How to Take Advantage of Your ESPP (Employer Stock Purchase Plan)
In this issue:
- Latest in Retirement Savings & Personal Finance: Workplace Benefits like Flexible Spending & Telemedicine, AI Taking over Jobs?
- How to Take Advantage of Your ESPP (Employer Stock Purchase Plan)
- Tools & Tips: ESPP Tax and Cost Basis Calculator
- Market Overview
Latest in Retirement Savings & Personal Finance: Workplace Benefits like Flexible Spending & Telemedicine, AI Taking over Jobs?
Telemedicine and Virtual Care
Access to healthcare no longer has to mean taking a day off work or sitting in a waiting room for hours. With the rise of telemedicine and digital-first care models, employees across all age groups are now able to connect with doctors, therapists, and other healthcare providers from the comfort of home, or anywhere, really. This includes everything from routine check-ups and prescription refills to more specialized care like mental health support or chronic condition management.
What used to be a niche offering has now become a core part of many employer health plans. The convenience is obvious, but what’s equally important is the improved affordability. By reducing overhead costs and streamlining appointments, virtual care helps keep expenses lower both for employers and employees. And for younger workers who often prefer app-based or on-demand services, it aligns more naturally with how they already manage most of their daily lives.
So take advantage of this perk if your employer provides.
Wellness and Lifestyle Spending Accounts
More companies are starting to recognize that health isn’t just about doctor visits. It’s about how people feel and function day to day. Wellness and lifestyle spending accounts give employees a flexible way to invest in their own wellbeing, in ways that actually make sense for their lives. That could mean a gym membership, a meditation app, therapy sessions, meal planning services, or even ergonomic equipment for a home office.
The key is choice. Instead of one-size-fits-all wellness programs, these accounts let individuals decide what supports their mental and physical health best. For some, it’s running. For others, it’s yoga, nutrition coaching, or just time to decompress. It’s not just a perk. It’s a shift in how employers think about supporting the whole person, not just the worker.
Is AI Taking Over White Collar Jobs?
It’s no longer a sci-fi question. In the next five years, a growing number of white collar jobs may actually be transformed, or in some cases, replaced, by AI. And this isn’t just speculative talk. People at the center of the AI boom are saying it directly.
Sam Altman, CEO of OpenAI, has said large language models like GPT-4 (and the upcoming versions) are capable of handling tasks in customer service, paralegal work, and basic programming at a level comparable to, or sometimes better than, humans. He has openly stated that AI will likely automate large portions of knowledge work sooner than many had expected.
Bill Gates made a similar point, saying AI will be as significant as the PC or the internet. He highlighted jobs in legal writing, accounting, financial analysis, and education prep as likely targets for early disruption.
Anthropic, the company behind Claude, has been a bit more cautious in tone, but they also acknowledge that much of the routine “back office” work can be handled more efficiently by AI. This includes summarizing reports, handling internal research, and automating document-heavy tasks. Microsoft, which is integrating AI into Word, Excel, and Outlook, believes entire workflows can now be created and maintained by AI, with humans mostly reviewing and editing.
Here are some categories of jobs that could be affected in the near term:
- Customer support agents
- Legal assistants and paralegals
- Content writers and copy editors
- Junior marketing staff
- Research analysts
- Data entry clerks
- Financial modeling associates
- Entry-level software engineers
- Tutors or teaching assistants (especially in prep work or grading)
- Operations and administrative support roles
To be clear, not all of these roles will disappear. Many will evolve, and some may shift toward oversight, quality control, or more strategic decision-making. But the shift is real, and five years might not be a long runway in some industries.
The above jobs are most likely in danger within five years. Be prepared and if you can’t beat them, join them!
How to Take Advantage of Your ESPP (Employer Stock Purchase Plan)
Just like employer 401(k) contribution match, ESPP is a workplace benefit that you shouldn’t ignore. Below we summarize some key points on how to benefit from it:
1. ESPP basics are simple and valuable.
Your employer lets you buy company stock at a discount, often 15%, and sometimes with a “look-back” feature that makes the deal even better. Just by participating, you’re getting a built-in return. But whether to hold or sell depends on your financial situation and what you believe about the stock itself. The following picture depicts the key terminologies:
2. If you need the money soon, focus on tax and risk.
Selling right away may trigger higher taxes (ordinary income), but it lowers the chance of loss from stock movement. Holding longer may give you better tax treatment (long-term capital gains), but only makes sense if you’re comfortable with stock risk in the meantime.
3. If you’re considering it as a long-term investment, do your homework.
Just working at a company doesn’t mean it’s a good investment. Even the CEO and CFO can’t predict short-term performance. Focus instead on the industry—is it stable, high-margin, with pricing power and loyal customers? Then look at whether your company is a leader in that space. If the business is strong and the stock is fairly priced, the ESPP discount becomes a meaningful margin of safety.
4. Watch your concentration risk.
Even if you like the stock, be careful not to let too much of your net worth depend on your employer. Your salary, benefits, and job are already tied to the company. It’s fine to invest more if you have strong conviction, but for most people, it’s better to diversify. The ESPP can be a great tool, as long as you use it with clear purpose.
See ESPP Concepts & Tax Explained & How to Benefit from Your ESPP for more details.
Tools & Tips: ESPP Tax and Cost Basis Calculator
The ESPP Tax and Cost Basis Calculator helps employees participating in an Employee Stock Purchase Plan (ESPP) understand the tax implications of selling their shares. It determines whether a sale qualifies as a Qualified or Disqualified Disposition and calculates ordinary income, capital gains, and the applicable taxes based on user inputs. This tool is especially useful for tax planning and maximizing ESPP benefits.
You enter the above data and it will calculate and produce the following results:
Market Overview
US stocks experienced strong recovery in May: the S&P rose 6.2% & tech stock heavy Nasdaq Composite delivered 9.6%. This is likely to reflect investors’ belief that the current administration’s tariff policies won’t affect the economy much. Whether this is correct or not remains to be seen as some believe that the impact of the raised tariff rates will start to show up in the coming months.
The following table shows the major asset price returns and their trend scores, as of last Friday:
| Asset Class | 1 Weeks | 4 Weeks | 13 Weeks | 26 Weeks | 52 Weeks | Trend Score |
|---|---|---|---|---|---|---|
| US Stocks | 2.3% | 5.2% | 1.8% | -1.3% | 13.7% | 4.4% |
| Foreign Stocks | 1.3% | 4.1% | 9.2% | 11.5% | 13.3% | 7.9% |
| US REITs | 2.7% | -0.1% | -4.3% | -5.8% | 12.0% | 0.9% |
| Emerging Market Stocks | -0.9% | 2.1% | 6.9% | 5.6% | 11.5% | 5.0% |
| Bonds | 0.4% | -0.4% | -1.1% | 0.0% | 4.0% | 0.6% |
More detailed returns and trend scores can be found on MyPlanIQ.com Market Overview.
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