Ready For Retirement

ames responds to a question from Chris regarding restricted stock units (RSUs) and how to avoid costly mistakes when managing them. He explores whether it’s wise to hold onto company stock or diversify for a safer financial future. He breaks down how RSUs work, from vesting schedules to the tax implications of receiving stock as part of your compensation package. He also explains the critical considerations you should make when deciding whether to hold or sell vested shares and how this decision fits into your broader investment strategy. Questions answered:Should I hold onto or sell my vested RSUs?What are the tax implications of RSUs, and how can I avoid mistakes?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - How RSUs work 4:24 - Like a cash bonus7:17 - Question your performance assumptions12:25 - How RSUs are taxed and paid15:14 - Default withholding rate and wash sale rulesCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Patrick and Mary will soon both be retired. They are curious about what their withdrawal strategy should be as they balance various retirement accounts, including a pension, IRAs, and a brokerage account. They've been using tax gain harvesting to minimize taxes and plan to eliminate gains by 2024. A key question is whether to withdraw from their IRAs or brokerage account first, considering their state’s tax exclusion. James explains that by managing withdrawals and Roth conversions strategically, some retirees can reduce tax liability, optimize income streams, and preserve the tax-free growth of Roth accounts during retirement.Questions answered:Should retirees withdraw from their taxable brokerage accounts or IRAs first to minimize taxes?How can Roth conversions and state tax exclusions be used to optimize income and lower taxes during retirement?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Patrick and Mary3:14 - Retirement taxes are different6:37 - Consider combined tax rates8:42 - Tax gain harvesting12:35 - Strategizing income in retirement16:48 - Realized gains20:12 - A twist on traditional thinking23:47 - The bottom lineCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Ben has been a saver his entire life, which helped position him for an early retirement at the age of 53. Yet, he faces a big challenge. Having maintained his modest lifestyle, Ben’s comfortable portfolio has continued to grow and has nearly doubled in value. James and Ben discuss the challenges of making mindset shifts and the proactive steps Ben has taken to encourage himself to spend more. Questions answered:How did Ben decide to retire when he was in his peak earning years?What are the steps Ben has taken to force himself to spend more?  Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Ben2:36 - A lifetime saver5:28 - Confidence to retire early6:41 - Retirement reality vs expectations9:12 - The appeal of retirement11:46 - The biggest challenge - spending14:13 - A growing portfolio17:33 - The lure of subsidiesCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Monique aspired to retire early, and while she had faithfully saved throughout her working years, she wasn’t sure if she had enough to retire. After getting assurance from professionals, she took the plunge and quit working. Monique and James talk about the first two years of her retirement – how she’s been able to focus on her health and pursue some hobbies she didn’t have time for previously. Monique also shares some surprising challenges related to spending, travel, and family dynamics. Questions answered:What can retirees who are natural savers (and have more than enough) do to loosen the purse strings and spend more?What does Monique wish she had done differently during her working years in preparation for retirement?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Monique3:58 - 5 years before retiring8:03 - Money impressions from childhood10:47 - Transition to retirement15:06 - Spending and travel challenges.20:50 - Family pressure and self-awareness25:51 - A spending exercise32:19 - Better physical and mental health35:53 - Persons and social changes39:01 - Advice for younger selfCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Elaine didn’t decide to retire at age 57, but changes in her company meant an early retirement for her. Being caught off guard, she didn’t feel emotionally prepared to make the shift, even though she knew that her family would be fine financially. One year into her retirement, she found her groove by focusing on her family, building new relationships, trying new things, and staying physically active. Today she says she’s never been happier. James and Elaine discuss how she found her footing in retirement, the advice she would give her younger self, and the plans she and her husband have for when they are both retired. Questions answered:How did Elaine find the activities and community she is now enjoying?What advice would Elaine give to others on the verge of retirement? Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Elaine 2:55 - The “decision” to retire4:44 - The loss of income6:05 - New social outlets and new routine8:15 - A year to make shifts11:19 - Advice for younger self13:58 - Search for activities; don’t say no16:21 - Challenges and advice18:37 - What’s next19:58 - Try new things; build relationshipsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

After his father lost healthcare coverage in retirement and had to pay for a major health event with savings, Derek was highly motivated to ensure sufficient coverage in retirement. He even considered leaving the job he loved for one with better healthcare and retirement benefits. Derek shares his retirement journey with James, including: ➡ Decisions he made pre-retirement➡ How he addressed healthcare concerns➡ How his perspective on life and giving back has shifted➡ How he and his wife prepared for the changes retirement would bring to their marriageQuestions answered:What are some questions my spouse and I could explore now in preparation for when we’re spending more time together in retirement?What is Derek’s advice for soon-to-be retirees?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Derek3:23 - Importance of healthcare6:48 - Health in retirement10:07 - A new perspective and purpose14:13 - Financial concerns and readiness16:29 - The biggest challenge19:30 - Adjustments in the marriage23:13 - Derek’s advice26:11 - Final thoughtsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Chris has been retired for a little over a year while his wife has continued to work. Now that Chris has “tried on” retirement and found the fit good, his wife will likely join him within the year. In his conversation with James, Chris, who could be described as goal-oriented and one who likes to be prepared, talks about the pros and cons of retirement. He’s found that by staying flexible, maintaining an adventuresome spirit, and focusing on giving back, retirement can be quite fulfilling. And he’s paved the way for his wife to retire with confidence.Questions answered:What sort of conversations could spouses be having before and during retirement about goals and expectations?How will relationships with colleagues shift and change in retirement?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Chris3:50 - Impressions regarding retirement6:17 - Preparatory conversations9:09 - Decompressing and adjusting12:24 - Purpose and mystery15:59 - Exploring and serving21:19 - Missing colleagues25:57 - One spouse retiring first29:41 - What’s next and final adviceCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Meet Joe Sullivan, who found the first few years of retirement very difficult. Community is important to Joe, but he wasn't getting sufficient, routine social interaction to make meaningful connections while living in rural Virginia. He found his groove once he moved to a retirement community in Florida.James and Joe discuss the phases of retirement and what those phases have looked like for Joe. Joe emphasizes the importance of remaining flexible and trying new things as retirees explore who they will be in retirement and what will bring them the most satisfaction and joy.Questions answered:How can I test the waters to see if a retirement community is a good fit for me?What is Joe's advice for new retirees?Submit your request to join James: On the Ready For Retirement podcast: Apply HereOn a Retirement Makeover episode: Apply Here Timestamps:0:00 - Meet Joe Sullivan3:07 - The decision to retire5:28 - Impressions vs real retirement9:11 - Needing something else10:39 - Retirement community decision12:05 - Before and after the move14:32 - Finding purpose17:16 - Phases of retirement20:08 - Joe’s advice22:05 - Emotional preparation24:32 - Next phase of Joe’s retirement26:07 - Final thoughtsCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Ready for Retirement is on a mission to be the most valuable source of retirement information in the world. In that light, we’re making some changes. The biggest change is that rather than James doing all the talking, he’s inviting people like you to be part of the show. Some of you have real-life retirement advice to share. Others of you have questions that James can address. Ready for Retirement is poised to be a place for both. Get all the details in today’s episode.Questions answered:How will the format of the Tuesday YouTube video and the Saturday podcast change?How can I participate? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps:0:00 - A new format1:41 - Upcoming podcast changes2:56 - Retirement makeovers on YouTube4:23 - How to participate6:39 - How to apply7:43 - Wrap-upCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!

Gary is a 73-year-old with $8 million in savings. Despite having substantial assets, he’s concerned about missed opportunities for Roth conversions as he faces significant required minimum distributions.James encourages Gary to reassess his investment strategy, particularly the bond funds in his Roth IRA, and align his tax planning with his broader financial goals. By doing this, Gary could make more informed decisions that support his retirement goals and charitable aspirations.Questions answered:How can I give money to friends and family without them incurring a huge tax bill?What advice do you have for someone who has more than enough but has a hard time switching from saving mode to spending mode? Timestamps:0:00 - Gary’s question2:04 - More wealth = less freedom?5:16 - The controlling factor7:22 - An exercise10:09 - Living life; investment allocation 12:49 - Giving considerations16:09 - Medical expenses considerations18:45 - Modeling 20:40 - SummaryCreate Your Custom Strategy ⬇️ Get Started Here.Join the new Root Collective HERE!