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Naked With Cash is the year-long series on Consumerism Commentary where seven readers’ households share their financial progress on a monthly basis. I’ve partnered with financial planners who will offer some guidance along the way. Read this introduction to learn more about the series.

Kathleen is thirty-one years old, single, and living in Portland, Oregon. She loves her job, even if it isn’t very lucrative. With her $33,000 income last year, she’s looking to make more money from “side hustles” this year, such as her blog, Frugal Portland. To learn more about Kathleen, read her bio here. Kathleen is on Team Sara, with Certified Financial Planner Sara Stanich.

Kathleen’s report this month, below, includes Kathleen’s progress over the three months leading up to the end of April 2013. Following Kathleen’s own self-analysis, Sara Stanich will offer thoughts from her perspective. Sara’s comments are followed by feedback from budgeting expert Jacob Wade from iHeartBudgets.

Sara Stanich, CFP appears courtesy of Stanich Group and Cultivating Wealth.

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In January, Consumerism Commentary will begin the Naked With Cash event and series. Several Consumerism Commentary readers will share their financial reports and analyses at the beginning of each month, with insight from financial planners and other experts. To introduce each of the participants to readers, I asked them to share where they’ve been, where they are, and where they’re going, and to describe their strengths, weaknesses, opportunities and threats.

Meet Naked With Cash participant SteveDH, the only participant in retirement. Here is his introduction.

I entered the Air Force at 18 after high school in North Miami with $25 in my pocket and $1,934 in the bank. During the 20 years I served in the military I got married, begot (neat word) two kids, completed a Bachelor of Arts degree in Business from Park University, and lived in Mississippi, Thailand, Nevada, Germany, New Mexico, Florida, Korea, Idaho, and Virginia, finally settling in Missouri.

The settling in Missouri was in 1985 when I retired from the Air Force and went to work for a well-established company. I worked another 22 years and retired at the end of 2007 at 60 years old. My retirement asset target was $500,000 and I achieved that by the time I retired, but the strength of my retirement finances lie in pension income rather than asset consumption.

Presently retired, my wife and I enjoy traveling in the form of road trips and cruises. Our kids are grown, have their own homes and have become quite successful. From a financial standpoint I’ve tried very hard to simplify both the recording and reporting aspects of our finances. I use Quicken and Excel but I still budget and focus on cash flow. In the short-term future my wife and I want to continue our travels, volunteer when we can lend a hand, and stay close to all of our family. Long-term we will attempt to maintain our health, accomplish whatever our tired old bodies will allow and try to ensure our resources will last as long as we do.

My investment strategy as discussed between me and my CFP is “conservative income.” When we get cranked up it’s preserve assets, reduce risk exposure, preserve assets, don’t blow it, preserve
assets, hang-in there and preserve assets! My first year of retirement was 2008 -– think about that!

My Investment allocation target is 50% bonds, 30% cash and 20% equities, and that’s what we maintain. For the last three years I’ve been converting traditional IRA assets to Woth IRA assets in order to avoid increased taxes when I have to take distributions. It’s the old “Pay me now or pay me more later” Fram commercials applied to tax brackets and RMD.

In the first five years of retirement the only dollars that exited our retirement accounts went to Obama in order to pay the taxes on the dollars we converted from my traditional to my Roth IRA.

All credit cards bills are paid in full monthly and we have no debt.

These are my major financial rules:

  • Live below your means.
  • Manage your big S. (Be careful how you say that. The S is Spending.)
  • Simplify your life and your finances. Keep it simple, senior!
  • The income statement rules!

Thanks for your continued reading, SteveDH! I look forward to seeing you participate in Naked With Cash.

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This is a guest article by Sam, the author of the blog Financial Samurai and the founder of the Yakezie Challenge and Network. He writes a column for Consumerism Commentary every other Tuesday.

There are 14 income selections one must choose on a particular online dating site my friend Craig recently joined. Take a look at these choices: Under $20,000, $20,000-$30,000, $30,000-$40,000, $40,000-$50,000, more $10,000 increments up to $100,000, $100,000-$150,000, $150,000-$250,000, $250,000-$500,000, $500,000-$1,000,000, and finally $1,000,000+. Wow. Talk about getting granular! Do people really need to know within the $10,000 or $50,000 range of how much one makes? Guess so, otherwise there wouldn’t be so many choices!

Craig is 32 years old, six feet tall and works as a project manager in construction. He doesn’t make a lot of money, with a salary averaging about $55,000 a year. That said, with dark brown hair, a nice smile, four-pack abs and a cheerful persona, he should be considered a catch by many women. Yet, Craig has an inferiority complex. $55,000 is only the fifth choice out of 14 from the income list! He often wonders to himself, How am I supposed to compete with the thousands of other single guys in San Francisco who undoubtedly make much more than me? Earning $55,000 in San Francisco is like earning only $25,000 in Houston.

Income infatuation is strong

Women love to say that it doesn’t matter what car a guy drives, how much he makes, or how much he’s worth. Instead, the gracious woman emphasizes personality, charisma, drive, and integrity! Yet, if this were really the case, why don’t surveys ask a guy to rate his charisma trait between 0 and 14 like they ask about income? Why isn’t there more emphasis on the various types of personalities and ambition levels instead of just one word, yes-or-no answers? The reason is women aren’t telling men the entire truth! High quality literature (like Cosmopolitan magazine) prove that there’s a lot more than meets the eye!

I believe everything is rational, and the 14 point income question is there because women demand it to be there, otherwise it wouldn’t be there! If enough ice cream shop customers demanded double fudge peanut butter cup ice cream with swirls of caramel, you can bet your bottom dollar that they’d find a way to get the flavor on the menu.

Don’t take it from a guy

It’s really easy to see things from a guy’s point of view. After all, I am a guy, so what am I supposed to do, pretend I’m a woman and psychoanalyze myself from a woman’s point of view? Maybe, but there is a better way. The better way is to simply ask women about this ridiculous 14 selection income field.

So I asked Jennifer, a professional woman with ten years’ experience in corporate America the following questions: Should Craig lie and say his income is $175,000 to make him seem more desirable? It’s not like his potential date can really verify how much he makes, especially if he takes her somewhere fancy. Or, should Craig be honest and go with the “love me for who I am” option? I expected Jennifer to choose the latter, and she did.

“Craig should be himself and disclose everything with honesty,” Jennifer says. “What happens if they get serious and she discovers he doesn’t make the $175,000, then what? She’ll start wondering what other lies Craig is telling.”

That’s all fine and dandy, but what does it matter if Craig can’t get a date in the first place since no woman wants to date a 32 year old man in San Francisco earning only $55,000 a year? Craig can’t even get in the door. Wouldn’t it be a better strategy to make him seem as desirable as possible, and allow him to bedazzle her with his charming personality and chivalry instead?

Jennifer smirked, and simply said, “Men.”

What’s a guy to do?

Craig has been on this dating website for over a month now but isn’t getting much luck. He gets several “winks” and messages, but he hasn’t been able to successfully get a woman to go on a date with him yet. He went with Jennifer’s advice and chose the $50,000-$60,000 level. Frankly, Craig is depressed by his bad luck and wants to just give up online dating together.

Every time Craig thinks about lying about his income, he hesitates because women continue to tell him they don’t care about income. Yet, online dating is so full of lies. The five-foot one-inch girl says she’s five-foot three. The slightly overweight guy takes a picture of himself in a black shirt in an upward looking photograph and chooses the “athletic” body type. The list of embellishments goes on and on; it’s as if one is disadvantaged if one doesn’t cheat a little.

Readers, what should Craig do? And consider the opposite situation: if Craig were to make millions each year, should he reveal the figure or pretend like he makes much less? I assure you that Craig is a good guy!

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