New Career Goals

Betsy Freeman
3 min readJul 15, 2019

I would pay good money to never be asked again “What’s your 5 year plan?” Similar to my signature when I’m checking out, I scribble a smiley face and bounce.

The previous generation is not known for loving their jobs, so they rocked us to sleep telling us to achieve our dreams, save the world, and have a better life. That’s a lovely sentiment, but also an incredible setup for high pressure. What if that job is not dreamy? What if there is no trajectory to ever breaching into that first triple figure salary? What if you can’t pay for ramen or much less rent while lending a hand all day to others? Surrounded by other’s horror stories of life regrets, we must make a plan for success. Break that plan down into goals and stardom could be yours, right?

Goals can be very effective, but also highly constrictive. The key to successful goal setting and achievement lies in broadening the end goal to your values and priorities. Focusing on just career titles and achievements is too narrow.

“Write your eulogy not your resume.” That snippet I heard in a speech by David Brooks, a New York Times columnist, is perhaps the best advice I’ve heard when it comes to career goal setting. Start with your bigger picture goals and priorities for your life and quit with the titles. At the end of the day, what do you want to be known for? What is success in your eyes? As selfish as it sounds, it’s true that the only truly successful people are people who think they were successful.

These conversations are great to have with yourself and your journal, but it is crucial to broaden your perspective by bouncing these questions around with others who have similar values and better yet, are further along their way. They may have insights as to where you are being short-sighted. Added bonus is asking someone who knows you well. Said person may help you sort through your thoughts and keep your goals authentic to your identity.

After your mountaintop time of asking yourself existential questions, it’s time to get tactical. Start to work backwards and towards a certain kind of specific: what kind of lifestyle do you aspire to have in the near and far future? Wealth — sadly, but truly — can solve quite a few struggles, but is too broad. What is it that you think wealth could afford you: flexibility? Taking care of expenses for your family? Lending a hand to others? An early retirement? Breaking down your greatest priorities and values gives you a platform to start to weave a more flexible and creative framework rather than pass/fail rigidity.

There are many ways to reach your goal destination, so when things are not working out as planned, remember you are not failing. Rather, you are exploring, riding, living. This paragraph is all inspired by a very recent unexpected life switch for me. I was zeroing in on step 3 of 10 of my perceived career ladder and I hit a wall. Stuff wasn’t panning out; what I wanted wasn’t available, and what I was doing was boring me to tears. I felt stuck and lame. Why did everyone but me have awesome careers going? (Not true, but you know how this sort of feeling if you’ve ever ached for something). Randomly an opportunity came up that was 4 steps to the left. A sort of trapeze vs. a ladder. Stricken with relentless curiosity, I went for it, and I’m telling you it’s been the best thing that ever happened to my career situation. I didn’t know what I didn’t know, and it took something from left field to help me tap into a side of my skills and passions that I didn’t even know existed. However, as much as this latest step has been unexpected, it was a successful move because it lined up with the scheme of my greater goals.

In summary, goals are good, but maybe need to be reframed from their classic definition. Get to know yourself, stay engaged, stay curious and enjoy your own path. Step by step goal plans sound like an endless step-master workout. I would way rather go on a run in the woods.

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