My 3-Steps When Making Big Career Decisions

Eva Gutierrez ✍🏼
Ascent Publication
Published in
3 min readJan 28, 2020

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Photo by Christin Hume on Unsplash

This week I came across two incredible career opportunities.

The first opportunity is to pitch myself to be the marketing director for one of my clients. They’re building their team from scratch and while working on their emails, I know that I can put together a marketing strategy that we could start implementing today.

The second opportunity is with a client who I just started working with, who intends to ramp up work, and—if I prove myself—give me more responsibilities in the future.

Standing at a fork in the road, an unable to take both options, I had to ask myself…what decision do I make?

Each decision is an incredible career opportunity, different in their own ways.

Here’s how I decided which direction to go.

1: Pro-Con List

So basic. So simple. And so to the point. The last time I used a pro-con list was when a past client offered to bring me on full-time (funnily enough, for the same positions that are available to me now). As a freelancer, full-time can sound like a dream. Steady pay, no contracts, health insurance?!

I stood at my whiteboard and wrote out the pros of going full-time with them and the cons. Quickly I realized, that the cons far outweighed the pros. While health insurance was certainly a luxury, I realized that I wouldn’t be happy in that position long-term.

And that’s what made me come back to my white board. I asked myself:

What are the pros of each job and what are the cons? Then, I give each pro and con a number from 1–10.

For pros, a 1 means that it’s a pro but it’s not so great and a 10 means that it’s an incredible pro.

For cons, a 1 means that it’s a con but it’s not terrible and a 10 means that it’s a huge sacrifice to what makes me happy.

Once I’ve given each pro and con a number rating, I’ll add up each column and see which has the highest “score”. If the pros sum to 24 and the cons sum to 32, then I know that the cons of the job outweigh the pros and strategically I can see which one seems to be the best decision.

2: How does this align with my 1, 5 and 10 year plan?

Now, I ask myself a strategic question:

How does this opportunity align with my 1, 5, and 10 year plan?

The opportunity needs to be helping me reach my goals and right now, it would be helping me reach where I would hope to be in a year or so. Then, it would be giving me the foundational knowledge and colleagues for where I want to be in 5 years, and it should be moving me in the direction of where I want to be in 10 years (although my 10 year plan is very vague, as I’ve learned things change quickly).

So far, I’ve focused my decision making entirely on strategy. In as black and white a fashion as possible, I want to be saying yes or no to each opportunity for a strategical reason—not an emotional one.

3. What does my gut say?

And cue the emotional guidance—what does my instinct tell me?

When I look at both positions, which makes me feel beyond excited to start? Which one can I not stop thinking about? Which one makes me think, wow, this is it?

In every case, once I’ve been able to strategically narrow down my choice, my instinct always starts talking. I start to feel a pull in a specific direction and I start to unpack why I feel pulled in that direction.

In this case, I know the potential one client has to have on my life, from career to my personal relationships, to my mindset. I respect what he’s doing and it’s a path I want to follow—so, my heart tells me: go left.

Incredible work opportunities are something I am grateful for. I am grateful for the opportunity but I’m really grateful for my ability to work through the decision making process without an irrational emotional tie to either outcome.

I want to make these decisions in a clear, focused, and strategic manner because that’s the theme I want to center around my career.

And this is how I’m doing it.

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