25 Things I Don't Want to Regret Once I Retire: Take Two

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Since posting the first part of my list of 25 ideas and goals that I want to live by and be able to look back on with pride when it comes time for me to "hang it up". I've reformed the list in the past couple days, especially after reading all of your great comments. Without further ado, the exciting conclusion of "25 Things I Don't Want to Regret Once I Retire": 

13. Charity: Not Just For Suckers

I have many clients with some serious charitable inclinations, we're talking people who give away their entire fortune to charitable causes. Now, I have no problem throwing $20 in the basket at church on Sunday, but I've always been speculative about giving away all of my wealth. The reality is, I don't think giving to charity has to be so extreme (although it does seem very nice) and the giving does not have to be cash-focused. Giving away used household items, cell phones, books and electronics not only will satisfy my thirst for social justice, but will also provide me with a nice charitable deduction (assuming I follow the rigid IRS guidelines).

14. Invest 

This is open-ended on purpose. My definition of investing wisely probably differs greatly from other people's definitions. I think good investing involves a blend of traditional investing techniques, including stocks, mutual funds, etc. But I firmly intend to dedicate the bulk of my investing in non-traditional areas, including peer-to-peer lending (Kiva and Prosper are great starting points) and community investing. What I mean by community investing is that I intend to pour money into my local community and hope that the investment serves to purposes: urban gentrification and putting a healthy chunk of change in my pocket.

At my church I'm currently spearheading a project where we have arranged to purchase a home in tax foreclosure from the City for $1, and in exchange, we will rehabilitate the house and "flip" it, the only catch is that any prospective buyer must agree to owner-occupy the house. All told we will be doing a great community service by cleaning up a drab property, put money in the church's bank account and provide a fresh tax-base for the city (don't worry the house is vacant, we wouldn't be kicking someone out of their home).

15. Trim Expenses At Every Opportunity 

Once I "saw the light" and began creating and living by a monthly budget, one of my greatest joys was to pour-over the budget and look for places where we could cut back. This got to the point where it became thrilling for me to call my cell phone or cable company and haggle with them so we could save $20 a month. I'm not saying that I want to be cheap, because my spending habits clearly indicate that I am not, but I enjoy paying no more for basic services then is absolutely necessary. This is a lesson most millionaires understand, but most of the rest of us fail to grasp.

16. Use Credit Cards Wisely

I can't do credit card arbitrage like My Dollar Plan, but I am making a concerted effort to get the most from the credit cards we do use. Currently the Amex Blue card is "jamming me up" because the balance is rather high and the 0% APR is long gone, so we're struggling to put together either a couple of cards with smaller limits to port the balance over to, or possibly open up a credit card with a new credit union account and convince them to give us a huge spending limit on the basis that we will bring them a ton of business (cross your fingers). Either way, I don't trust credit card companies, and no longer like to pay for things with money I don't have, so not using them makes my life simple. 

17. Less Is More

Before I discovered the wide world of personal finance, which was expanded thanks to this post from Clever Dude, I would try to impress people I knew by buying them expensive gifts, or wearing expensive clothes. I rationalized all this with the "it's okay I'm going to be a lawyer" mentality. My revised approach is that I can still dress well and provide for those in my life, but in a frugal manner, which actually makes shopping, spending and saving a lot more fun.

18. Trust Your Lawyer, CPA, Financial Advisor (No This Is Not a Joke)

Sure maybe I have a vested interest in telling people to rely on professionals like attorneys, but the reality is that in most instances you will save time, money and heartbreak in the end if you choose to follow the advice of competent professionals. You've probably seen my post on estate planning, but this advice really extends into all realms. I know we are all personal experts on our finances, but it is no lie that a CPA can find more deductions for you than Turbo Tax. It's great to be able to self-manage your investment portfolio, but in the long run you'll probably experience better ROI if you rely on a broker/financial advisor. 

19. Insure Your Future

My next major purchase is a matter of life and death, literally. Within the not-so-distant future I plan on buying a fairly substantial life insurance policy on myself. No, it's not because the fiancee wants to trade me in for a new model (that's not a bad plan though) but I just want to make sure that my family is provided for in the absence of my premature demise. Although I am generally cautious of insurance companies, I feel equipped with the knowledge of what type of plan I am looking for, and am confident this is a wise purchase.

20. Family Matters

As much as I gripe about family problems, I do enjoy their company (most of the time) and look forward to being able to spend more time with them when I am finished with school. At the end of the day there is nothing more enjoyable then being with those you love and those are the memories I feel I will truly look back on and cherish.

21. Clip Coupons (Or At Least Recycle Them)

I used to just throw the coupon section into the recycling bin on Sunday morning. While that is still not an awful plan, I've started following the advice of several sites (including The Grocery Game) by stock-piling coupons for at least four weeks in order maximize my savings once items go on sale. I'm not as committed as some savvy CVS shoppers (you know who you are) but I like the idea of using little pieces of paper to save big pieces of green. 

22. Set Goals You Can Live By

This is a big deal, especially for those of us who follow GTD (Getting Things Done). I generally tend to survive to-do list by to-do list, so getting my tasks, goals, dreams organized and on paper is important to me. I'm not suggesting or thinking about making a grand production of my goals, I just like to know what my actual goals are, so I have something tangible to work towards.

23. All This Can Be Yours

Someday it would be nice to have children. At that point, it would be nice to pass along a lifetime of personal finance knowledge (including what mistakes not to make) to my children, I'm thinking something in the context of The Frugal Dad. I think that one of the most under-discussed issues in America right now is individual personal financial decisions. Although we discuss them often in PF blogland, these issues are rarely seriously addressed and confronted in Mainstream USA (unless your name is Suze Orman). I'd like to be open and honest with my children about finances, and how they can get into, but hopefully avoid trouble. 

24. Tomorrow Is Today

Putting things off until tomorrow is one of the worst decisions you can make in planning your financial future. When I receive the bills in the mail, I try to pay them the same day, when someone sends me an e-mail or calls me (except my friends who I am notoriously tardy in responding to) I try to return the e-mail or call by the close of business. I believe that these lessons should always carry over to my financial life, to the extent possible.

25. This Is Fun, Isn't It?

I always try to keep my sense of humor near the surface of finance issues, because like many other things, these topics are a lot easier to deal with when everything is kept in its proper context. I find it important to be serious about my money, but serious enough to know when to laugh, joke and let some things go (being transferred 25 times when I'm on the phone with Bank of America is a major pet peeve). All in all, it seems a lot healthier to laugh then it does to cry.

That's my list, I hope you enjoyed it and I really continue to look forward to seeing your reactions in the comments...