If you hit the rewind button and I had to start over, I'm not sure that I'd do things much differently. I'd still want to explore different methods, approach other concepts with a degree of "yeah but" skepticism, and feel obligated to make my own path. I still would've been too busy with career & family to spend as much time learning about investing as I have since ER. However some of today's tools have proven to be much more useful than others.
If you'd come to me in college and told me that in 30 years I'd be ER'd and living in Hawaii with two hot chicks, not only I but all my relatives & acquaintances would have laughed heartily and then ignored you.
Your Portfolio: Setting it up for ER (The type of securities and allocations)
Bernstein's "Four Pillars", FinancialEngines.com, and M*'s portfolio X-ray have really helped with asset allocation & diversification. These tools just didn't exist in the 1980s, and the existing calculators generally started at age 65. I remember deriving formulae from tables just to extrapolate them back to age 40.
Your Portfolio: Mutual funds slice/dice, all-in-one funds, individual securities.
I'd pick low expense ratios over just about every other feature of a fund. Back in the early 1980s there was quite a penalty for changing your strategy-- 2-3% fees, $75 commissions, and much higher taxes. Even Schwab's "discount" brokerage was still catching on, so picking stocks really forced a buy&hold commitment and encouraged DRIPs. Otherwise all three of the above choices meet the needs of investors' different temperaments & analytical interests.
Managing your income Stream (e.g., volatility, inflation, etc): Pensions, annuities, harvest funds, etc.
I didn't choose my career because of its pension. I wouldn't pay someone else to hand me my allowance, although annuities are useful in some niche situations. "New" ideas like harvest funds tend to be overoptimistic and subject to retrenchment, so I'd tend to avoid anything that hadn't been in practice for at least a decade.
If choices hadn't been dictated for me, I'd teach myself to manage a lump sum and probably live mainly off its dividends (with some principal consumption). No complaints with the current system, though.
Again not my choice. But I tend to favor incentives for healthier lifestyles, cheap preventive care, and perhaps a higher co-pay for excessive use of the system.
I think one reason that the automakers are in such dire fiscal straits today is the price they're paying for their failure to deal with union/retiree healthcare issues in the 1970s & 1980s. Now that state & municipal govts are required to assess those costs, as well as industry, I think everyone's realizing that it's better to shift the burden off the corporate books and onto some other entity. It'll be interesting to see how unions manage their own healthcare plans.
I'd be very skeptical of any company that said "Stick with us, kid, and we'll take care of your healthcare until Medicare!!"
Unexpected things that went wrong that made you adjust or impacted you (e.g., health problems, money short-fall, etc.)
There are two huge lifestyle issues that age/experience have given me a better perspective on:
1. Starting a family will realign your priorities and create a conflict with your career. Any boss who tells you otherwise has 24/7 live-in childcare, is childless, is divorced without custody, or is delusional. Unless you plan to choose one of their options, you will probably need to choose a new career plan.
2. It's a mistake to stick with a sucky career for a great pension. Rationalize that choice as much as you want, as long as you realize that you're merely estimating the severity of the mistake. It's far better to seek a great career even if it has a sucky pension.
pre-FIRE - fix/replace the roof, redo the driveway, paint the house, repair or relace the furnace, water heater, refrig, stove, winter rat car while still w*rking.
Did you really juggle all those tasks while you were working? Or, like many of us, did you retire and take a deep breath before you started working on all the deferred maintenance?
Even today I have trouble finding contractors who will come out to the house, estimate the job, show up to do what they promised, and do it well. In many cases it's easier & cheaper to teach ourselves to DIY.