Yesterday evening I met up with a friend of mine from jobs past for an insightful chat over tea. He’s one of my few friends who is also a professional in the technology industry, so it’s always good to share stories and dual-crowdsource our own advice. One of the themes of the conversation this evening was defining success, and the reason behind what makes those definitions so different for each of us.

My friend, we’ll call him John, is very analytical in his approach to happiness. He buckets each area of his life – career, romance, friendship, hobbies, and keeps a mental tab on the progress he has made in each of these areas. He is completely satisfied working a 9-5 job, as long as it’s stable. Working for a large tech firm, he’s accepted that churning out materials is more important than perfection. He enjoys the work, but isn’t personally invested in the success of the company. Today, he is extremely satisfied in his career progress, and he wants to focus now on developing his romantic relationships, since that area has suffered in the past decade when he earned two graduate degrees, including, most recently, an executive MBA.

I shared with him that I can’t imagine not being personally invested in a job. Being personally invested in the success of the company helps me focus and ultimately provides meaning to my life. Sure, having a small amount of shares in the company adds to that commitment, but the more important piece is being part of a small team where my daily work clearly makes a difference in the overall success of the company and everyone involved in it. That’s what I love. He called me ambitious and said that was a good thing, but mentioned he enjoys that he now has an MBA and fits in at the large company as a product marketing manager. He wouldn’t want to work for a company requiring him to give up his personal time, and he didn’t have a burning need to shake things up anytime soon.

So then we got into discussing what makes us different and why I’m so obsessed with working for small companies, motivated by instability, while he is the exact opposite, being driven by feeling secure. The difference, we discovered, was that he has already achieved his professional life goals: obtain two graduate degrees – check. He feels successful where he is now. Eventually he’d like to become a more senior manager, but he’s content being paid a f1000 marketing manager salary, and he enjoys being personally detached from the firm. I, on the other hand, don’t have a check list for my life. In fact, today my life goals are less clear than they were when I was in High School. Nothing makes me feel satisfied and proud of myself. He asked me what would. I said, I don’t know. Even if my current company were to have a successful acquisition one day, I wouldn’t feel a right to ownership of that success because I wasn’t directly involved in creating the product. The rational goal for my life should be to work towards a VP of Marketing title at a large corporation, yet that success wouldn’t make me feel satisfied. Maybe the check on my success list would fall next to the words “found a company” or “make a profit from a company that I created.” Only then will I be able to accept myself as a success.

But then, when I think ahead to the next 10 years, I wonder if that will even be true. Do I really want to found a company, or maybe what I’m really longing for is to found – a family. I’ve spent so much of my life trying to somehow prove myself and my talents to my parents (who, by the way, don’t understand or value the work I do), and I’m tired of wanting to impress them and never feeling good enough. That has tainted my opportunity to feel any sort of consistant happiness. I’m not so odd, I guess, in that I might just want a nice life with a nice house and 2-3 kids that I drive to dance practice. Maybe, after 29 years of thinking I would only be happy with being impressively different from the average American, the reality is I want nothing more than to divide myself by the population and find my life story square in the middle of it.

In my last post, a few of my commenters mentioned that in order to determine how to rebalance my portfolio I need to figure out what my goals are. Do I want to buy a house? Do I want to retire early? Will I have kids? By figuring out my goals, I then can plan my new portfolio balance accordingly. But I don’t know what I want. The easiest answer — the one that I can clearly see — is the life I live now, just older and a little wiser. I can’t envision myself as a mother with kids in a nice house, kindly yelling at my son to do his homework before bed and for my daughter to get ready for school. Is that who I am? A mom?

I’m more a mom than a VP. That’s likely because I grew up with a stay-at-home mom in the house and had very little understanding of my dad’s work, other than that it  had something to do with math and employee benefits. I understand how to be a mom, and have grown up making a checklist of how to be a good parent in the back of my mind, which is maybe the only life checklist that I actually have where satisfaction can be achieved. But if I am a mom, if my happiness is not focused on career growth, but instead domestic nurturing, I am completely lost as to how to map my daily tasks today to that goal, other than save as much as possible before making that transition. I just don’t want to work towards that only because maybe it isn’t what I want. I’ll get restless at some point and want to go back to work. Or maybe I won’t be able to have kids anyway. Becoming a VP is in some ways easier to plan – study for the GMAT, score well, get into a top MBA program, perform well in school, get a senior-level management job, and work my way up to VP. If I really wanted that, it would be possible.

If I really want to be a mother, how do I get there? If I want a nice house and financial independence so I can work as a part-time consultant from that home and still be the mom I might want to be. That seems much more impossible than the VP plan. I’m so far away from having enough money to own a house here. $200k, which includes my retirement funds, is nothing. My real goal, then, is $5M by 40, with a $1.5M house and enough cash left over to decorate it to my tastes. My then-husband and I would have enough money to take yearly vacations with the whole family to exciting locations without having to worry about killing our bank account. Ok, so my real goal is to be wealthy. $5M by 40 is not realistic. There’s a small, teeny tiny chance that my stock options could be worth that much one day, but that’s the only possible way to my goal, unless I actually do start a business and sell it for a profit. I feel like without the success of my current company, I should avoid being a mother and just focus my life on my career. I clearly have too much riding on this. In fact, my company stock, as exercised today, is 10% of my total networth. One of the reasons I take so much risk in the rest of my portfolio is that I want to believe that if I work extremely hard for the next 2-5 years, this will be my ticket to everything I want: a happy marriage, a nice house paid outright, and financial independence.

But – I need to plan for the worst case scenario. Five years go by, I’m 34, and my stock is worth nothing. My networth has shrunk due to having kids, so I can’t save as much as I have been saving, and the stock market crashes again. I’m stuck at $200k in networth, or less. I’m not at all closer to any of my goals. I then have to decide if I want to move to a place where the cost of living is cheaper and get a job that I likely don’t like, or stay and raise a family in a small apartment, moving occasionally when rents increase too much or the landlord kicks us out.

My goals, then, are to set myself up with as many routes to $5M as possible, while preparing for a middle class or lower middle class lifestyle. I’m not sure what to do, as the $200k still feels like nothing, when my entire networth in its entirety is not even a 20% downpayment on a standard house here. Am I so wrong to feel this hopeless, yet hopeful all the same?

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