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When Olympic cross-country skiing champion Jessie Diggins announces retirement following the 2025-26 season, it marks the end of an extraordinary career that redefined American Nordic skiing. But her announcement also offers valuable lessons for anyone planning their own retirement transition—whether you’re an elite athlete facing a career change in your early 30s or a traditional worker approaching your 60s.
Diggins’ strategic approach to timing her retirement, planning for life after competition, and transitioning to coaching demonstrates the kind of thoughtful preparation that makes any retirement successful. Let’s explore what we can learn from her decision and how it applies to your own retirement planning journey.
The Art of Timing Your Retirement Announcement
When Jessie Diggins announces retirement with a full season’s notice, she’s demonstrating something financial advisors always recommend: giving yourself time to prepare mentally and financially for the transition. This isn’t a sudden decision made in frustration after a bad race—it’s a calculated choice that allows for proper planning.
In traditional retirement planning, this translates to what I call the “soft landing” approach. Rather than working at full capacity until the day you retire, successful retirees often begin scaling back responsibilities, training successors, and mentally preparing for the change months or even years in advance. Social Security planning works the same way—you need time to understand your options and make informed decisions about when to claim benefits.
Learning from Athletic Career Transitions
What’s particularly interesting about Diggins’ situation is that she’s retiring at the peak of her career, not because of injury or declining performance. This mirrors the experience of many successful professionals who choose to retire while they’re still performing well, rather than waiting until they’re forced out by circumstances.
The financial implications are significant. Athletes like Diggins often face unique retirement challenges—shorter earning windows, irregular income streams, and the need to completely reinvent their professional identity. These challenges aren’t unlike those faced by entrepreneurs, commissioned salespeople, or anyone with variable income who needs to plan for a more traditional retirement structure.
Diggins’s Historic Career By the Numbers
Career Statistics
| Category | Details |
|---|---|
| World Cup | 358 starts, 79 podiums, 29 victories |
| Olympics | 3 Games (2014, 2018, 2022), 16 starts, 3 medals |
| World Championships | 8 championships, 34 starts, 7 medals |
| Age at Retirement | 34 years old |
| Professional Career | 15 years (2011-2026) |
Historic Achievements & Records
| Record/Achievement | Details |
|---|---|
| Olympic Gold | First American cross country Olympic gold (2018, team sprint with Kikkan Randall) |
| Individual Olympic Medal | First American individual sprint medal (2022, bronze) |
| World Championship Gold | First American individual gold (2023, 10k skate, Slovenia) |
| Overall FIS Crystal Globe | Three victories (2021, 2023, 2025) – only non-European winner |
| Tour de Ski | First American to win overall trophy (2021, 2024) |
| Holmenkollen Medal | First American recipient (2024) |
| Distance Crystal Globes | Three victories |
Final Season Schedule
| Event | Date/Location |
|---|---|
| Season Start | November 28, 2025 – Ruka, Finland |
| Olympics | Milano Cortina 2026 |
| Career Finale | March 19-22, 2026 – Lake Placid Finals, NY |
| Final Races | Skate sprint, 10k classic, 20k skate |
Key Partnerships & Impact
| Category | Details |
|---|---|
| Coach/Wax Technician | Jason Cork (16 seasons together) |
| Advocacy Organizations | Share Winter, Protect Our Winters, Emily Program |
| Focus Areas | Mental health awareness, eating disorders, climate change, youth winter sports |
| Hometown | Afton, Minnesota |
This retirement announcement marks the end of an era for American cross country skiing, with Diggins concluding her career as the most decorated U.S. skier in the sport’s history.
Building Multiple Income Streams for Retirement
Throughout her career, Diggins has wisely diversified beyond just prize money and sponsorships. She’s built a platform through social media, written a book, and positioned herself for coaching opportunities. This diversification strategy is exactly what retirement planners recommend for anyone approaching their golden years.
Most successful retirees don’t rely on a single income source. Instead, they build what we call the “three-legged stool” of retirement income: employer-sponsored retirement plans (like 401(k)s), personal savings and investments, and Social Security benefits. Some add a fourth leg through part-time work or consulting in their former field—much like Diggins’ transition to coaching.
“The most successful retirements I’ve seen involve people who start planning their next chapter while they’re still writing their current one.”
— Michael Chen, Certified Financial Planner
For traditional workers, this might mean developing consulting relationships with former employers, exploring part-time opportunities in your field, or even pursuing passion projects that could generate income. The key is starting these conversations and explorations before you actually need the income.
Healthcare Considerations in Retirement
Elite athletes face unique healthcare needs in retirement, often dealing with the long-term effects of their training and competition. Similarly, all retirees need to plan for healthcare costs that can significantly impact their retirement budgets. Medicare planning becomes crucial for anyone approaching 65, and understanding supplemental insurance options can prevent financial surprises.
The average 65-year-old couple will spend approximately $300,000 on healthcare costs throughout retirement, according to recent studies. This makes healthcare planning as important as investment planning for most retirees. Like Diggins planning for her post-competition physical needs, you need to anticipate and budget for your healthcare requirements.
The Psychology of Retirement Transitions
When Jessie Diggins announces retirement, she’s not just ending a career—she’s transitioning from an identity that’s defined her entire adult life. This psychological aspect of retirement is often overlooked in financial planning, but it’s crucial for long-term happiness and success.
Many retirees struggle with the loss of professional identity, daily structure, and social connections that work provides. Successful retirement planning addresses these emotional and psychological needs alongside the financial ones. Diggins’ move into coaching provides her with continued purpose, structure, and connection to the sport she loves—a model worth emulating.
Creating Structure and Purpose in Retirement
The most satisfied retirees I work with have found ways to maintain structure and purpose in their lives. This might involve:
- Volunteer work with organizations that align with their values
- Part-time consulting or mentoring in their former field
- Pursuing education or skills they never had time to develop during their working years
- Starting small businesses or creative projects
- Taking on caregiving responsibilities for family members
Like other high-profile retirement transitions we’ve seen, from professional athletes to entertainment figures, the most successful transitions involve finding new ways to contribute and stay engaged rather than simply stopping work entirely.
Financial Lessons from Athletic Retirement
Professional athletes often compress their entire earning careers into 10-15 years, making their financial planning challenges similar to those faced by anyone with a shortened earning window. The strategies that work for them can benefit traditional retirees too.
First, maximize earnings during peak years. For athletes, this means negotiating the best possible contracts and sponsorship deals. For traditional workers, it means maximizing contributions to retirement accounts during your highest earning years, typically your 50s and early 60s. If you’re 50 or older, take advantage of catch-up contributions that allow you to contribute extra to your 401(k) and IRA accounts.
Second, live below your means consistently. Athletes who maintain modest lifestyles relative to their earnings often transition more successfully to post-career life. The same principle applies to pre-retirees—maintaining a lifestyle that’s sustainable on retirement income makes the transition much smoother.
Investment Strategies for Shorter Earning Windows
When you have a compressed earning timeline, whether due to athletic career length or late start in retirement savings, your investment approach needs to be more strategic. This often means:
- Higher savings rates during earning years (20-25% of income rather than the standard 10-15%)
- More aggressive investment allocations while you’re earning (higher stock percentages)
- Gradual transition to more conservative investments as retirement approaches
- Planning for potentially longer retirement periods due to early career endings
This approach has helped many professionals who, like athletes considering retirement, need to maximize their financial preparation in a limited timeframe.
Planning for Legacy and Impact
Diggins’ career has been about more than personal achievement—she’s opened doors for future American cross-country skiers and changed perceptions about what’s possible in her sport. Similarly, thoughtful retirement planning often includes consideration of the legacy you want to leave and the impact you want to continue having.
This might involve estate planning to ensure your assets transfer efficiently to heirs or charity. It could mean establishing educational funds for grandchildren or supporting causes that matter to you. Many retirees find that having a sense of legacy and ongoing impact makes retirement more meaningful.
Consider how your professional expertise might continue benefiting others after retirement. Like Diggins moving into coaching, you might mentor younger professionals, serve on nonprofit boards, or teach courses in your area of expertise. These activities can provide both purpose and supplemental income during retirement.
Frequently Asked Questions
Where does Jessie Diggins live now?
Jessie Diggins currently resides in Minnesota, where she continues to train and prepare for her final competitive season. She has maintained strong ties to her home state throughout her career and has indicated she plans to remain in the Midwest for her coaching transition.
How many gold medals does Jessie Diggins have?
Jessie Diggins has won one Olympic gold medal, which she earned in the team sprint at the 2018 PyeongChang Olympics alongside Kikkan Randall. This historic victory marked the first-ever Olympic gold medal for the United States in cross-country skiing. She also has multiple World Championship medals and numerous World Cup victories throughout her career.
Who is Jessie Diggins’ partner?
Jessie Diggins is in a relationship with Wade Poplawski, who has been supportive of her athletic career. The couple has been together for several years, and Poplawski has often been seen supporting Diggins at competitions and events throughout her skiing career.
Is Skylar Diggins still married to her husband?
This question appears to confuse Jessie Diggins with Skylar Diggins-Smith, the WNBA player. These are two different athletes in completely different sports. Skylar Diggins-Smith is married to Daniel Smith, while Jessie Diggins, the cross-country skier, is with Wade Poplawski.
Who is the best female cross country skier of all time?
While opinions vary, many consider Norwegian skier Marit Bjørgen to be the greatest female cross-country skier of all time, with 15 Olympic medals and 18 World Championship titles. However, Jessie Diggins has certainly established herself as the most successful American cross-country skier in history and one of the sport’s elite performers globally.
Who is Jessie Diggins’s husband Wade?
Wade Poplawski is Jessie Diggins’ long-term partner (they are not married). He has been a consistent presence throughout her career, supporting her training and competition schedule. Poplawski has largely stayed out of the public spotlight, preferring to support Diggins’ career from behind the scenes.
Who is Thomas Vonn married to?
This question appears to be unrelated to Jessie Diggins and her retirement announcement. Thomas Vonn was formerly married to alpine skier Lindsey Vonn, but they divorced in 2013. This has no connection to Jessie Diggins or her retirement plans.
What is Wade Poplawski’s background?
Wade Poplawski has maintained a relatively private profile despite his relationship with Jessie Diggins. He has been supportive of her skiing career and often travels to competitions, but specific details about his professional background are not widely publicized as he prefers to keep his personal life private.
Who is Skylar Smith married to?
This appears to be another case of confusion with WNBA player Skylar Diggins-Smith, whose husband is Daniel Smith. This question is not related to cross-country skier Jessie Diggins and her retirement announcement. Skylar Diggins-Smith and Jessie Diggins are completely different athletes in different sports.
Moving Forward with Your Own Retirement Planning
As Jessie Diggins announces retirement with thoughtful planning and clear next steps, she provides a masterclass in how to approach any major life transition. Whether you’re planning to retire from a 30-year corporate career or transitioning from any demanding profession, the principles remain the same: plan ahead, diversify your options, prepare mentally and emotionally, and ensure financial stability.
The key takeaway from Diggins’ approach is that retirement isn’t an ending—it’s a transition to a new chapter. By planning thoughtfully, maintaining your health, building diverse income streams, and staying connected to your sense of purpose, you can create a retirement that’s as fulfilling as your working years.
Start your retirement planning conversation today, even if retirement feels far away. Like training for Olympic competition, retirement preparation is most successful when it’s a gradual, consistent process rather than a last-minute sprint. Your future self will thank you for the time and attention you invest in planning now.
Disclaimer: This article provides educational information about retirement planning strategies and draws insights from public career transitions. It is not personalized financial, legal, or tax advice. Your retirement situation is unique—please consult with qualified financial and tax professionals before making significant retirement planning decisions.
