Romanticizing the Underdog No More: A New Approach to Turning 30

The other day, I was reading a blog post written by a 30-something about how being 30 means that you can no longer allow yourself to fail heroically. The author was not any 30-something 9-5 worker or woman spending her days sending out resumes while getting by on unemployment. The blog post was actually written by the beautiful, extremely successful Erin Foster, a television actress and writer on the site Hello Giggles.

Foster’s blog title sums up the feeling:

She writes in her post “Dirty 30: I’m Freaking Out” how she worries about getting her next written opportunity, about her next failure, even though she’s very successful for her age. “There is a period of time when we are allowed a free pass,” she writes. “We fail a math test because we’re in eighth grade and who cares. We sleep in until noon because we’re sixteen and just leave us alone. We get lazy at work because we’re twenty-three and it’s a job we aren’t passionate about. But at a certain point, we’ve run out of free passes and we have to be accountable for every single decision we make. There is no room for error. No one is asking you what you want to be, they are asking you what you are doing. Right now. What are you doing? Are you great at it? Are you making a difference? A lot of people are doing something important. Are you? Are you productive every day? Are you always working towards something bigger?”

Even Anne Hathaway, Oscar winner, who happens to also be 30, is quoted as saying she’s not impressed with herself, only what was created around her, and she constantly worries about where she’ll work next. “I’m still the underdog,” she said of her Oscar win. There’s something deeply romantic, falsely humble, and egregiously motivational about putting oneself in the bucket of never good enough which kicks our insecure yet confident asses into doing really great stuff. But it’s also kind of painful to the soul. It’s not a good way to live.

The thing is, once you hit 30 or near it (I’m the later case) you realize that life, despite not being able to be storyboarded and performed to perfection, requires some general planning and direction to get ahead. You can spend your entire life doing anything, and if it isn’t true to who you are, then you probably won’t be happy.

But then – especially for women – many of us have been trained into thinking that the only way to succeed is to just play the underdog role to the best of our ability. Confidence is needed, but not something we should seriously have. Guys can get away with being cocky, but that trait tends to be much more unflattering on a woman. And at 30, we’re really becoming women, which is still relatively new, as the 20s are a time when we’re in that transition between two major phases of our lives, and everything is so fucking confusing.

…I saw a quote on Pinterest yesterday morning: There are years that ask questions and there are years that provide answers. For me, 29 is the year of asking. It’s a necessity. For my readers who enjoy personal musings, you’ll be excited to know that the flow of posts will come more regularly, filled with questions. For those who expected quick tips to becoming a millionaire, you’re out of luck. I’ll post those when I’m a millionaire, but I’d bet that they won’t be “quick tips.” That is, unless someone accepts my bet, in which case I’ll suggest bet someone you can come up with five meaningful ways to quickly become a millionaire that actually work for you. Well, there’s one of them.

Everyone is on a journey in life. For some, their path is clear. Many are born wanting to be parents, or quickly discover their passions. Some, due to circumstance, have no choice in the matter. For those that do, the options can become overwhelming when such clarity fails to surface. But maybe that’s ok. I think there’s value in sorting these things out a little later in life. I’ve definitely gained maturity over the years, and despite still lacking confidence I find I’m more aware of the specific things that make me happy.

In order to really set out on this quest for happiness, I must discover myself. It’s a narcissistic journey in some regards, but narcissism is a human trait. Except for a few Yogis and Buddhas, the rest of us spend our lives first seeking how to be the best person we can be, then how to find the best person for us, and how to then pass on all of our learnings over the years to our children.

Setting out to make a lot of money is an easy quest, but if that’s not the primary goal of life then it takes time to determine what is and to creatively come up with the process in which to reach one’s goals. I feel like I’m just on the cusp of figuring that out, but I’m not quite there yet, and I need some collective wisdom to help nudge me in the right direction. I’m too scared to take any giant leaps from the security of where I am now, although I do feel finally ready and mature enough to spend time focused on one area, perhaps in graduate school, to really uplevel myself and my career. But doing what – that is the question.

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6 thoughts on “Romanticizing the Underdog No More: A New Approach to Turning 30”

  1. I think it’s okay for goals to be fluid, too – but it reinforces the fact that we’re constantly underachieving. I want different things now than I wanted when I was 25. And I might want different things again at 35. I think the mental leap is recognizing that we’re not falling short on goals (well, most of the time when we work our asses off), we’re just changing the finish line. And that can be okay too.

  2. Thank you for writing these posts. I connect to them!
    I’m in a similar position, of feeling scared, of wanting to achieve so much but feeling behind, feeling like the task is insurmountable. I feel paralyzed with the choices in life.

    I hear you when you’re worried about not being able to afford a house. I live in Britain (as a foreigner no less!) and it means I have to save 20% downpayment, and the only thing I can afford is a flat!

    Do I chase after the high flying sexy job? Or do I settle down with the amazing bf?

    It’s all exhausting, and this is where I can comfortable say. This is unhealthy anxiety you have in your life. Get a grip!

    About the feeling like the underdog. I’m really glad you’ve mentioned it. I feel in the past 6 months I’ve transitioned out of the underdog mentality as well. (I am now 30 as well! The magic 3-0 which brings on these anxieties in women). I am loving my new mentality now. I call it “Hit the ball out of the park”. It’s as if you’re running a 10k race. I want to finish the race feeling like I gave it my all. No matter where I finish, first place, last place, middle place I want to feel like I gave it my best shot. And it’s been an amazing change of perspective. I now walk into job interviews feeling like I own the job, I have a much healthier perspective when I get turn down (it wasn’t the right job for me). I bargain like my life depends on it and it’s now fun!

    I’m not saying the change in perspective eliminates the anxiety, but I think it’s all part of a bigger puzzle. Thanks for putting your thoughts online! Please keep on blogging this stuff! It what differentiates you from the other blogs I read!

  3. I wouldn’t say once you hit 30, you’ve run out of free passes and that there’s no room for error. It seems a bit harsh. When I was approaching 30, I was overanalyzing my life and comparing my life to everyone else who was around the same age. Now that I am 30, I don’t compare as much and focus on what I want. It’s weird, in the last year, it seems things got a little bit clearer as to what I want for the future. Like you were saying how the 20s were so effin confusing, just one big jumbled mess. I think that when you enter the next decade it starts to straighten out. At least I hope for most of us it would.

  4. It wasn’t very long ago that I turned 30 and I remember it hitting me hard. I looked at my life and from my perspective I hadn’t achieved all that I had wanted to by 30. I guess very few of us are actually happy with ourselves at 30. I hope that changes by 40!

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