Imagine you go on a date with someone
They offer to pay for all your meals, coffees, etc.
But in return they say...
"If you break up with me any sooner than 3 years from now
I will ask you to pay me back for all that stuff"
Do you think you would be interested in that relationship?
Probably my favorite way to think about vesting when it comes to something like a work 401(k)
The FIRE movement has good and bad
Good → Financial independence
Bad → Retire early *if* you have nothing to retire to
Most people I work with enjoying retirement
Figured out what to retire *to*
Someone comes to me and finds out they have been laid off
We had been meeting quarterly year after year
So when they called and needed to me day of, we were ready
They said the meeting was invaluable because we:
- Already had all their info
- Could answer their questions in real time
- Adjusted their plan immediately for scenarios they had in mind
If this had been their first meeting in years, or a one-time engagement
This would have been chaos
It would have also required 10x the prep and 0% of the same clarity
There is nothing wrong with one-time or hourly plans
But when life changes fast
Ongoing planning turns these emergencies into actionable advice in the same week
Bonafide “financial emergencies” are rare
Failures to plan are common
But when true emergencies arise
You want someone on your side who already knows the ins and outs of your entire picture
“When should I take social security?”
Your benefit varies as you take anywhere between 62-70
If you take earlier than Full Retirement Age (FRA) → Reduced benefit
Delay past FRA → ~8% increase/year until age 70
Consider taking early if:
• Health concerns
• No other income sources
• Not working
• Financial needs
Consider delaying if:
• Expecting to live long
• Still working
• Have other income sources
What actually causes financial plans to fail?
Especially for W-2 earners?
After working with more than 200 households
These 7 breakdowns show up again and again:
7.) Not planning for “Financial Landmines”
Landmines are events that can blow up a plan overnight
-- Death or disability
-- Long term care needs
-- Lawsuits
-- Divorce
-- Major property loss
You can’t predict them
But you can protect against them
If you want to be work optional pre-65
Here is your checklist of items to get in place:
• Factor in inflation
• Plan for healthcare
• Stress test your plan
• Evaluate Roth Conversions
• Have something to "retire to"
• Save more into taxable accounts
• Understand early withdrawal rules
• Manage withdrawal rates carefully
Retiring with $10M or $500k
Higher net worth ≠ better retirement
It is less about how much you have
And more about what you plan to now fill your time with
Adequate Wealth + Purpose = Retirement & Life Well Lived
If you are planning to step away from work before your friends and peers
Pause and ask:
How will you spend your days?
It is easy to say:
“I will travel and see the world.”
But for most, that alone is not enough.
Think about it…
Even if you travel 4x per year, two weeks per trip, that is only 8 of 52 weeks.
Roughly 15% of your time.
What about the other 85%?
From experience, the happiest retirees all share one thing in common:
<< They find something to “retire to" >>
Ideas recently shared with me:
→ Golfing more often
→ Woodworking projects
→ Babysitting grandkids during the workweek
→ Part time consulting to keep the skills sharp
→ Working at a local coffee shop, because you love coffee
→ Volunteering 10 hours a week for a cause they are passionate about
Retirement is not just about stepping away from work.
It is about stepping into something meaningful that maybe isn’t vital to funding your plan.