It sucks.

When I was living in my office, I needed $1,000 a secure an apartment and actually have a place to live. I knew I was going to have that $1,000 in a few weeks, but didn’t at the moment. So, I borrowed from my older brother.

It turned out fine, in a few weeks I mailed him a check, and that was that. But still, I didn’t like it.

I’ve been pretty lucky that even though I owe still owe my mum a ton, she hasn’t freaked out too much. And that she hasn’t been charging me any interest, which is fantastic.

But even still, owing family money just blows. It can change the relationship in a negative way if you’re not careful.

As a rule, I would say never borrow from family or friends if you can avoid it.

Have you ever borrowed or lent to a family member or friend? How did it turn out?

The Main Issue: Expectations

The person I’ve been dating knows my entire story. She knows how much I owe, how I’m trying to pay it, and has seen me progress the last few years.

This has made our “date nights” incredibly easy. I have nothing to hide, and she doesn’t expect a fancy date.

It’s all about expectations. If you “date” like you’re not in debt…it’s going to get you into trouble. Either financially, or down the line in the relationship. One way or the other, it’s gonna get you in hot water.

Does this mean I’m an open book about my debt?

No, of course not.

Especially if you are meeting someone for the first time. Any sort of financial discussion is something you’d have further down the relationship line. Even my girlfriend who knows my whole situation doesn’t know exact income numbers (though she does know the debt numbers), that’s more appropriate for a marriage situation.

But are you taking your date to a $50/plate dinner for your first or second date? If you’re doing that and in some financial trouble…you are setting the expectations incorrectly.

And the reality is that if your date is “impressed” by fancy spending…is that what you really want? Especially when you can’t keep that up? That’s a recipe for disaster.

I’m in debt and want to date. Now what?

If you are in a manageable amount of debt, I don’t think you need to postpone a dating relationship.

What you do need to do is make sure you show your date that you are financially responsible. If you take her out and blow $200 on a first date, that’s going to look really bad when eventually you have to explain how much debt you are in.

However if you date within your budget, when it comes time to share more openly about your debt, you will look prudent and I’m sure your date will appreciate your foresight instead of trying to impress them with your play credit card money.

You don’t need a dime to have a great date

You don’t need to spend a dime to have a great date. Creativity and just being interested in your date is way sexier than a $100 dinner.

Here’s a list of 7 creative and cheap date ideas I wrote for Lending Club a while back.

Should you date when you’re in debt?

What do you think? Should you date when in debt? How do you handle dating when you’re in debt? Any great date ideas for someone in debt?

Coincidence?

Yes, and no.

I’ve definitely had more free time lately. Almost too much at times. Even though I always have work I could do, and as much as I enjoy my work, you just can’t possibly work 18 hours a day, 7 days a week. At a certain point, you just become incredibly unproductive.

But, I spent a number of friday and saturday nights working the past few months, and I can see direct results (in the bottom line) from those efforts.

However, even in a crazy situation such as mine, I need a social life.

Making Friends When You Are In Debt

I’ve slowly been developing a number of new friendships now that I rarely see my close friend anymore. It’s actually been pretty tough personally. My proactive approach seems to be working now. It’s taken a little bit of time, and it’s been stretching for me, but I’ve been invited to a number of social gatherings lately and even have been hosting a few of my own. Sweet.

It’s funny meeting new people and explaining to them how I work from home, and have been an entrepreneur for awhile now. Luckily my new group seems to like cheap entertainment! (that’s my kind of group!)

Will my debt issues come up?

Not likely. At least not in a bigger setting. In a smaller, perhaps 1:1 setting it might. If I was still living in my office, these new friendships would be nearly impossible to pull off without a larger explanation, so I’m feeling very blessed right now.

The Battle In Your Head

The biggest issue I think I’ve faced is really just in my own head. Being in so much debt really plays terrible tricks with your mind. No matter how many things are going well for you at the moment, it still hangs over your head. There is a constant battle to tell myself, “hey! You’re not a terrible person, people like hanging out with you!”

It’s really quite the mind battle.

Part of dealing with debt is also how easy it is to just hide away. When I’m feeling down, it’s very tempting to just hide away in my own little world, but that just makes things worse.

How Much To Share

As good as I was at covering up my trading addiction for years, face to face, I’m actually a pretty terrible liar. If someone were to ask me point blank about any debt issue, I would have trouble not sharing my situation.

Someday I hope to share more of my story publicly (besides my little blog here). I’m just not quite there yet. However in the next few months with a few of these newer relationships I see myself at least sharing part of what I deal with on a day to day basis. I can’t really develop deeper relationships if my friends don’t know what’s on my mind and troubling me. Good friends will pry, and eventually I’ll end up sharing more. And when that day comes, because of how hard I’ve been working, I think I’ll feel OK with myself and sharing a bit more of my story to people in “real life”.

While I’m happy for my friend, myself being a male, I’m seeing understandably alot less of her. More like once a week now vs. 3-4 times a week the past 12-18 months.

What has this meant for me and my whole mess? Well, mostly it’s meant more time to work on some side projects outside of “normal business hours”. In other words, prime time social time has turned into prime time work time.

I’ve made some other friends the last few months, and I feel like I “know” alot of people (names, basic facts, etc). But I don’t feel truly close to anyone here in Seattle besides my friend I mentioned above.

So, her getting a boyfriend has really opening up a whole lot of free time for me.

It’s both good and bad. It’s good that I’m getting lots done. It’s bad that I’m working on too many things at the moment (but time is allowing this for now). It’s good that I’m making money.

It’s bad (is it?) that I’m trying to make money on BOTH friday and saturday night this past week.

So far I’m up and down with the whole newfound freedom of time. At times, it’s very handy because I’m pretty motivated right now to work. But, like saturday morning….those big chunks of “free time” are actually a little scary.

Keeping myself motivated work-wise is priority number #1 right now. But in a close second is keeping myself motivated to take care of myself (keeping my apartment clean, doing laundry, running, hitting the weights). When I tend to slack on the second priority it really starts to affect my work motivation.

I guess it boils down to the fact that I work alot better when I feel better about myself.

So, does more time equal more money?

Right now, so far in my little experiment, it does. I’m not rushing to judgement just yet though. If this keeps up the next few months I’ll have a better idea of how this newfound extra time is affecting my bottom line both financially and emotionally.

“work is hard”, “my boss is mean”, “sally doesn’t like me”, “my boyfriend/girlfriend is being dumb”.

Really? Really? Are we going to make a big deal about this?

Perspective is something that especially in the past year I’ve always tried to keep. Perspective keeps my very real problems from overwhelming me.

The truth is that I am incredibly rich. I sleep in a bed (albeit a $30 too small craigslist one). I have food. I have family and friends.

I am rich.

I may owe 300K, and I am getting sued, but I’m still rich.

When 3 Billion people on the planet live on less than $2 a day….Yes, I am very wealthy indeed.

So some girl I think I’m perfect for barely knows I exist. At least I have a place to sleep tonite, a computer to write on, family and friends to love, and food to eat. What else do I need? (besides an extra 300K of course : )

In Arrested Development (one of the greatest shows ever!), the father of the Bluth family would use a one-armed man to teach his children valuable life lessons. Lessons about leaving a note, and not teaching lessons. Classic.

Growing up, my parents taught me all kinds of valuable lessons. Like, “don’t play with fire!” (I love the 4th of July), and “eat your vegetables”. Sadly, my parents never taught me about financial matters. It was a very taboo topic. Now after getting hundreds of thousands of dollars in loans, day-trading for 3 years, and almost losing everything (including my sanity), I’ve come up with 7 lessons I wish my parents had taught me before I went and screwed my finances up so badly.

7 Financial Lessons I Wish My Parents Had Taught Me Before College

Have you talked with your kids yet?

1. Know your FICO

Getting your free once a year credit report is great. But you really need to spend the extra cash and get your real FICO score. It doesn’t hurt your score to check it yourself. I’d recommend Myfico, you can get legit fico scores here from all three bureaus.

Your FICO score influences more than just rates on loans. It can influence your car insurance rates, even your ability to rent an apartment

2. It’s OK To Talk About It

In my family money was a taboo subject. As a result, I got my first credit card completely on my own. From there is was a sad spiral down the bad-credit chain. First one credit card, then 2, then 5.

My parents never talked about paying bills in front of me. They never talked about saving or investing. Money doesn’t have to be a taboo topic if you approach it correctly.

3. It’s OK to borrow

I remember when my parents refinanced our house. What they didn’t do is include me in the process. I was in Jr. High at the time and think of what a great lesson I would have learned if my parents had sat me down and explained the value of a 15-year fixed mortgage? Priceless.

It’s OK to borrow money when it makes financial sense. For example, lets say you have 10K in credit card debt at an average of 19% interest. You have a decent credit score….you should borrow to payoff that credit card debt. So long as you have the income to support it, you should refinance that debt at a lower rate (try a peer loan like from Lending Club). You’ll save in the long run, and you’ll be out of debt in no time.

4. It’s OK to lend

I wouldn’t recommend lending to family members, but a number of new web applications make it easy and even fulfilling to be a lender. Kiva allows you to lend money to microfinance projects in 3rd world countries. Lending Club allows you to lend to borrowers all over the US. It’s a win-win. You get higher returns, and the borrower get a lower rate because of the lack of a middle man.

5. It’s OK to take risks

It’s OK to take a certain level of risk with your investments. My problem is that I never learned how much risk was too much. I had no problem on forex investments that I could make 400% in a week on….that is a problem! Don’t go overboard with Risk, but look at your financial situation and your goals, and take risk appropriately. (learn how to trade forex here) If you’re 25 and all your investments are in a savings account, something is wrong.

6. Don’t Follow Stocks Day To Day

Following individual stocks that you’ve invested in is like watching a pot boil. You’ll go crazy and start thinking you can time the market.

My father worked at a company pre-IPO and so I was spoiled with my first real stock trade turning $100 into $2000 over a few years. Once the stock was public though, we would pretty much track it day to day. For a long term investment, you don’t need to know the daily closing price.

7. Ask for help if you need it!

Do you have trouble asking for help? When it comes to your finances, if you don’t know what you’re doing…you need some help. Talk to your close friends and see if you can get a referral for a financial adviser. If you’re totally clueless when it comes to investing, get some help! Just make sure to do your background research on hiring a financial adviser.

Had I known these 7 lessons I might have avoided some of the mistakes I made in my early 20’s. Don’t forget to subscribe! It makes me Happy : )

This week pretty much sucked.

Business wise, I got a few things done, but not much. I’m feeling anxious all the time now, and it just doesn’t make much sense. I’m in a much more stable point right now than say 6 months ago. Yet, I’m feeling more anxious than I have in years.

Doing the right things

I’m running, eating OK, sleeping enough (but not well lately, which is also new. It’s sometimes taking me an hour to get to sleep. Normal is about 15 minutes). I don’t have any girl issues at the moment. I did have a friend of a friend staying with me all week, I know that didn’t help, but I think it only aggravated the anxiety, not caused it.

My only thought is that it has to be business related. I’ve given myself 1 more year to finish out the business I started after college. I think it has the potential to get bought out, but that is still a long way off.

I took some Advil my friend gave me last night, and I slept like a rock from 1am-11:40am. But it still took me forever to get to sleep.

Where do I fit?

I feel like I don’t fit in anywhere. Maybe it’s because I don’t have a normal job like everyone else I know. I had a sort of coffee date with this girl recently, perfectly nice girl, and I totally had no clue what I was doing. I probably looked like I hadn’t been in public in months. I tried to just relax and be myself, but I was so nervous I’m sure she noticed. The thing with dating is that while I’m feeling anxious lately…I’m not depressed, in general I’m a very happy person, so…

I don’t know.

I have free time in the evenings, I’ve gotten better at doing things on my own and finding cheap non-work things to do. But I’m still looking for that intimacy relationally, you know? While my one friend is great, there is only so much I can share because we aren’t a couple and it just wouldn’t be appropriate.

Now I’m just rambling about women.

Looking at the title I put on this post I see dreams. I just had some crazy dreams involving paramedics and being in the army. It was weird but slightly exhilarating.

OK, I’m done. Go Seahawks.

If a girl were to read what I’ve written here…would they be repulsed? Impressed? Feel sorry for me? Think I was crazy?

What do you think? How much do I *share* about what is going on with me? I don’t want to just be like “blah!!!!” and spill my life story. But I also want to be genuine.

Grr….life man.

It ain’t always easy (especially with women involved! no offense meant…I’m just frustrated (mostly at myself of course…)

Even now, as I just got out of a spit bath shower using a pot of heated on the stove water, I feel so much better about myself. Not everything is hunky dory, no, not even close. But I am working. And I’m working hard. I’m not staying up til the wee dawn hours watching stupid charts bounce back and forth, praying they go the right direction.

Even as I’m contemplating filing a Chapter 13 bankruptcy I feel more like a normal person than I have in a very long time. Now, maybe that is strange, considering I have over 300K in debt. But at least I’m no longer adding to that debt!

Even if I file the 13 I will have an incredibly difficult road ahead. I will probably still be paying $1500 or so back to creditors. I will also have to live below my means so that I can send $400 to my mother each month. She would not even be considered in the bankruptcy, but I have to send her that money each month or she cannot survive.

Friendships 

In talking with my one close friend who knows about this, I asked if she would still be my friend (I wasn’t being too serious here, it was in a joking manner) if I declared bankruptcy, and was living in my office, and would have to check “ever declared bankruptcy” on those forms for jobs and the like. She replied,

“I’d still be your friend even if you had to check five boxes!”

Aww..I about cried.

(the other boxes are like “ever had a felony?” ect,)

Now that I’m not trading I don’t feel like I know some “secret” that no one else knows about. I can relate better with people, and I feel more like the person I was 4 years ago.

In the end, yes. But for a while I was like, “why am I doing yardwork in a home I am short-selling and that already has a good offer?” Plus, I spent $33 on bark, and flowers, and dirt. I was feeling really dumb. My bank account is overdrawn at the moment (I didn’t compute my business cashflow correctly and the last payroll run killed me). And $33 is not something I have to spare on a wasteful event! Let alone the time and energy to weed and clean and crap. Humph.

Then we actually started working. It was a beautiful day out, and spending time with my friends weeding was probably the most relaxing and fullfilling thing I’ve done in some time. I started off so bitter about my pride (why don’t I just tell my friends?), and ended up pretty OK with the situation. Yes, it was a “waste” of $33…but taking a little bit of good pride in my house made me feel not so crappy about this whole giant mess.

Still, keeping my whole debt fiasco under wraps is having more and more concequenses both emotionlly and financially:

• My friends eat out quite a bit (financial side)
• I’m having to lie about why I am selling my house (emotional side)

Responding To Some Comments

• I have not listened to Dave Ramsey’s show. But I have read alot on his site, and understand some of his principles. I know about the “debt snowball” method. I just don’t have ANY extra $ at the moment to pay off anything right now.
• The DMP rolled all the personal loans/credit cards that I had not negotiated to 0% or that were student loans. I kept a my old wellsfargo student card out of the program and another citcard one that I got for 0% for a year. I want to try and pay those off on my own
• I will be selling some of the bigger items around my house on craigslist in the next month. Thanks Charles for the tip about amazon for books.
• The new updated debt sheet does look ALOT better than the old $334,442 in debt one. BUT the only reason for that is the new one assumes I get my house sold. I may and likely will have tax liabilites from the short sale. I’ll update more when more happens
• Yes, I got 0% for 1 year on many of my credit cards. They only offer this after you haven’t paid them for many months. It’s not a fun route to go. When I went in for my last credit counseling apt they got a copy of my credit report. My score has gone from a 709 (when I bought my house) to now in the 400’s. Yikes.
• The 120K I owe my mother was not a loan. She put me in charge of investing her money, and I day traded it away. Of all my debts, this is obviously the hardest one on me. It has affected our relationship, but it has not destroyed it.
• I ran that tracert thing someone mentioned and the “casey” was from West Sacramento. So, there you go. Seems like it was really that guy.
• It seems some people like reading this blog. Thanks for the comments. I can’t post daily, maybe someday, but right now I have to focus on my business, and selling all my crap.