perspectives/taking-over-the-family-finances.html Tue, 03 Feb 2026 12:00:00 GMT For the spouse who was never the one managing money, taking over is a context problem, not a competence problem. https://aspirean.com/perspectives/anchored-uncertainty.html https://aspirean.com/perspectives/anchored-uncertainty.html Thu, 04 Sep 2025 12:00:00 GMT Tariffs, the Fed and new all-time highs fill the headlines. Chris Winkler on why uncertainty is the rule, not the exception, and how a plan anchors you. https://aspirean.com/perspectives/social-security-insecurity.html https://aspirean.com/perspectives/social-security-insecurity.html Thu, 05 Jun 2025 12:00:00 GMT Worried about Social Security? Chris Winkler answers the most common fears with information drawn directly from the Social Security Administration itself. https://aspirean.com/perspectives/a-case-for-calm.html https://aspirean.com/perspectives/a-case-for-calm.html Sun, 04 May 2025 12:00:00 GMT Market uncertainty is inevitable. Often the biggest determinant of investment success is not the economy or the Fed but an investor’s own behavior. https://aspirean.com/perspectives/tariff-trepidation.html https://aspirean.com/perspectives/tariff-trepidation.html Thu, 03 Apr 2025 12:00:00 GMT When tariffs rattle markets, the impulse is to step back. Chris Winkler on why composure and staying invested have historically served investors better. https://aspirean.com/perspectives/well-that-escalated-quickly.html https://aspirean.com/perspectives/well-that-escalated-quickly.html Fri, 07 Mar 2025 12:00:00 GMT Optimism turned to unease in a month. Chris Winkler on why pessimism moves fast, why this time rarely is different, and how a plan holds when headlines do not. https://aspirean.com/perspectives/the-illusion-of-certainty-why-predictions-rarely-pay-off.html https://aspirean.com/perspectives/the-illusion-of-certainty-why-predictions-rarely-pay-off.html Wed, 22 Jan 2025 12:00:00 GMT Every January brings confident market forecasts. Chris Winkler on why predictions rarely pay off, and what investors who knew the future still got wrong. https://aspirean.com/perspectives/the-impact-of-elections.html https://aspirean.com/perspectives/the-impact-of-elections.html Fri, 01 Nov 2024 12:00:00 GMT Markets absorb political news faster than anyone can predict. Chris Winkler on why an election outcome is a poor reason to change a long-term investment plan. https://aspirean.com/perspectives/the-cost-of-living-surge-a-comparative-look-at-housing-cars-and-savings-rates-from-1970-to-2022.html https://aspirean.com/perspectives/the-cost-of-living-surge-a-comparative-look-at-housing-cars-and-savings-rates-from-1970-to-2022.html Fri, 17 May 2024 12:00:00 GMT Chris Winkler compares housing, car prices and savings rates from 1970 to 2022, and what the widening gap against median income means for planning today. https://aspirean.com/perspectives/deposits-withdrawals-the-foundation-of-abundance.html https://aspirean.com/perspectives/deposits-withdrawals-the-foundation-of-abundance.html Tue, 12 Mar 2024 12:00:00 GMT Saving more than you spend is the foundation of financial well-being. Chris Winkler on why the same deposits-and-withdrawals idea shapes health and family. https://aspirean.com/perspectives/new-year-new.html https://aspirean.com/perspectives/new-year-new.html Tue, 16 Jan 2024 12:00:00 GMT A new year brings hope and a clean slate. Chris Winkler on treating time as your scarcest resource and the questions worth asking before setting your goals. https://aspirean.com/perspectives/whats-your-true-net-worth.html https://aspirean.com/perspectives/whats-your-true-net-worth.html Tue, 16 Jan 2024 12:00:00 GMT David Booth of Dimensional Fund Advisors on why net worth is more than accounts minus debts, and why making life better for others is the measure that counts. https://aspirean.com/perspectives/embracing-uncertainty-this-holiday-season.html https://aspirean.com/perspectives/embracing-uncertainty-this-holiday-season.html Thu, 30 Nov 2023 12:00:00 GMT David Booth of Dimensional Fund Advisors on why stories about facing uncertainty in life make good holiday conversation, and what they teach about investing. https://aspirean.com/perspectives/how-to-have-meaningful-conversations-with-your-family-about-money.html https://aspirean.com/perspectives/how-to-have-meaningful-conversations-with-your-family-about-money.html Thu, 30 Nov 2023 12:00:00 GMT Money is a taboo topic in many families. Chris Winkler on how parents and adult children can start the conversation without pride or fear getting in the way. https://aspirean.com/perspectives/is-the-dollars-global-status-at-risk.html https://aspirean.com/perspectives/is-the-dollars-global-status-at-risk.html Wed, 27 Sep 2023 12:00:00 GMT Jared Kizer, CFA, of Buckingham weighs whether the U.S. dollar could lose its reserve-currency status to the yuan, and what that would mean for investors. https://aspirean.com/perspectives/the-science-of-first-world-problems.html https://aspirean.com/perspectives/the-science-of-first-world-problems.html Wed, 27 Sep 2023 12:00:00 GMT Harvard research shows that as problems shrink, we redefine smaller ones as serious. Chris Winkler on keeping perspective on how good most of us have it. https://aspirean.com/perspectives/ai-and-its-investment-implications.html https://aspirean.com/perspectives/ai-and-its-investment-implications.html Mon, 31 Jul 2023 12:00:00 GMT Wes Crill of Dimensional Fund Advisors on why the market’s aggregate intelligence outweighs any single AI tool, and what that means for how you invest. https://aspirean.com/perspectives/the-storm-before-the-calm.html https://aspirean.com/perspectives/the-storm-before-the-calm.html Mon, 31 Jul 2023 12:00:00 GMT Chris Winkler on a summer of recalibration, George Friedman’s The Storm Before the Calm, and finding objectivity when markets and work feel chaotic. https://aspirean.com/perspectives/why-the-wisdom-of-the-market-crowd-beats-ai.html https://aspirean.com/perspectives/why-the-wisdom-of-the-market-crowd-beats-ai.html Mon, 31 Jul 2023 12:00:00 GMT Can AI pick stocks? David Booth of Dimensional Fund Advisors argues the market’s aggregate intelligence, millions of buyers and sellers, is the AI to trust. https://aspirean.com/perspectives/expect-the-unexpected.html https://aspirean.com/perspectives/expect-the-unexpected.html Tue, 28 Feb 2023 12:00:00 GMT From the pandemic crash to meme stocks and inflation, recent years kept surprising investors. Chris Winkler on why a plan built for your life is the answer. https://aspirean.com/perspectives/people-have-memories-markets-dont.html https://aspirean.com/perspectives/people-have-memories-markets-dont.html Tue, 28 Feb 2023 12:00:00 GMT Markets have no memory. David Booth of Dimensional Fund Advisors on why prices reflect today and tomorrow, not last year, and why timing them is a losing game. https://aspirean.com/perspectives/the-case-for-objective-optimism.html https://aspirean.com/perspectives/the-case-for-objective-optimism.html Tue, 22 Nov 2022 12:00:00 GMT Optimism can feel out of touch when markets are erratic and prices are rising. Chris Winkler makes the case for grounding it in evidence rather than instinct. https://aspirean.com/perspectives/aspirean-more-than-a-name.html https://aspirean.com/perspectives/aspirean-more-than-a-name.html Fri, 09 Sep 2022 12:00:00 GMT How two firms became Aspirean Wealth, and why we chose an invented word built on aspire to describe the clients we serve and the way we work alongside them. https://aspirean.com/perspectives/the-important-role-a-financial-advisor-plays.html https://aspirean.com/perspectives/the-important-role-a-financial-advisor-plays.html Fri, 09 Sep 2022 12:00:00 GMT What a financial advisor does at the highest level: a trusted coach who translates the research into a plan for your goals. Paul Grace on why that role matters. https://aspirean.com/perspectives/passion-persistence-patience.html https://aspirean.com/perspectives/passion-persistence-patience.html Fri, 22 Apr 2022 12:00:00 GMT Kay Confer, CFP®, on how passion, persistence and patience shaped her path from a single-parent household to a career helping families with their money. https://aspirean.com/perspectives/the-gift-of-time.html https://aspirean.com/perspectives/the-gift-of-time.html Fri, 22 Apr 2022 12:00:00 GMT A daughter’s account of managing a parent’s dementia care through the pandemic, and what it taught about planning, caregiving and the value of time. https://aspirean.com/perspectives/the-only-goals-that-matter.html https://aspirean.com/perspectives/the-only-goals-that-matter.html Fri, 07 Jan 2022 12:00:00 GMT When it comes to financial goals, the only ones that matter are yours. Chris Winkler on why we are bad at knowing what we want, and how to find out.