As many of you know, four years ago I lived in a studio apartment in Silicon Valley. In 2007 when I moved in rent was $905 a month, utilities included. The next year, a big, evil apartment management company bought my complex and raised my rent to $1100 a month. The following year, when they raised it again to $1295 per month for the large, but definitely not luxurious studio, I moved out and got myself roommates.

I’ve never done well with roommates — both because I’m not always the cleanest of people, and because I can’t stand other people’s noise when I’m in the mood for silence. But this time around things worked out. One of the girls I live with is more of the mother type, so as much as my occasional mess bothers her, she helps keep me on track, and I do my part to keep my mess enclosed in my room. We’ve had one roommate move out, due to her schooling taking her to another part of the state, and my consistent roommate’s girlfriend moved in. She’s never home (she works until 11pm at night) and is very quite. The  motherly type roommate can talk a lot, but generally is respectful if I go into my room and don’t want to have a conversation. All in all, the living situation works out.

My apartment is in a condo complex and is quite lovely for the area. We have a complex pool, we are right off the freeway, and in the beautiful hills of Silicon Valley. The 3br 2ba is about $2200 per month total, and since I have one of the smaller rooms I pay $645 a month in rent. Utilities split come to $70 max, even in the cold months. When I moved in I was paying $605 a month in rent, so in three years it has only gone up $40 a month in rent, which is really not bad at all. I shudder to think of how bad my financial state would have been should I have stayed in my studio apartment (which is now going for nearly $1600 per month to first-time renters!!!)

But as I get older, living with roommates feels a bit juvenile. Yes, I have my own small room which can fit a full-size bed and not much else, and a large shared living room which is decorated relatively nicely by my roommates (with my bookshelves and books being my only contribution to the space), but it just doesn’t feel like my home. I always feel like I’m living in their home. Which would be fine if I were single, but the fact of the matter is I spend a large number of nights each week at my boyfriend’s house. I feel comfortable with him, even in his free-standing wooden shed where he lives (it has internet and electricity but no plumbing or kitchen, you have to walk into his hoarder grandparent’s house for that.)

Now that he’s turned 30, he has perked up about the concept of moving in together. I’m ready for it too, but the finances don’t make a lot of sense. He made $25,000 in income last year (taxed at self-employment tax rates.) Living for “free” (he pays bills, for his car, and food, but not much else) he can live on $25k per year. Since he made so little, after taxes, he was able to take home $22k in 2011. He has $8k in an emergency savings account, and no other savings. No debt either, so he’s doing fine as long as he stays in his freemium model of living. As soon as we move in together, and as soon as we think about our future, this all changes.

I made about $100k last year, maybe $65k-$70k after taxes. Putting out incomes together, $90k after taxes should be enough to live together, even though I’d clearly have to pay more of the rent. A decent 1br in the area goes for $2000 / month, maybe $1800, but after utilities that would be $2000 at least. Even if he were to increase his income substantially and we could split this 50/50, that would be $1000 per month or about $350 more per month, $4200 a year that could be put into my investing accounts.

On the other hand, moving in together would likely force my bf to get a full time job with a reasonable salary, which, in the short term, would reduce our spending ability quite a bit, but in the long term may enable him to increase his own earnings. It’s difficult to go from $25k to a $70k salary, but if you take a full-time job at $50k and earn basic income raises, eventually you will get up to $70k per year. Ideally together we will bring in $200k pre-tax by the time we have our first child, which would let us live on $100k per year, and have $30k-$50k for savings. But that also would require that we both continue to work full-time with no time off for parenting other than the few weeks one gets in the US from your job.

Regardless of the future, I wonder what is best for now. It seems like I should stay in my current living situation as long as possible, saving as much as possible, till the time comes when we get married and it is more rational to move in together. But I’m also tired of living like a young adult with roommates when also having a very stable, long-term, committed relationship. And I’m even more tired of spending so many nights in my boyfriend’s shed, without plumbing, and having to wander through the woods in the middle of the night to get to the main house, where I trip over his grandparent’s mess, and eventually find the one bathroom in the house with no working sink.

That’s $83,022 left to save, or approximately $4.9k per month for the next 17 months. Since I only make about $5k after taxes, that, indeed, is an impossible feat. At best, with bonuses, I make $110k per year pre-tax, which comes out to an average of $6k per month. Still, spending just $1.1k a month for the next 17 months and obtaining all of my bonuses is unlikely, and yes, pretty impossible too.

My only hope is that my investments perform extremely well, and not extremely lousy ($163,747 of my total networth is currently in stock-heavy investment accounts.) I’m concerned my stocks will see losses instead of gains in the coming year, which will completely ruin my hope to be anywhere near $250k by November 2013.

5% interest, 18 months = $176,180
5% interest + $10k per year, 18 months = $192,125
5% interest + $20k per year, 18 months = $208,070
8% interest, 18 months = $183,784
8% interest + $10k per year, 18 months = $200,304
8% interest + $20k per year, 18 months = $216,824
10% interest, 18 months = $188,913
10% interest + $10k per year, 18 months = $205,819
10% interest + $20k per year, 18 months = $222,724

According to Personal Capital, my investments are currently 15% up in the last 6 months. That may not last. I’d like to see my account go up 30% this year, as then suddenly my dreams of $250k by 30 start looking a bit more possible. If they could make 30% for 1.5 years going forward, even without adding a cent, I’ll be at $242,710 by November 2013. With $10k per year of savings, that would bring me to $263.6k by 30, and would be a huge success.

I’ll be tracking my progress as always, to report on how close or far from the mark my investments are putting me.

Today, for the first time in 5 months, I drove to work. I could have gotten a restricted license 4 months ago, but I was afraid of driving again and waited until I felt I was ready. It also happened that today my company sponsored a drinking event after work. While I am not an alcoholic (according to my DUI class last night), I do find it difficult to refuse a drink when I am at a bar and the rest of my team is sharing a seemingly unlimited supply of wine.

I knew I had two options — either not drink, or have a drink and find another way home. Given I have not driven in 5 months, and how much I enjoy the freedom of driving, I found willpower to not drink. Yes, it was hard for me not to have any wine, when all of my co-workers (many of whom were going to drive home) were drinking multiple glasses, but I knew I had no other choice if I was going to drive. In addition to never wanting to drink anything and drive again, I have a 3 year probation with 0 tolerance, so I can’t even have a glass of wine and get behind the wheel. That’s for the better — it helps me focus on putting myself in social situations with lots of alcohol around and not drink, in case I ever need to drive home in the future after such a social event.

It is difficult — and frustrating — to be in a culture where it’s almost considered acceptable to drink and drive. Of course, no one thinks it’s acceptable to get shit-faced drunk and get behind the wheel, but I’m confident that many people have a couple of beers and think they’re “just tipsy” and fine to drive home, and they do. It’s frustrating because most of these people never get caught, not that I’d want them to suffer, but it’s also crazy how in my DUI class there are people who had .14% – .25% BACs and they are still upset they were in trouble.

The DUI class itself is fascinating. Yesterday was the last of my 10 “education” classes, which are now followed with 5 “process” classes. I have to pay about $650 for these classes. I’ve never spent a lot of time with people who drink a lot or party, but the class makeup is extremely mixed. You do have the people who clearly like to party and went out drinking the night away and woke up a hospital bed. But you have others who had a few drinks at the bar, thought they were ok to drive (or at least more ok than their friend who they went out with) and ended up being busted just over the legal limit because their light was out or for some other reason, unrelated to their driving.

Yesterday’s education class was a good one to end on, for this section of the program. The topic of the day was “addiction.” It was extremely sad to hear the stories of my fellow classmates, many of who had alcoholics for parents. One woman had a realization in the class that her husband was an alcoholic and she was gravely concerned that he was giving booze to her teenage kids who were drinking and driving, as she had given up drinking entirely since her arrest. Others are just angry they were caught and claim they felt fine while driving, even at .16% BAC and higher. It’s funny that I get angry at them, such as a guy who had a .23% and was driving with kids in his car at the time, and I want to shout “dude, you had three kids in your car and a .23% BAC, you have no right to be angry at the police.” I think we all judge each other, but in the end our punishments are the same, no matter if we were just over the legal limit or well over it, with or without kids in the car (well this guy’s lawyer was apparently really good.)

While I didn’t relate to being addicted to alcohol, persay, the topic of addiction really hit home for me because of my food addiction. Sometimes that does seep over to alcohol but for the most part I drink when I’m with people, and don’t hide my drinking. I do often hide my binge eating. And the addiction topic made me reflect on just how important it is to have willpower. So today, when I was at the bar, I forced myself not to have a drink. I knew I wouldn’t drive home if I had even a sip, but it wasn’t worth it. Just like junk food is evil and uncessary, so is alcohol. It’s a shame it’s so accepted as part of our social culture. I’d rather avoid it entirely. They don’t preach total abstience in class, but ultimately I don’t understand the point of drinking if it’s not to escape and have a good time, which often amounts to doing something embaressing or having a lapse of judgement. It’s very hard not drinking around other people who are drinking, and I hate seeming so stiff, but ultimately I think I need to quit drinking for good — along with junk food — and any other form of binging that I seem to have such a talent for. Only when I can learn how to avoid binging on anything bad for me will I be able to be a healthy person.

Yes, there are plenty of ways, such as adoption, to have children if you cannot reproduce because you’re too old or infertile, but a tiny, fast-growing part of me wants my own kids. I guess ultimately I feel like the purpose of life — if you choose to believe in a purpose — is to reproduce. Not everyone can do it and it’s not good for everyone to do it because of overcrowding. If I really wanted to not be selfish (unless you ask my mother) I’d avoid childbearing and help reduce the taxing on the environment of yet another human being.

Forgetting logic, though, I really do want to be a mother. Still, I’m terrified for so many reasons…

• Will I be a good mother?
• Am I just attracted to the idea of children because I feel like life has no purpose?
• Can someone like myself actually be a mom? I can barely mange myself!
• Will I regret having children because I’m terrible at commitments and this is something that clearly you can’t go back on…???
• What about money? How are you going to afford kids? Yes, you’ve managed to save up $180k in investments and savings, and have a stock package that has a small tiny chance of being worth enough to put you over the $1M networth mark by 40, but raising kids is extremely expensive, and with small houses costing $1.2M, can you really ever give your children the life you want to give them, instead of one that leads you to debt?
• Wouldn’t you just be better off continuing to work throughout your life and saving money?

Then, I remind myself that there are plenty of people who make much less than I do, and heck, are probably less responsible than I am, who have a child, or a few of them. That’s not to say they should or that gives me a right to go off and reproduce, but it gives me courage that I’m probably not going to be the worst mother on earth. I already know that I have so much love to give and have been waiting my own life to have someone or someones to give that love to.

I’ve been reading a lot of posts online about mothers who regret having children. Most complain about having no time in their lives to do the things they enjoyed — travel, go to galleries, hang out with friends, read a book — and it so happens I don’t have the time for that now with my work schedule, so I can’t imagine I’d miss too much. I’m sure it would be extremely hard for the first few years of having children and I can’t even begin to imagine what it would be like, but at the very least I feel pretty confident that I’m tired of freedom in my life and want something to life for.

It doesn’t help matters that so many of my friends are posting photos of their adorable first or second children — just born — with big eyes staring out at the world, so innocent and pure. I feel so confused looking at these images — part jealously, part awe, part horrified of what that means. Life is going by so quickly — I return home to my family a few times a year and each time I’m there everyone looks like they’ve aged another decade. My father is ill with termial cancer, my mother is neurotic as always yet turning into an old woman, her skin finally wrinkling as she approaches 60. My cousins and aunts and uncles aren’t who I remember them to be anymore. My family has grown up without me — which is my fault, having made the choice to move away — but I’m ready for a family to grow up with me.

My boyfriend certainly wants children. Half the time all we talk about is our future together with our kids. Other than his inability to obtain a full time job for the entirety of his 20s, he’ll be an absolutely wonderful father. I know that he’s the one — sure he’s not perfect, but he’s loving, smart, and wise, as well as more idealistic than I’ll ever be. I could (somewhat) easily find someone who has a more settled life, but ultimately I’d be too scared to live up to that person’s expectations of a wife. With my bf, I know he loves me for who I am, with all my many imperfections. And I love him in return, and despite being freaked out by the financial story of our relationship, I will always be with him.

It could be worse. He could be in debt, or have terrible credit. The good news is that he’s very smart with money, with the exception of making it. He lives in a free-standing structure behind his grandparents house and doesn’t have to pay rent, just basic electricity and internet. He’s received help for his car and covers gas and food with a part-time job, for which he gets paid to little for his role and experience. But he isn’t in debt. His parents aren’t wealthy, but they’re extremely frugal, and when the time comes both of us theoretically will have an inheritance of some sort from both sides. Today, he doesn’t have savings or a retirement account, which is concerning. Then again, deep down I feel like I’m the one who has to be the breadwinner and I’ve put all my chips on this startup where I was an early employee and – though odds are I won’t get rich from it — where I may just be able to eek out some life security without being a slave to work throughout my children’s lives.

The trouble is — what if that fantasy doesn’t work out? What is my stock ends up being worthless? Yes, I’m still being wise with my saving to some extent (I could be saving more, I bought myself a nice TV last month for $500 and managed to spend another $500 on Amazon odds and ends) but until I hit $1M in the bank excluding housing I won’t feel like I can have children. That cushion would not ensure that I can stop working, but it would make me confident that I could have the life I’ve dreamed of, and to somewhat — as a spoiled middle class person — expected. My bf doesn’t require any of the finer things in life, he’d be happy living in a tent somewhere, but I’d like an average upper middle class life for my family, and one where I don’t need to work 60 hours a week to obtain it.

But how long do I wait until I feel like this life is a real possibility before having kids? I know it is going to be extremely hard for me to have children no matter when I do it, and with 1.5 years left until 30, I’m panicing a bit. I don’t need to have children the day I turn 30, but I can easily see 30 turning into 32 turning into 40. I know I have about two years left until all of my stock is vested, so I’m commited to my current life for at least that long, assuming the company keeps doing well and I keep liking my job. After that — if all is going well — I’m sure I’ll have great professional options where my salary could increase, but I’ll be confronted with the dilemma of deciding on leaving the professional world to have a child or staying and putting off children for another few years, and likely never having them.

Ideal world, 2015 rolls around, I’ve just turned 31, I’ve been married for a year, and I am ready to take a break from the professional world to have children. And at this time, I’ve also at least saved $300k – $400k, which isn’t enough to put me at ease, but is enough where I could maybe have a child and not feel so scared about commiting myself and my family to a life of living paycheck to paycheck, or worse.

Where it hurts the most, though, is in my health. I’ve become so frugal that my brain tells me it makes more sense to put together a dinner of random snacks at the office versus coming home and cooking dinner (I’ll be too tired by the time I get home to do that anyway.) In one’s 20s, eating unhealthy and living unhealthy catches up to you. I’ve never been thin, but I definitely am noticing how as the years go on I put on weight much easier. Seeing the scale hit 180lbs was an eye opener. For years 155lbs was the number I’d hit if I were eating anything and not exercising. If i’m at 180 when I’m just 28, what will I be in my 30s?

Besides the number, the reality is that I’m already on my way to Type 2 Diabeties, I’m going to have tons of health problems later in life, I’m already so tired and lacking energy (I’ve been sleeping 9 hours per night and still feel exhausted each day), and what’s worse, it’s going to be incredibly difficult if not impossible to have children. There are so many reasons why getting healthy now is imperitive, yet each year goes by and I manage to come up with more excuses and find myself in a binge eating nightmare. It’s awful to admit, but I’m definitely a food and carb addict.

In 2 years or so, I’ll be getting married. There’s no ring on my finger yet, but we’ve already joked about the date, and we’ve been together six years(!) There’s a NY Times article about how brides will do anything to lose weight for their wedding day. I don’t want to lose weight just for my wedding day, but I do want to do it for my life. I’m even avoiding going home to see my family because I know they will make comments about how fat I am, one after another, with my dad, mom, grandparents, aunts and uncles all making some cruel comment about how I need to diet. Which is true. But nevertheless, it ruins an otherwise plesant conversation of how I’m doing well in my career and life otherwise (minus the depression and all that, but that’s easier to hide.) In the NY Times article, it calls out a bunch of popular fad diets that the brides were doing to lose weight. Most of them sounded absolutely ridiculous (a feeding tube through one’s noise and 800 calories per day? No thanks.) But one — the Dunkan Diet — sounded quite reasonable.

I’ve always been attracted to the idea of a low-carb diet because with PCOS and insulin resistance this actually is the healthy way for me to eat. My body is funny in that I don’t actually mensturate due to the PCOS, but the only times in life I’ve been able to actually have a natural period was by cutting out carbs and amping up on protein (mostly dairy.) I also briefly went gluten-free, which made my stomach flatten out quite a bit. I bet it had more to do with cutting out carbs versus the gluten, but it made a huge difference. So why is it so hard to just eat healthy and cut out carbs? It seems like if it’s clear this makes me feel better and healthier, I should just do it, right?

Part of it is the difficulties anyone has going on a diet. There’s fatty food EVERYWHERE. We have lunch at work and it always comes with a lot of high-carb sides. I tend to dislike the protein (how it’s cooked) and end up eating only bread, butter, and potatoes (plus junk food from our snack cabinet later in the day when I’m hungry again.) No wonder I’m fat.

Alcohol plays a huge role in my obesity. I don’t normally drink often, but lately my work culture is to go out to happy hour a few times per month, or to have beers at the office at the end of the day. While I can “not” drink (and I should not drink!) this is exceptionally difficult in my professional environment. For a few months after my DUI, I did stop drinking entirely, and it was awkward to order water when the team went out for beers. Yes, I could easily say I need to drive home, but so does everyone else and everyone else had at least one beer.

Finally, and this is a biggie, my lack of healthy eating goes back to not wanting to spend money. I’d love to have fresh produce and lean meats in my diet daily (especially fish!) but shopping for this brings my monthly grocery bill up by a few hundred dollars. I do end up spending a lot on dining out, but those costs are usually split between my boyfriend and myself. Worse, because we live separately, I often end up buying food and it going to waste because I’m always at his house and I’m never home. The worst is when you spend a lot on food and then it all spoils because you haven’t had time to eat it or prepare it.

Alright, enough with the excuses, right? I really want to commit to a diet for the next year and see how I can transform myself. I’d also like to start swimming in the mornings (there’s apparently a pool with practice in the ams before work near my office — it will be another relatively large monthly expense to join and hard to get myself there in the mornings for the workouts, but if I can do it than the cost will be worth it!).

I’m very interested in this Dunkan diet. It isn’t that new, but it’s gotten a lot of attention lately. It’s very similar to Atkins or South Beach, except it focuses on a healthier way of doing low carb (ie one cannot eat a lot of fat.) There are 100 foods that are allowed at all times and you can eat as much of them as needed until you’re full. Oat Bran is apparently an extremely important element of the diet as it fills you up. The diet starts with an “attack phase” where for 10? days all you eat is protein and oat bran. I’d be amazed at myself if I could get through that phase. It’s supposed to kick start your metabolism. Ultimately, though, what I like abut the diet is that it’s designed to set you up for a life of eating healthy and maintaining your ideal weight. They have a quiz on their site about what your ideal weight is, and although I’d really like to be 120lbs, my big-boned self will have to settle for 130lbs as a healthy person. Seriously, though, that’s 50lbs to lose and that’s still a lot. That said, if I were able to follow this diet and swim for an hour three days a week I know I’d be able to lose the weight. It WILL cost a lot, and I won’t be able to save as much, but ultimately who cares how much money you have if you’re a big, fat lethargic blob who is diabetic, depressed and cannot have children? I guess when I put it that way, it makes a lot of sense to invest in my health. If I don’t max out my 401k, the world isn’t going to end.

This is a question I ask myself day in and out, as I constantly corner myself in a rut I cannot get out of. It’s almost comical, on how I’m both incredibly successful and dinging myself left and right for each failure that I craft for myself. I’ve been through too many therapists to count, have outgrown adolescent angst, and still, here I am, so far ahead, so far behind, all at once.

Financially speaking, I am proud of myself, but feel I don’t deserve to be where I am, and feel deeply guilty for what I do have, yet also terrified of not having enough. My mental disorder(s) may be most easily defined as a cross between neurosis and narcissism, which is so deeply who I am due to my upbringing and fear of taking power over my own free will.

I sat in my bosses’ office the other day, with a goal to discuss my great progress and how I “deserve” a raise. Instead, I found myself being told that I’m viewed as a bit of a mess. People like me (which is progress from where I was as a kid), and people know I work hard (which I do), but ultimately I am unpolished. Instead of asking for a raise, I ended up holding back tears and having a good cry in a bathroom stall once I got through the very accurate and very painful critique.

The painful part comes from how this story has never changed, and it’s my fault. I spent my youth and adolescence assuming as some point I’d magically grow out of it. It’s possible I have a real chemical imbalance in my brain known as ADHD, or maybe it’s the depression, or some form of OCD, or maybe I just need to grow up. Ultimately, there are a few things that I know happen which prevent me from actually being able to win:

1. I feel stupid all the time. I work with a lot of really intelligent people, and I’ve always enjoyed being around intelligent people. I always feel like I need to “prove” my intellect, which never works, since I’m not smart. I feel there are two ways to success — either be really smart, or very talented at socializing.
2. Deep rooted need to “prove” to myself (and others) that I am, despite lacking elegance, able to be a hero and have an epic win. This probably comes from my parents being narcissists themselves, and bragging about my big wins. That’s probably pretty normal for parents, but it was more in how they did it. My victories always felt like nothing more than bragging rights for my parents, not about taking any pride in my ability to succeed.
3. Setting up scenarios where winning was extremely difficult and required a visible fight became an addiction. If something wasn’t hard, it wasn’t worth doing. But I wasn’t smart enough (or focused enough) to accomplish really hard tasks, so I started to make everything difficult. Cleaning my room, for instance — I’d avoid cleaning until everything had piled up and I’d have to spend hours going through piles until finally I might have a spotless room. Chances are, I’d never finish, but I wouldn’t feel bad because it was an impossible task. In the rare case I was able to finish, I’d get such a rush. It’s a true addiction, just like any other drug. Just putting things away on a daily basis, while much more practical, wouldn’t give me that rush. So I let things pile up. Today, I’ve had an epic cleaning day. I may even get through the pile. But then tomorrow, will I just be back to where I started, letting the mess pile up again? Probably. This is a problem. A huge problem.
4. I’m a perfectionist. Maybe even a little OCD. If almost everything is perfect but one thing is off, it drives me nuts. If everything is off, it’s almost calming. Again, like I don’t have any control over it, because it’s so bad, so I can just ignore it.
5. I’m an extrovert but I have no freaking clue how to talk to other people. I can be silly and make people laugh, sure, but, as I’ve written about before, I’m no good at small talk. I’m still much better than my boyfriend at being social, which is laughable, because I’m terrible. I’m bad at conversation. I like deep conversation about the meaning of life, and what makes people tick. Despite not wanting to be a gossip, I find myself only truly able to contribute to conversations when the topic is another person that is a mutual acquaintance. I am lucky that I have opportunities to socialize with my coworkers, who are funny, smart people, and who can talk to each other while I generally listen (or I drink — see my last post — and manage to communicate a bit.) Still, in the end, I feel sad because no matter how much money I have or how good my life is, I want to connect with other people, and it’s a daily struggle.
6. I don’t have any long-term goals that seem meaningful or achievable. When you’re young, life is broken up into years, and the years are long, and each year ahead is something to look forward to. You go to school and do your work so one day you can get into a good college and eventually have a great career and find a wonderful significant other, have two kids, and a house with a white picket fence, where you can have backyard barbecues and invite folks over for dinner. I really don’t know what I want anymore, and I don’t feel like I have a right to want anything. My financial journey is rooted in fear — fear of running out of money, fear of my mental health issues becoming so huge that one day I cannot work, and needing a lot in savings. At least this gets me to save money, and I’m proud I may be able to hit my goal of having $200k in various investments and savings by the time I turn 29 (on track to my major goal of $250k by 30), but this doesn’t make me happy. It helps me not be totally depressed, knowing I have cushion now, but I’m then looking at what happens if I get married and have children, and how I’ll need much more than $250k for cushion then. But, beyond money and savings, I’m not sure what I want. I guess I want a family, I guess I want to be a mother, I guess I want a house. But all the things I maybe want seem like things society tells me I should want, and perhaps things that biologically I crave, but will they really make me happy? I am well aware kids are not an expensive jacket you can return to the store. Do I have any right to bring another human being into this world? And shouldn’t I figure out a life purpose well before having children?
7. If I were to live a much simpler life where I didn’t set myself up for failure time and again, would I actually be happier? I am afraid I’d be bored. Or further depressed. Because the only real meaning I have in life right now is that addiction to making things difficult for myself and setting up situations where if I win it’s almost orgasmic and if I don’t then I can just accept it was impossible to begin with. That’s not a way to live life, however. And it’s certainly not a way to live life once you are in your 30s. It’s time to grow up, and maybe, somehow, just accept simplicity. It may very well be that is the meaning I’m looking for… being able to come home from work at a reasonable hour, and instead of turning on the TV and wasting away the evening watching bad reality shows, open up a book, go for a walk, draw something, do something meaningful with the little free time one has in adult life. Go for a walk in the middle of the day and actually see the sun. The epic meaning of life is in freedom, not being a slave to yourself or anyone else. Work should not be the meaning of life. It’s great if you love it, and it’s great if it provides your life some meaning, but ultimately, it’s a paycheck. Life is much, much more than that. I just want to learn how to live it.

It’s been six months since pleading “no contest” to my DUI arrest at .08% BAC, and 10 months since the actual evening of the arrest. I’ve gone through many phases after the arrest, including depression, shame, guilt, anger, and now, coping and trying to move on.

I’ve been without a car for months now — thought I’m eligible to register for a restricted license to get to work, I’ve been avoiding that and driving because I’m scared to let myself get near a car. On Monday, I’ve finally made myself a DMV appointment to purchase a restricted license. This summer, once my classes are over, I should be able to get a full license and attempt to bring my life back to normal, or better yet, move forward to a place I’ve never been — in control, and in charge of my own happiness.

In my DUI class the other day, we had to do an exercise called “the 12 hours before your DUI.” It had a series of multiple choice questions, that because with — “was it on a usual or unusual day?” For me, it was an unusual day. I was having a huge bought of anxiety and hadn’t moved from my bed for the entire day, not even to eat. I don’t even remember why I was so stressed, but I was having a bad enough panic attack that I requested to work from home that day. Then, around 5pm I decided it would be best to force myself to get out of the house and go to a meetup event, where I could try to be social and get myself some food. Unfortunately, instead of food, there was only wine and a lot more anxiety. So I had four or so glasses to drink on a very empty stomach.

The questionnaire went on to ask what time you started drinking, where you were, and what time you were arrested. I started at 7pm, finished at 9:30pm, and was arrested around 12:30pm. Why were you arrested? My option was “other.” Most people in the class had been pulled over for driving poorly. I have the lowest BAC in the class at .08%. Most people had .14% or higher, with a few .20% and higher. Some stories are so crazy (like the guy who got arrested with three kids in the back seat and a .24% and, because he had a good lawyer, got less of a punishment than I did with my .08% and no traffic violation) or the woman who was drinking all day and ended up driving with a .22% to help her friend out who forgot her seizure medication at a party. Most people were celebrating, a few had been drinking all night, went to sleep and woke up the next morning to drive, only to get a DUI because the alcohol hadn’t left their system.

At the end, the questionnaire asked four final questions:

1. Do you feel responsible for the events leading up to your DUI?
2. Do you think it was fair that you were arrested?
3. How likely are you to get a DUI again?
4. How hard will it be for you to get a second DUI?

We’re told that 40% of first DUI offenders will get a second DUI. That seems ridiculously high, but in forcing myself to answer these questions honestly, I understood why.

1. Do you feel responsible for the events leading up to your DUI? Yes, entirely.

2. Do you think it was fair that you were arrested? Somewhat. I think it was unfair I was arrested that night because someone called 911 on me walking to my car — not even because I was driving poorly — and all of the videos they force us to watch show accidents with people who had .15% or higher — but I also am glad they did because it was much better to learn this lesson on a night I was just barely over the legal limit, then another night when I might have been more depressed, more intoxicated, and hurt someone. I still think it is unfair how people who have clearly had a lot more to drink end up with the same punishment or even lesser punishment if they have good lawyers.

3. How likely are you to get a DUI again? Very unlikely. I wanted, so desperately, to put that it definitely wouldn’t happen, but then I wanted to be honest.

4. How hard will it be for you not to get a second DUI?  The only real way for me to guarantee that I will never get a DUI again is to stop drinking. Of course when I’m sober I can say I wouldn’t drive after I drink, but the problem is that when you drink you think irrationally. I’m a lightweight, and after even one drink my logic goes to shit. I am glad that this experience after the DUI is so frustrating — because it’s easier to “forget” paying $10k over the years, but it’s not easy to forget the night in jail, the five days of SWAP program where I was a part time convict and freedoms were taken away from me, and now, this year of my life which has been really difficult due to not having a car, putting a great deal of stress on not only my life, but also my boyfriend’s life, as he has so kindly helped drive me over the year. Somehow I’m managed to maintain my job this last year, but I’ve been severely depressed, and have gained more than 20 pounds, now at my largest weight ever. I feel so out of control, and so I just eat and eat. This is another reason I must get my life back in order.

Going to a CPA, I learned, isn’t a lot different from doing your own taxes online. I sat there with him for a full two hours reviewing my paperwork (which admittedly wasn’t as organized as it could have been) — but what took the most amount of time was him trying to understand my gains and loss statement for my Sharebuilder account, which — I thought for a CPA — should have been easy. He also was confused by my tiny Lending Club and Prosper interest, not knowing where to put it.

I expected to owe taxes this year, and really had no idea if it would be $3,000 or $10k, so I was prepared for the worst. In the end, the relatively good news is, I seem to only owe $3500 or so, plus the $500-$600 to the CPA. I can also sleep at night knowing a CPA filled out my tax forms versus my guessing on a few confusing parts of TurboTax. It’s a little bit of a bummer that I am paying $600 or so to file taxes, versus $100 online, but this also ensures my forms will be mailed in that have to be sent with a paper return.

This week, I also re-discovered the inefficiencies of the IRS and just how behind the times they are when it comes to technology. It’s amazing they let anyone e-file taxes to begin with.

In any case, I’m almost done with this filing. I need to figure out if a stock gain was recorded properly on my taxes last year, or if I need to count it in this year’s taxes. I’m on a life mission to get much more organized around taxes and everything else. It’s only going to get more complicated from hereon out.

This is something I think as a whole women are not good at, and when they are, they can come off as fake or backstabbers. Women who do really well in business are very attuned to how they present themselves, physically and verbally, at every instance. They know how to make allies in the right places. They still stand up for their own ideas and what they believe are the right decisions, but they are always one step ahead, carefully crafting their next move.

This is likely true of all business professionals, beyond those who are scientists and the like who are allowed to sit out the game in order to focus on generating innovation and new products. Even then, anyone who wants to manage that process needs to get into politics.

I wish they taught this in school. The biggest challenge is regaining your position and momentum once you’ve slipped. You have to view your entire professional career as a long, ongoing political campaign. You show what you can accomplish, who you can win over, what leadership power you have, even if you do not have direct reports. You must “make friends and influence people,” according to that popular book.

It’s the make friends part I’m personally terrible at. This is extremely challenging as it requires not only the ability to deliver collected, concise speech in the board room, it also requires just as much ability to talk over drinks about topics not related to work at all. This is difficult, especially as a woman, because more often than not you are not invited out to these events. You may be invited to larger — the whole team is going out for happy hour type events (usually I find I’m one of the few women who goes to these events) — but when it comes to the VP or CEO going out for a 1on1 dinner to celebrate success, chances are that’s happening between two men, not a man and a woman. There are exceptions to this, and I’m sure the women who get ahead know how to play their cards right. I imagine having children is actually a benefit here, as you can, on a non-professional level, discuss kids, parenting, and even have your kids hang out with the children of your colleagues while you spend time with the adults and watch a football game.

In any case, point is, if you really want to get ahead, you need to think like your own campaign advisor and plan every thing you say, wear, and do, in order to improve how your colleagues view you and admire you. Just like a presidential nominee would struggle from a failure in his race, so would any professional seeking to prove that one or two mistakes does not diminish their abilities to lead, gain collective trust, and make good things happen.

This year, however, I’ve decided last minute to have a CPA do my taxes. There are a few items I’m nervous about and want to make sure to get right. That said, I’m also extremely nervous about selecting a CPA — because they could easily be wrong too. Most CPAs that are good are booked solid until after the 15th right now, which leaves me a little concerned over the CPA I found that seemed to have a few (or maybe more) available appointments. However, in my neck of the woods where everyone is rich, I’ve found the minimums to do one’s taxes are $1500 or $850 (two real quotes I got), so the one person who quoted me $220 an hour with assistants costing $90 an hour, minimum 2 hours, seemed reasonable. Still a lot more expensive than TurboTax — which I’ll probably fill out anyway just to keep my records electronic (I wonder if I can save it without submitting) — and I doubt it will “save” me any money in the actual tax return, but at least I’ll feel like it’s done right.

I’m concerned about 5 particular items:

• 83b filing. You have to file that along with your taxes the year you make the election, and there’s no way on TurboTax to attach documents. I could fill out the paper form myself, but that would be putting a lot of confidence in my math abilities that i don’t have. I am also starting to be paranoid about the IRS never receiving my original “within 30 days” election (even though I sent it within 30 days) and want to make sure I get this right, just in case anything should happen later which would result in my being majorly screwed. I sent it certified mail with a return receipt but given I never mail anything anymore, I apparently did that incorrectly and never got the receipt, so I’m extremely concerned.
• Stock losses. I took a sizable amount of losses this year on a few big losses that were not going anywhere, so I could reinvest the funds left in them into more profitable companies such as Apple, as well as diversify internationally. I “lost” (not paper loss) more than $3000 this year (probably more like $6000), and I want to make sure this is filled out correctly and that any additional losses over the $3k are noted to be carried over to next year.
• IRA conversion. Last year I opened a traditional IRA with post-tax money because I thought I would end up making too much to qualify for a Roth IRA. I think that may be true. Regardless, if you make more than something like $6k you cannot use pre-tax money for an IRA. Which is stupid because if you don’t have a 401k then you have no way to set aside pre-tax money (unless you’re a real sole proprietor, in which case you can set up a solo 401k.) In any case, I want to make sure the IRS understands that this was post-tax money, so when I later do a Roth Conversion (ideally on a year I stay home to be a mother and have very low income taxes) I’ll be able to only pay tax on the interest on the account with a $5k basis.
• $20k of freelance income I forgot about — is there anything I can do to reduce the amount of taxes I have to pay on this? Probably not, but worth asking.
• General investment taxes — my taxable account dividends, P2P lending accounts, etc. It would just be nice to hear someone who does this for a living discuss if I’m doing anything wrong here.

Otherwise, my tax returns are simple enough to do via TurboTax. Other than the carried over stock losses, I assume next year they will be even more simple as I’m back in a full time job (hopefully for the remainder of this year) and not earning freelance income because I’m so busy with this FT job.

Have you ever used a CPA for your taxes? Do you feel it was worth it? How much did you end up paying?