2014: One of those Transition Years

My life is organically bipolar. Every 3-4 years there is a natural transition that by fate forces significant change. As much as I hate change as it’s happening, in the long run this makes my ADD self happier. I get bored living the same life for too long. I do my best work, and am my best self, in situations that are a month or so in from early novelty. So I should be looking forward to 2014, or at least 2015. It is clearly going to be one of these transition times of my life.

So why am I so afraid? First of all, it remains challenging for me to watch a business I helped build go through its own rollercoaster as a startup. I want more than anything to be 100% positive all the time, keep my head down, and help pick up slack where needed as our small team continues to shrink, but I’m lost in questions of how much professional value I get from going down with the ship, should it sink. Meanwhile, according to discussions with my boyfriend, 2014 is the year we supposedly get engaged. That’s something I’m looking forward to, though at this point, having dated nearly 8 years, I feel like we’re already married minus living together – and that too may be a change that happens this year.

On the career front, it was challenging to learn a colleague I respect has opted to move on to a new role. The move this colleague has made is smart for them and I wish them all the best, but it really puts a strain on our already small team. My boss is trying to spin this as an opportunity for me — X left the team and now you get to do all of those projects you said you were interested in doing — which to some extent is true. I can choose to see this as an opportunity to stretch myself and grow in my skills under the tutelage of a senior professional in my industry. However, I’m still afraid that my experience at this specific company, outside of wanting to stay and contribute to helping it become successful on some level, will not help me personally in my career going forward. I already know this as in my practice interviews I have been told repeatedly that the role has been given to someone with more enterprise experience. I think most people just don’t get what we do still, and the last thing one wants to do in a job interview is have to explain every single company on their resume.

The other thing is I really care about the people on my team. While before I could see my potential exit being a challenge to them, now they’d really struggle without me. What’s more, I know that in the next 6 months to year, if I choose to stay, then I need to be selfless, heads down, work long hours, get back into the super startup mentality, and make things happen. There’s certainly room for that. I just am unclear how much of my success will be reliant on things completely out of my control. Isn’t it safer to spend a year or two at a large enterprise, learn from the big boys, and just have a company on my resume that people understand?

At this point, I can see myself in the worst spot for future opportunities within my team should things take a turn for the worse. Most of my fellow team members already have deep enterprise experience and have resumes filled with companies people know of and understand. Another has a family business to return to when the time is right. I’d hope that if I am 200% in – no matter how things turn out – that my work and dedication will be respected and someone will help me secure my next opportunity. But my colleague, intelligent and talented as they are, didn’t choose to wait. Despite being the same age they are in a more advanced place in their career, yet I’ve always looked to them as a measure of the overall health of our business. So that’s something. They are going to do great things in their career, using this experience largely as a jumping off point, and the right time to jump apparently was now.

I just need to detach dreams of success from what I need to get out of this opportunity right now. What I need to get out of it definitely aligns with what’s best for the business, but I still need to convince my boss of this. And ultimately the amount of work is too much for our small team, we will have to prioritize tasks, figure out if we all work 14+ hour days, or select more strategically and stingingly to keep some time for our personal lives. We’re no longer that kind of startup, though, and we just don’t have that blood in us anymore.

Well, I’m still taking in the news that my colleague has decided to leave, as it’s not a surprise at all but it’s still yet another reality check. I’m unsure if I’m afraid or just upset. I’ve done some extra self reflection over the past few weeks and I really don’t have my heart set up on running a marketing organization, so maybe this is also an opportunity to reflect and, when the time is right, redirect my career. Maybe I should go be a photographer or study film. Or just get an MBA and have better options as a some-kind-of executive.

I wish I could share my struggles with my parents, but they don’t understand. My father doesn’t understand the odds of startup success, and thus, when he asked how business is going and I didn’t have the usual “great” answer, he started going on about how concerned he is. I just wish he could be proud of me for the larger picture — how despite my lack of clarity over what I wanted to do in my early 20s, and even still, I’ve managed to save a sizable sum, and, hey, I’m not living on the street. It’s funny, because when I think about leaving the world of enterprise software to do something more creative, like become a wedding photographer, the first voice that comes to mind is my father’s judging me for selecting a career where I’d make less money and be (in his mind) less stable.

I do like money, and it would be great if I could find a career which enabled me to be creative and also make money. I wish I had become a film director or cinematographer. I think I do have some talent in me in the world of arts that I have no time now to nurture, outside of my musings and rantings on this blog, which aren’t very productive. My boyfriend and husband-to-be is the complete opposite of my family, at least for now. If I want to quit my job and go become a circus clown in the middle of nowhere and live in a cardboard box he’d be completely find with it.

Of course, if we have kids, we’d want to figure out a way to make enough money to be comfortable, but he doesn’t care what sort of income we make beyond our basic necessities. So maybe I should take advantage of that. After all, who ever became successful in their creative endeavors without a little financial risk? It’s not like I’m risk-free at the moment… I make good money today but tomorrow could be out of work and back in a lower-paid position. There’s no such thing as a risk-free career anymore.

Who am I kidding, though? I’m not about to pick up and go to art school (and even if I wanted to I’d need a good year or more to put together a portfolio.) The smartest thing to do is to remain in marketing and just figure out how to provide the most value to whatever company that will have me for the given time. A positive attitude and a lot of getting stuff done will keep me employed enough to save money in between periods of unemployment. While I’m a bit depressed over the prospect of losing $20,000 thanks to my miscalculation of risk in early exercising my stock options, I need to put that behind me and just focus on the positives. Here I have an opportunity to really make a difference. I can pick up new skills and maybe even get myself to a position where I too can be an attractive hire like my colleague who has gone on to an extremely respectable role and likely an extremely respectable salary. Why can’t I follow that path as well? The only question I need to answer is – do I want to?


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2 thoughts on “2014: One of those Transition Years”

  1. Good luck. It definitely sounds like you’ll have a busy year and I’m sure some of the days will make you want to pull your hair out. My recommendation would be to take a look at this post every couple of months and compare how things seem to be going real time, and try to think “What does this mean?” and “Where do I see things going from here?” And in both cases, be honest with yourself.

  2. Hope everything works out for you. Sometimes we can try with all the good intentions but we may need a little luck and for things to go our way to achieve our goals. Hope for the best and carry on, I would say.

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