This week, I spent time with a good old friend who is now the mother of a one year old. Just a few years into the marriage, she says that if she could do it over again she’d get married for money. When you have a kid, she explained, they become your world, and all you care about is providing for them. Her husband apparently went to school for a certification and failed the exam, refusing to go back to take it again, and he’s stuck in his job making around $55k per year. Meanwhile, she makes a small salary as a hair dresser, and they both struggle to make ends meet. The pair bought a condo and, additionally, are paying off a car payment of $300+ per month. On the other end of the spectrum, sort of, I have another friend who is pregnant with her first child, and she’s married to an engineer for a major tech company, and even they are struggling with finances at the moment with a kid on the way and major house remodels. I kick myself when I share my concern about my boyfriend’s financial situation with her, as she’s struggling to pay off her debts as her husband pays for their expensive bay area starter home.

I’ve been scared to be with a man who has his life together. Because of my depression and other crazies, I just don’t trust myself to maintain a relationship with anyone who is focused on their career. I feel safe with my boyfriend, I know I’ll always be in charge of the finances, he’ll surely stay at home with the potential offspring, and maybe that’s fine. I just don’t know what I want. I can see myself going on like today if I don’t have kids, living with roommates, semi cheaply, splurging on dresses, shoes and makeup on occasion but overall keeping my living expenses low. Thinking about a life with kids changes the picture. And I worry one day I’ll be upset at myself for not seeking out a man who had his life together. Just enough to have a bit of retirement savings at 30.

It seems what destroys marriages is passive agressive bitterness about the things that one cannot change about their partner. They’re terrible with money. They aren’t sexually compatible. They don’t pick up the dishes. Suddenly there’s this grudge that makes two people who were once perfect for each other fall apart. And this may be a natural part of growing up, understanding yourself more and what you want. I just don’t want to get married without it being forever. And how can I commit myself to someone forever if I don’t feel like we’re on the same page financially. I want a reasonably nice house, which, in my area, will cost at least $1.5M. I want to take vacations around the world every couple of years with the family, once the future kids are old enough. I want to be with a person who inspires me to be my best all around. Someone who is contagiously, yet realistically enthusiastic for life… from road trips stopping at the motel 6 to catch some shut eye hitting the road again, to embracing the occasional luxuries and new adventures.

I don’t want to struggle with money at any point in my life. I’m still committed to having $500k in savings before I have children. It would be nice if my partner could contribute to this. I made a silly ultimatum the other day, to my bf, that before I say yes to a proposal he must have $100k in the bank. He has about $0 today. This means we won’t be getting engaged for a few more years, but I need him to prove to me he’s capable of achieving financial goals. $100k is a lot but not impossible. He lives at home, pays no rent, and if he had a job paying $60k per year, and let me pay for all our dates, he could save this much in three years. I’m willing to wait for that, because I know he loves me, but if he really loves me, in the way an adult loves another adult, he’d take on this challenge and strive to show me that he can provide some sort of stability in our lives.

And I feel like a TOTAL BITCH for requesting this. Who am I to want a husband who has saved money? Doesn’t that make me a gold digger? Well, maybe I am. Maybe I just want to be with a man who earns a six-figure salary, like I do, so we can have a comfortable life. It still won’t be easy in our neck of the woods, but my vision for my life will not be so far off the reality of it.

That said, what if he can’t save the money? Or doesn’t want to? Why not just get married now, have a family, and figure it out as we go like most people do?

Because I’d be bitter. I’d be bitter putting all of my savings to the life I want to have when he can contribute very little or nothing at all. That bitterness will destroy us. I need to be supportive now of his getting his life together. But I also am worried he will propose to me before he’s achieved this goal. Then what do I say? I told him not to buy me a ring. It is really just irresponsible to purchase an engagement ring when your salary is less than $15k from off and on freelance projects for the year. If he said to me, let’s go elope, let’s skip the rings, let’s save the money, and one day when I have a stable job and savings I’ll get you a ring, I’d probably say yes. Because that would show me he at least has achieved some level of financial maturity. But if he gets down on one knee with a ring that cost a few grand, I’ll be terrified, and won’t know what to say.

…so I just asked him to take the $5k he planned to spend on my engagement ring and to use it to start a Roth IRA. Propose to me by maxing out a Roth for just one year, to start his retirement savings before he turns 32. He doesn’t like it when I say things like this.

But stepping back further, I sometimes look at my life and what I really want out of it. My mother’s voice complaining that my father didn’t make a lot of money rings in my head. She wishes she married someone with more money, so her life would be easier. The truth is my father made quite a bit of money. Complaining about his obesity or his constant berating of her ego would be something sane to go on about. Instead, she would complain that we didn’t have enough money for all the things she wanted. But then I look at where I’m headed and think, oh my god, I’m about to embark on a life with a man who at 31 hasn’t held a full time job, has nothing in savings, and likely will not break a six figure salary until much later in his life, if ever. And I hate, hate, hate being a gold digger of any sort (or even a silver digger) as I don’t want money to factor into romance. I don’t want to be that type of women. But admittedly I’m unhappy about it. Does it matter that he has $0 in retirement savings and a good $5k left to his name that will be gone once he finds a job?

While I love him dearly, I’m attracted to men who are independent and at least a little driven. Not the ones who are so driven they forget that they have other commitments and a life outside of making money. But it’s hard being a professional woman surrounded by men who are, albeit imperfect in their own ways, at least able to maintain a real job. Now, my boyfriend has worked before, even at one point 30 or more hours per week, and he’s well regarded for his contributions. He just never took that and used it to move up in the world. His top-tier degree has gotten him nowhere without motivation. Meanwhile, a good friend of mine who spent much of his 20s in part-time positions on the road for a major alcohol label tour, who earned a degree from a basic online university, has gone on to work his way up, accidentally, to a vice president position at a major corporation. I don’t need my boyfriend to be a vice president but at this age (late 20s, early 30s) he’s just lost so much time in progress, and I worry that the rest of life will just be one big frustration like this.

The good news is if I want kids, he’ll stay home with the kids. I can work full time, have a job that takes me all over the world, and he’d happily be a full-time dad. He is not driven by anything but family. I guess that’s nice. I know if I were to leave this relationship and seek out another, it would be hard to find a man who is that dedicated to having a wonderful family. And those who are may not be interested in me for the long term. He loves me. He is the sweetest person and so often I feel I don’t deserve him. He is kind and generous. He’s done so much for me, from driving me to the airport when I need a ride to picking me up after I was unfortunately stuck in jail for the night after my terrible DUI experience. He is so giving to me yet he doesn’t have the ability to see all I really want is him to have a life of his own, passion for doing something that ideally produces a consistent income. He says he wants children but he has done nothing in the last seven years to prove that he is financially mature enough for this. He will say that people have children on all sorts of incomes, and that you don’t need a lot to have kids. Ok, you don’t need it, but I want to be able to have a comfortable life. Maybe take my kids on nice vacations every so often. Etc.

What drives me into further confusion is my own wealth story. On one hand, I’ve saved $225k at this point, give or take, and am on track to hit my $250k goal this year. I’m aiming for $500k by 35, and my first kid at 35. I also have a sizable amount of stock options which have the potential to bump me up a class or two, should luck shine on my company. One of my colleagues who I accidentally told about the number of options I have while I had one too many margaritas continues to joke to me that I’m a millionaire, which I continue to remind him is not true at all as valuation means nothing until a company is sold or goes public, not to mention taxes which cut down on any of this by quite a bit. I’ve been burned in the past on company stock options (being unable to transfer them to the new company stock because I was not an accredited investor, so ending up with $3/share vs $8+, at a time when I had very few options.) Still, my life story maybe changes with this, because if in a few years my company sells for something like $5 a share, I won’t be able to quit working forever (to live the lifestyle I dream of), but I’ll certainly have a lot more flexibility even if my man can’t get his professional life in order. And I know I’d rather be the one in the relationship with the money – above everything, it’s important for me to have the financial power or at least be a true equal to my partner here.

But – the stock option wealth is just a dream. It isn’t real. And the $1M minus taxes I’d have should we sell for $5 per share and I manage to fully vest isn’t going to happen. I mean, it could, but I don’t want to bet on it, I don’t want to get my hopes up and to watch that dream disappear. I need to be realistic. Practical. I need to prepare for those options to be worth nothing at all. And I’m doing that, mostly. If I thought I was an actual millionaire I would have bought a new car by now. Probably the Infiniti G37S because I’m turned on every time I walk by one, especially the newer models. I’d still buy it used, but probably a 2011 fully loaded model vs one from 2006. And I’d pay cash, because I could sell some stock and have the cash right now to do this. But instead I’m waiting until 2014 or at least fall to save up $15k to purchase a basic Toyota. And, alas, there are many millionaires who smartly don’t spend on fancy cars regardless (the personal finance community would taunt me for purchasing any car that costs more than $12k.) But if I were a millionaire, I might splurge on my housing – live in a 1 bedroom for $2k a month or buy a nice $800k condo versus sharing an apartment for $650 per month, and being sad about my roommates talking loudly at midnight when I’m having trouble falling asleep. Furthermore, I might spend more on life experiences, and pay for my boyfriend to come with me to exciting, exotic locations, since he cannot afford this himself. But I don’t know how much I’d really change. I’ve always felt that I wouldn’t consider myself rich until I have $5M in the bank, and that’s unlikely to happen ever in my life. Well, if my company sells for $25+ a share, in my wildest dreams, I could see something close to that in my bank account. Wouldn’t that just be absolutely crazy? Extremely unlikely. Lottery winning unlikely. I’ll be lucky if I get the cash back that I paid to exercise the shares early. At this moment, I look at my stock options as a loss, and pretend they don’t exist. But every so often I dream about what it would be like to be set for life by 35, knowing that it wasn’t via a trust fund or marrying into wealth, but due to my own negotiation skills and work abilities, and how it would effect my decisions overall. It’s not going to happen, so I don’t have to waste too much time fantasizing about it, but it’s fun to hold such a lottery ticket and hope.

Meanwhile, wouldn’t it be wonderful to meet a man who had that same goal, and then at 35 we together would have $1M in savings? Does this man exist and if he does, is he a terrible money-hungry asshole with no passion for love? I know many men around my age who are earning six figure salaries, but they are also spending a lot on expensive apartments in the city and lives that aren’t cheap. How much are they really saving? And when you go on a first date with someone, or even a second, third, and eighth, bringing up money is a big no no. Unless you’re meeting someone at a personal finance conference! Plenty of men are in debt as well. It could be worse. Then you also need to find someone who cares about having money as much as you do without them being too frugal or too wasteful. I felt miserable when dating a lawyer who would never pay for our meals. My current bf, unemployed as he is, still is always willing to take me out to a basic meal. Of course we’ve stopped going out to dinner because he doesn’t talk and it makes me depressed when I can’t converse over meals, so we’ve decided we won’t go to dinner together anymore. We go on other dates like to the movies and concerts, hikes and such, where talking is less important. And there’s nothing I love more than cuddling up in his arms. I’ve never felt so loved and safe. I can see growing old with him and always loving each other. In the long term money doesn’t matter. It’s in the short term that it does.

How long do I wait before he gets his act together? We had an agreed on ultimatum that by February he would have a job. Then his grandfather, who is 90+, fell down and hurt himself, having to move into a special home, and my bf was devastated. It took him a month to recover and be somewhat productive again. He’s such a sensitive person. I feel like such an evil bitch because I’ve learned how to stop feeling so deeply long ago. I had to in order to survive my life and to get where I am today. Still, there is such a softness to him that makes even the hardest parts of me start to bend. And we laugh together without a care in the world. In those moments where our cheekbones sprint towards the sky and we chuckle so loudly that anyone nearby thinks we might actually be psychiatric-hospital level crazy, I know what happiness is. And I’m not sure I should trade in happiness for any form of practicality. I just don’t know if I’d ever be able to find it again, especially in someone who cares about money more than they do about just existing and enjoying all of the priceless wonders of the world that are, in fact, available to experience free of charge.

I feel so awkward going into jewelry stores, or any fancy stores for that matter. We went to a couple this weekend. I felt absolutely in love with a sapphire ring with four side diamonds (it was “estate jewelry” ie pre-owned) and it happened to fit perfectly on my now 6.5 size finger. The same person who was, just hours before saying that she didn’t want a ring, was ready to bust out her credit card to spend $6k on this beauty. Still, I don’t want a multi-thousand dollar ring. I’d be perfectly happy with a basic white gold band with some meaningful inscription on the inside. Or, as I joke with my bf, ten thousand $1 plastic rings, so I’ll never have to worry about losing them and he can still spend $10k.

The whole wedding thing is bizarre to me. I’m still torn about the whole marriage concept to begin with. All of the fanfare is just symbolism that there is great meaningful to marriage that is bigger than what it really is — a business contract. I’m already theoretically committed, and have been for seven years. What’s the difference between now and after a ring goes on my finger or that we legally bind ourselves together? Well, the only difference I see is my life savings is no longer mine alone. I don’t know how I feel about that. And I think pre-nups taste dirty. I’d rather not get married, avoid the pre-nup, and just live out life with one person if that works out. If I end up having kids, then that’s the time to get married. Not now. There’s no point in signing such a contract before you’re pregnant. Romanticism be damned for a minute. It just doesn’t make sense.

He knows how I feel about marriage. To him, getting married is so important because his parents were never married and he had a very unstable childhood as a result of it. Meanwhile my parents were and they found every excuse to yell at each other, whether that be in discussing the “right” directions to the same location they had been to a million times or what they were having for dinner. I don’t recall one peaceful day in my household when both my parents were around. On the better days, there was just screaming. On the worse, there was my dad calling my mother an idiot and shoving her across the room, bruising her arm or breaking her glasses. My mom wasn’t strong enough to leave and my dad didn’t “believe in” divorce (because it’s “bad for the kids” – because calling your wife and idiot and beating her up in front of the kids is great for them to witness, but anyway, I digress…)

I understand why marriage is important to him and I want to respect that. I also am terrified of contractually signing my life away, even if it is to someone I love. I like my independence… even if it’s just used as a spare tire in times when life is getting flat. But I have to make up my mind soon. He’s not going to stick around with a woman who isn’t the marrying type. And I don’t want to be alone forever. He’ll be a great father. I love him to death. He puts up with my crazy. I love him for his, mostly. We’re kind of perfect together. So maybe I’ll end up with some gemstone on my finger in the near future. And, despite not believing in marriage, I’ll probably get married. And one day I’ll be a mom, which will be so strange. And then the years will disappear in recitals and practices and birthday parties. And I hope more than anything that somehow I can fight against the odds and manage to maintain a love so strong through all the years that I won’t miss the independence that I’ve grown to love. The freedom that poisons me with loneliness as it drugs me with desire for adventure and escape from the mundane.

Maybe a $5000 engagement ring on my finger would be the symbol of growing out of that phase of my life. It’s a symbol of commitment, love, honor, and, being owned by someone else. It’s willful slavery of the flesh in exchange for everlasting love. It’s stability, routine, and practicality. It’s being an adult. I probably do need a giant ass rock to remind me of that for the rest of my life, one that digs into my skin and leaves a bruise on my finger every day. Because love is brilliantly heavy. It breathes sweetness into my soul and washes away the athlete of seduction, the runner who trains for her next race, failing to fully realize that one day her legs will no longer work the same way, and she will be unable to run as far or as fast, and at that point, will she just be lying out in the field against sharp grass, crying out in despair over her solitude?

WAYBACK MACHINE: 1st HECC Post / May 27, 2007

This isn’t my first blog, nor will it be my last likely, but after randomly falling into the online investment blogging community, I decided it’s a good idea to start tracking my finances and the like via the Internet… anonymously, of course.

So here’s a little bit of info about me to get started: I’m a young professional in her early 20?s. I’ve been out of undergrad for two years now. My income is $35k a year, benefits included, except sans a 401k. Chance of raise/promotion within next year: 15%. Chance of company going out of business: 55%.

I’m fortunate in the sense that I have a decent amount of savings and no college loans. Savings from both my dad putting aside some funds for me for the awkward post-college year, and then extra cash from a lawsuit over a broken arm when I was little. My networth right now is around $27k. So I realize I’m better off than many other people my age, despite the fact that they might be making $50k a year and I’m only at $35k. Or at least our actual income after bills and other expenses is usually about the same.

Since this is an anonymous blog, I feel ok talking about the details of my finances. I haven’t talked about it much on my main blog since it feels weird letting people know about how much I’m worth, or not worth. But finances are one of the things that I really need to talk somewhat publicly about, since I’m unsure of how to handle my money, with the exception of spending it. I’m very good at spending it.

So I recently opened a few random mutual fund/IRA/CD accounts, as I’m attempting to “diversify” my portfolio. I know I’m supposed to be living under my means, but I often fail to do that and spend more per month than I take in. Obviously that’s a bad idea. But i’m hoping that at the least, putting some of my funds in high-interest accounts will balance out my poor spending habits.

Ok, so here’s the breakdown of my accounts right now… (I’m going to try to keep tabs of this, as well as my budget, on here)

$2,143.54 – Checking
$7,421.99 – CD – 3.1 % Interest, matures 8/28/08
$5,510.58 – Maximizer Checking
$1000.63 – Savings
$5,000 – 8-month 5.01% Interest CD
$3,000 – Vanguard Mid-Cap Growth Index Mutual Fund
$3,000 – Roth IRA, in 2050 Retirement Plan fund

Well, the last three of these items haven’t officially been started yet. I signed up for them yesterday. I’m waiting for all of the electronic transfers to go through. I realize investing in a Mid-Cap Growth Index Mutual Fund. Afterall, the smart thing to do is to invest in large caps, right? But I figure if I put $3000 into a mid cap fund, I can also invest in a large cap fund if/when I ever get a raise. I’m $1000 to maxing out my Roth IRA fund.

I don’t understand the Roth versus regular IRA option, being as I know the Roth is all after-tax income and the regular IRA is pre-tax income then invested. But what should I be investing in now? I’m only making $35k a year, so it seems like I’ll most likely be in a higher tax bracket when I want to retire. Afterall, I plan on making more than $35k per year when I’m 55 or 65 or whatever age it is I can retire.

And if I sign up for a Roth IRA now, can I move to a regular IRA at any time? Or am I stuck in the Roth?

Finally, how about my mutual funds – how much will it cost to change them from mid-cap to large-cap if suddenly I realize I ought to be a bit less risky in my investing? Gosh, I’m so confused.

$27,500 remaining to save (or $3437 per month.)

Looking ahead to what’s next, the big item up for auction is my devotion. That is, the next major choice in my life is marriage (well, unless I decide to buy a house first.) I’m extremely confused about marriage. While I’m glad we live in a day in age when women can be successful and independent, the options are almost too much. Do I even really need to get married? It seems marriage itself is good for two things — one, ensuring the woman is kept for if she is making less than the man in her life – and two, keeping families intact for children. Maybe there is some benefit to being with one person for the entirety of one’s life as you could say that there’s value in growing old with someone and not being alone, but who’s to say that one person will make it on earth as long as you do? In that sense, isn’t it better to have multiple close relationships so the odds of being alone later in life are less?

In any case, I’m looking at my seven year relationship and knowing that I’ll need to make this decision soon. Unfortunately it’s not the “get married or just stay with him and keep dating” choice. It’s either marriage or, I guess, we break up. And I don’t want to break up with him. He’s adorable, loving, committed, and would be a wonderful father. I also feel like I’ve made the mistake of not exploring enough relationships when I had the opportunity to in life… as an insecure serial monogamist, and maybe not the most attractive woman in the universe (I’d say I’m a 6/6.5 on a scale of 10), I’ve failed to date men I, well, look up to. I’ve also been scared of this coming from a family with an overly powerful father who was abusive and angry all the time. I wanted to have that control. And I didn’t think positively enough of myself to believe that I could be an equal with someone who had their shit together.

That said, I think I got really lucky with my current relationship. There are so many good things about what we have, it’s impossible to list them all. But of course it’s not perfect. And of course I wonder why lock myself into a marriage when I’m just now starting to feel like a person worthy of exploring my passions and people. I don’t really see myself doing that in my 30s… I think I want kids… and if I want kids then the reality would be rushing to find a partner in the next 3-5 years who I can marry and settle down with, and I  know full well that I’m going to end up regretting not sticking with my current SO if I do that. I’d be miserable. I’d miss him. I’d completely feel ill when hearing about him in another relationship. But then I think, god, isn’t that what most people go through over and over again in their lives — isn’t that what dating is supposed to be about? It’s not really something I’ve experienced. I don’t like heartbreak and I’ve never been strong enough to handle it. I’ve dated people before who I just wasn’t that into. It was easier to end things then. But now I’m 100% most certainly in love. And there has to be some value to being able to say that after being pretty much monogamous for over 5 years (we’ve dated seven, I had a little break in judgement on year two.) If we can make it seven years, than we can make it 100.

But going back to marriage, I worry, because whenever I think of marriage I think it’s a business agreement between two adult parties who contribute to a relationship and have their lives together. Although I still fear being with someone who has their life together, because then I feel less in control, it upsets me that he, after seven years of dating, has still not held one full time job. If he had gone to my high school and I would have never dated him. But I know he’s a smart guy, he went to a top-tier school and graduated with high honors, and I find that incredibly sexy, and I might be letting that cloud my judgement. He very well might get his act together soon — he’s applying to grad school, he’s considering a few different options, he knows he needs to make something happen. But that doesn’t change the fact that at 29 I’ve saved $250k and at 31 he’s now eating away at his remaining $10k in savings because he doesn’t have a job. I don’t need him to be wealthy, but yes, it kind of bugs me that after this many years, he has failed to showcase any ambition. I know he’s grown up in a very messed up family situation, he has no emotional support from his parents, but on paper I’m dating an unemployed 31 year old who lives at home. On paper, WTF.

Part of me wants to be the emotional support to help guide him to success. I know he needs that. It feels good to be useful, helpful. But I have my own life to worry about. I want to be with a man who inspires me to be my best person. Who shows me new things. Who wants to travel and try new things. Who pushes me out of my comfort zone as much as I love to stay in it. And that’s the itch. The itch I’m dying to scratch. I don’t know if it needs to be scratched in the context of a relationship or other people. Maybe I can just get a hobby. Maybe I can meditate like my therapist wants me to and find peace with myself. I can stop wanting. But I find myself so easily slipping down a destructive path. I want to be with someone who makes me feel inspired and alive and in the moment. But ultimately it’s the lack of motivation to find a job that hurts me. Because I feel like that- even though it’s about him – in a way it’s about how much he cares for me. Because he knows that, when I pull off all my romantic caps, I’m a realist, a realist with some expectations for my life. And I’m saving like crazy (almost) to try to achieve the life I think I might want. But he could have easily saved an equal amount by now, living at home, and moving up the career ladder. That makes me feel like, no matter how much he tells me he loves me, he really doesn’t. I often worry that I’m being a gold digger, but then, I don’t think it’s unreasonable to want to marry a man who can get and maintain a job. Is it?

I wouldn’t look elsewhere for salary alone, although maybe I should. What I’d look for is a job in product management, because that’s what I want to be doing anyway. I’d probably be able to at least meet my current salary at a more junior-level position and then work my way up. I’ve been extremely loyal to my company and I still am, but there comes a time when you have to do what’s right for your career. Eventually I want to found my own company and in order to do this I need to gain experience in a position closer to the product decisions. I should care more about salary, especially as a woman who believes in equal pay, but I don’t want to play that game. If my company believes I add value, they’ll give me a significant raise that’s fair for my supposed level. If they don’t, then I’m right to be thinking about what’s next.

The real reason I wouldn’t want to leave is that I believe my role does add a lot of value to the company, and I want this company to be successful. Yes, it will help my stock options actually be worth their “bonus” versus nothing, but there’s always an opportunity to leave, but there’s no better opportunity than now to really help the company do well in the context of my role. Maybe I’m giving myself too much credit, but I don’t necessarily trust someone from the outside to be able to come in and do my job as well as I do. In any case, I imagine if they were to hire someone for my position and require them to do all that I do they’d be paid at least $50k more per year. I guess that thought depresses me a bit. It makes me feel better to think of my current situation as being gifted a better title than what I deserve, and my pay is reasonable for the next major level down. I don’t like to think about salary as it just makes me uncomfortable — at the same time I feel like I’m being paid too much and not enough. I live a pretty simple life, in my small bedroom in my shared apartment, and I save… so ultimately that’s all that matters, right?

It’s just the way things are in business, I understand why so many women leave the workforce and don’t pursue executive positions. I look at my colleague who is about my age, in a similar position, and I can see him going on to be VP easily. I don’t see myself as an executive. It probably will take a move to another company to start feeling like one. Or maybe I’m just being greedy and I actually have a fair salary based on my title and level compared to others in the company. Only HR and the executive team know. I wonder what would happen in a company if everyone knew what everyone else was making, and raises were given for actual productivity and quality of work. I’m sure it would be hard to recruit non-junior employees, but it would be amazing for a company to offer salary transparency and also provide the opportunities to earn frequent bonuses and raises for the people who really deserve it.

I’ve been very fortunate in my life, having the chance to fall into career after career, and not go broke because of it. I don’t feel like I’ve taken great risks to get where I am, as instead at the time of any decision I always felt as if I was running from my past versus taking some great risk to reach some new level of success. I was, indeed, running towards something, but I wasn’t clear what it was or how to achieve it. So I led my life by proxy, making decisions based on what I didn’t want more than what I did.

And here I am, nearly 30, with a six-figure salary, a chance, if I get my act together, to become a serious technology executive, and enough stock options to potentially offer some cushion should my company continue to grow at its current pace – and even if they’re worth nothing, I’m carefully building my networth so I might be able to have some sort of stable future, especially as I venture to marry a man who has yet to save a penny, so I have to stop and allow myself to feel good about that.

Yet, this alone doesn’t feel like enough, however, because I have no idea how I got here or where I’m going. It’s a problem I’m lucky to have, indeed. But it doesn’t provide any answers. Lately I’ve had the opportunity to have a few significant conversations with people who are 15-25 years older than I am, and maybe I’m talking to the wrong people but they all seem somehow unfulfilled. Some are in jobs that they love, others not. No one seems to be happy in their marriages, if they happen to still be married. They all have kids, love their kids to death, but something else is missing.

How do I avoid getting to 45, just 15 years from now, and looking back wondering why I didn’t take the opportunity at 30 to start making decisions based on what I want, not what I don’t want. At some point everyone compromises. They marry the woman of their dreams to find out she’s a compulsive shopper and drains their bank account. They find a job that’s fulfilling but the amount of travel required puts a strain on their relationship, and the opportunity hey have to be around others who share similar interests makes adultery a tempting option, destroying an already broken marriage. Some are caught working jobs that they don’t love but that require the hefty time commitment otherwise, and they dream of a day when freedom will be possible, when they can run off and paint or write, though that time may never come, as responsibilities wear away at dreams, and they live vicariously through their children versus pursuing those dreams.

I know I need to do something soon to put me in the right direction. When I get antsy and confused I make poor choices throwing punches at time ticking on, hitting myself smack in the face and landing on the ground. I’m committed to my job right now, and for many reasons I enjoy it. But I also don’t see myself as a career marketer. So, despite my commitment, I need to plan my next steps. That is a horrific sentence. Planning takes clear goals, goals that I do not have. And what’s to say I’d pick the right goal anyway?

One thing I’m clear on is that many of my potential goals require additional training, and if I’m going to go back to school I’d like to do this before I have kids. If I am going to have kids, I’d like to have them before I’m 35. So, that leaves 5 years, at most, to apply to school, get in, go, finish, and have some sort of stable career started before having kids. And then, what if I want to take time off from the workforce, was all the planning and goal setting and schooling for naught?

I know I don’t excel when I feel like I’m drifting. I’ve got 2-3 years of drift wind in me before I get restless. Luckily in my industry things change quickly so I’m still very interested in the overall challenges we face, and I have a few new problems to solve. I just want to open more doors for my next opportunity, but I’m not sure how I can do that. I could potentially apply to school this fall for the following year, go to grad school when I’m 31-33, that seems to be a reasonable age to go, but is there a reasonable reason to go? Not sure. I’m confident I could spend the rest of my life doing PR. But then I’d probably jump off a cliff because I don’t like PR and I’m not that good at it as an introvert.

It’s time to make some hard decisions. In the next year I’ll likely be engaged, and I’ll maybe have an acceptance letter from a graduate program. Both of those options feel like the right ones. I am just unclear of the work required to get me there, especially for the school part.

My parents are what you would call lifers. They are not happy together by any means, my dad is a wreck and both verbally and emotionally abusive, and he will both talk to me openly about how hot some woman is and whether he should ask her out while also how much of an idiot my mother is, meanwhile, my mother has never been able to actually grow up in the relationship, she’s like a 12 year old who can’t handle the stresses of everyday life and is treated like such shit, but the two of them would never get a divorce. I haven’t exactly grown up with the best example of a good marriage to inspire me to walk down the aisle. Yet I still fancy myself in a white dress, signing my life away to one person, I’m just not sure why.

Financially, marriage is sometimes a liability. According to The Tax Policy Center, “Marriage penalties and bonuses result from the combination of progressive tax rates and taxation of a married couple as a single tax unit. With progressive taxes (which impose higher rates on higher incomes), combining spouses’ incomes can result in some income being taxed at higher rates than if spouses’ incomes were taxed separately. That can occur only if joint tax brackets are less than twice as wide as individual brackets. (A couple does not have to file a joint tax return but their alternative-filing separately as a married couple-almost always results in greater tax liability.)”

On this historic week when the right for gay marriage is front-and-center in the Supreme Court, I ask, why is marriage still such a desirable objective for life in the first place? Marriage was designed at a time when men basically owed their wives. Men also had mistresses and this was and still is socially acceptable in many situations (just not in the puritan US, but we still forgive.) Still, if a woman plans to be a stay-at-home mother, the tax savings for the couple are in their favor. “Couples in which spouses have similar incomes are more likely to incur marriage penalties than couples where one spouse earns most of the income, because combining incomes in joint filing can push both spouses into higher tax brackets.”

Meanwhile, I wonder if long-term love and commitment is for everyone. As my aunt puts it, these days you wouldn’t stay in one job for the rest of your life, why should you commit to one person? She believes, outside of the tax issues, marriages should be contracts for 10-15 years that can be renewed if all parties agree. I think that might not be a bad idea, but more so because when something is forever people become complacent, and relationships take work. If you knew in 10 years you had to renew your vows for your marriage to continue, maybe there’d be more focus on ongoing courtship. And if you happen to grow apart, then you can both move on without going through a nasty divorce that destroys your financial future.

From a sociological perspective, is committing to one person still relevant? I’ve recently had a few unrelated conversations, mostly with men, who discuss the idea of polyamory as this dream life that’s impossible with our current social constructs and state of jealousy. There are two issues at hand: one of the financial benefits or penalties of marriage, and then one debating the entire foundation of lifetime monogamy. One can not be married and still be monogamous and vice versa. Yet at the age of almost 30, in a seven year relationship, with everyone in my family breathing down my back about when I’m going to get married, it’s hard to just ignore them and do what’s right.

My boyfriend Derek* really wants to get married. I threw out the concept of a pre-nup the other day, which just felt like dirty conversation. I have $200k in savings, he has nothing, so my aunt thinks I’d be stupid not to protect myself should we one day get divorced. But if you think in your heart that there’s even the slightest change that marriage isn’t forever, why get married in the first place? What would be so wrong with just committing to someone, having children with them, and in all purposes living life like a married couple, just not being married. If for some reason 10 years go by and it just isn’t working out you can part ways, if not, you can stay together. Do we really need marriage to force maturity on us to get through some hard times together in order to see the light again?

I might get married. I’m not sure yet. My grandmother keeps saying my boyfriend needs to “shit or get off the pot.” And maybe she’s right. Maybe marriage isn’t so bad after all, if you ignore the tax penalties for a married dual-income couple. But I don’t want to turn out to be like my aunt, divorced at 49 after many, many years of an unhappy, unfaithful marriage, and I see others who are in similar situations around the same age.

I think these days people get to be 50 and once the kids are grown up, there’s no reason to stay in these types of marriages anymore. Even if these people would never be happy with one person forever because they’re addicted to the passion inspired only by novelty in a romance, they may be happier alone and always hunting than committed and never fulfilled. Usually, from my observations, these types of people also come from instable families, so they seek out such instability, it’s what’s comforting to them, whereas people who grew up in more stable households are more likely to have happier marriages. But even they may grow bored after a while. I find it odd that we expect people to go from dating many others in their teens and young adult years to dedicated to one person for the rest of their days. Other than for the benefits of raising children with two parents (which one can argue is not a full benefit if the parents are constantly fighting and unhappy) how can we in a modern society see marriage as anything more than a religious tradition?

Unfortunately in my case, the financial benefits of my relationship would be available now, in the past seven years, as my boyfriend hasn’t broken higher than $30k in income, while I’ve worked my way up to $110k. If we had been married for half of our relationship I’m sure we would have saved on taxes. Once we get married, hopefully he’ll have a career and make a reasonable income, which will just put us into marriage tax penalty land. So people say buy a house and have a tax write-off, but you’re still writing off taxes on your interest only, which is above and beyond the cost of the house. Something just doesn’t add up. If marriage isn’t for financial benefit, why should we aspire to get married?

This colleague is exactly my age, at my supposed ranking of seniority in the company (title-wise) and yet he has two direct reports. I, on the other hand, have none. And, as I told him, if for some reason we both had to leave our current positions today, he’d be set up for a VP-level role at another company (or at least one at the same level) whereas I’d have difficulty securing a position at my level due to not having direct management experience.

But that’s not the real reason I want to manage. I’m at a time in my life and career where I have ideas on how to move the needle that are bigger than what one person can do. I also want to learn how to be a good manager, but it’s so challenging as I wasn’t brought up in the most socially normal family and my general “how to relate to other people sense” is always lacking. I’m really working on that, and hopefully it shows. I figure I’ll always be ADHD and sometimes not think before I talk completely, but as long as I keep a positive attitude and am not afraid to be relentlessly enthusiastic, it will get me somewhere in life. Well, it’s gotten me where I am today to a point. Still, I’m no cheerleader.

I’m about 1/3 into Sheryl Sandberg’s book Lean In about women and leadership. The more I read, the more I relate to Sandberg. I think it’s because she comes from a typical Jewish second-generation immigrant family which lays on the guilt and criticism hard. She writes about when she was listed as #5 most powerful women by Fortune Magazine, ahead of Michelle Obama, and her very own mother said “I know you’re powerful, but do you think you’re really more powerful than Michelle Obama?” Our parents implant scripts in our mind about how we’re allowed to trust ourselves and our success. When you don’t feel like you deserve accomplishment you’ll never accomplish all you can do.

When I started managing at my current company I was told I would be managing the bosses’ sister. Luckily she was/is a extremely intelligent and hard-working woman. But her heart was never in the role that she was hired for, because it was clear she was being hired into a position for the time until an opening was available in the field she wanted to pursue. That in itself was not bad — sometimes having people with different experiences can add to a team, and she was amazing at organization and management of certain elements of my job that I just couldn’t handle with my own personality and work style. In many ways we did work well together. There were a few ways where I went wrong, and also where my company, you could say, did me wrong as a young manager. I was never told her salary, so for all I know she was earning more than me, and without knowing someone’s salary that reports to you, it’s hard to figure out how to motivate them over the long term. I also was learning a new space myself (it was my first straight-up marketing position to begin with, and first position in a non consumer company) so actually being a mentor in areas I was trying to figure out, even though my gut told me I had good ideas, was just not working. This, along with a short stint managing two Ivy-league interns with a chip on their shoulders, has led my company to put me in the “not a manager corner.” And I really don’t want to stay there.

I’ve written before about how “maybe I just don’t want to lead,” but that simply isn’t true. When I’m in my comfort zone — managing projects which I feel capable of performing myself — I love to manage. When I have someone working with me who is highly intelligent and motivated, or really good at a specific area which they are in charge of, I’m happy to let them run the show and motivate along the way. I’ve learned the hard lesson that it’s better to fail due to not having enough time to get everything done yourself than to delegate tasks to the wrong people. Failure is not the best either, but it’s better than getting yourself into a situation where you find it’s much easier to start from scratch then try to explain to your direct report how to fix things. Moral of the story, even with the world’s greatest team as a manager you have to delegate smartly from the get go.

What happened with my first and only real direct report was highly unfortunate. I watched our relationship unravel in just six months. Although I was a terrible manager, we accomplished a lot together for a small team. I wish there was a way I could have instilled more of that in my six months of supposed leadership. Instead, I had a frustrated direct report who wanted to do a good job, who was amazing at some projects, and not yet ready to work on others without someone who knew what they were doing teaching her at the same time.

I admit I also struggle with determining how much to “give” in the work world, and these days I’m leading to “a lot.” It’s very interesting, in Sandberg’s book she cites research that if a woman helps others professionally – men or women – they feel less indebted to her than if a man helps them, because women are just supposed to want to help whereas a man is going out of his way to provide help. I wonder how true that is. The book probably offends a lot of people because it calls out these stereotypes, but there is research behind them. There’s a whole chapter on “Success and Likeability” where she cites numerous studies around how women who are successful are seen as not likeable and women who are likeable are seen as less competent. There’s all these negotiation tactics that have been researched for women which basically say “you just can’t negotiate like a man because you won’t get what you want it you do.” Sandberg doesn’t want the world to be like this forever, but to get more women in leadership roles, she sees this as a necessary evil.

My greatest challenge then is how do I get over this fear of helping others succeed. Managers never do. I realize a lot of this is due to insecurity in my position and as I mature as a professional it will become less of an issue. But as a 29 year old person who is actually relatively senior in my company (yet managing no one directly) I find that I often am given the opportunity to help someone who is often older than me and usually male get the spotlight. When women have to fight so hard to prove their competence, it sometimes feels like you almost have to show that what you do isn’t easy, and have someone to point to in order to prove this. Which is terrible — it’s no way to manage or be a colleague, it doesn’t help the company, and it doesn’t help me in the end. It’s just frustrating that I feel like my boss only appreciates how good I am at writing (speed & quality) because he’s seen how hard it is to have anyone else do what I can do. That makes me more valuable to the company, but wouldn’t it be great if I could train more people to be able to do this?

Right now, I have the opportunity to both show my leadership and stop being so selfish in hoarding the skills I actually do have. One member of our team, who really should be directly reporting to me but isn’t, is a good writer but he’s struggling a bit with the business and product language, as well as the flow of overall stories. As my boss refused to have him report directly to me and and instead decided to take it on himself to be his manager, a part of me wanted the situation to fail, because I wanted to show that I’m actually suited to managing a person focused on content, an area where I’m actually competent. It’s not that my boss isn’t capable of managing him, but he doesn’t have the time to effectively manage either, and really for the sake of our team and the company he should be focusing on higher level strategic challenges vs the day-to-day management tasks that I really could do.

I guess I’ve given up at the idea of being given a direct report, and instead I’ve now decided that my wise-for-his-age colleague is right, the best way to become a leader/manager is to just be a leader/manager. At some point, I hope, this will be recognized and rewarded. If not, so be it. Ultimately, if I’m at a job interview and someone asks “have you managed anyone” I can make the choice to flat out lie or to explain that I’ve managed large external teams (which is true) and co-managed direct reports (which is also true.) I’m pretty sure this won’t secure me a VP-level position, but honestly if I’m going to get a VP-level position it will be for my skills of building a brand from the ground up, not because I’m the world’s most experienced manager. I need to look at my opportunities now as a time to learn how to be a good manager, so when I actually am one, I can knock it out of the park.

My aunt, who is a high-level manager at a media company, told me that managing is the hardest thing she has to do. “It’s really like parenting,” she says. And she should know as she has two young children. It takes patience, constant positive feedback, and carefully placed constructive criticism to encourage growth and improvement. Even that doesn’t always work. But you can do a lot by using the right tactics. That’s what I need to work on. Heck, even if I’ll never be a manager, I’ll one day — hopefully — be a good mother for it.