Hard Decisions Become Easy When You Do This

4 Ways to Gain Clarity When Opportunity Knocks

Image: 傅甬 华/Unsplash

Last week, a friend had a job offer come up. It was a stable job opportunity in a chaotic time. It would be a step up in his field of work, it promised good money, and it could open up very interesting doors.

He also experienced high stress while interviewing for the opportunity, he wasn’t sure about this specific career, and he wasn’t desperate for the money. 

He wasn’t sure yet about what he should do.

He called me because I was in a similar situation just a year and a half ago. Long story short, I decided to take on a big work contract. I was lucky things unfolded the way they did, but I should have known how to make that decision more deliberately. 

We chatted for an hour or so. I talked about my experiences, and almost started wandering down the path of what I’d do in his case. Then, I smartened up. 

In my note-taking system, I started a thread about how to make difficult decisions. I ran to get it, and read the notes in it to my friend during the call.

A few days later, he texted me and said he knew what he needed to do, and that our call gave him a lot of clarity into his situation. 

I was happy. I wrote the thread for myself, and I knew it would be useful for him, but didn’t realize how clarifying it could be. 

Here’s what I’ve written down in my notes, and what I told him:

Define the Important Areas of Your Life

I really like Skillshare and Otis founder Mike Karnjanaprakorn’s post on setting goals. The short of it is, he defines the areas of his life that are important to him, and sets goals he wants to achieve. Each week, and quarter, he checks in on his own progress.

The key to this is not just in the goal-setting portion, but actually in quarterly and weekly reviews. Are you actually making progress on those goals? What are you doing that’s working and not working?

In my experience, setting the initial goals can take maybe even less than an hour. The best way to come up with the best answer you can in that moment, then think and improve it the next quarter. Goals and plans are guesses, and you can always improve them. This way, whenever you check on your goals, you have the best version of them.

These goals will determine what you want your life to look like, as well as how you evaluate your opportunities. If, for example, my friend was interested in mental health, he’d consider that the interviewing process created a stressful experience for him. He might consider whether or not it was indicative of how the job would be, and decide deliberately whether or not it was worth it to him.

Define Your Anti-Goals

Metalab and Tiny founder Andrew Wilkinson writes about the power of knowing what you don’t want to do. He figured out what he wanted his days to look like by calling out the things he didn’t like (e.g., long meetings, packed calendars, etc.).

Back to my friend — he could quickly list the worst parts of his days. Or, if he wasn’t sure, he could look back at the worst 5 days of the month (or year), and see what they had in common. 

For example, if he hates meetings as much as Andrew does, and the job clearly requires a lot of meetings with stakeholders, etc., then he’d know this opportunity might not be worth his time. On the other hand, if there were no meetings at all, then this opportunity could be interesting. 

Work Backwards from the Future

In 2013, Pixar set a goal to make their movies cheaper and faster. On average, each movie cost them 22,000-person weeks, and they wanted to bring that down to 18,500. In Creativity, Inc., Pixar co-founder Ed Catmull shares how he prompted his team for suggestions: 

“The year is 2017. Both of this year’s films were completed in well under 18,500 person-weeks. … What innovations helped these productions meet their budget goals? What are some specific things that we did differently?” 

It’s a simple prompt, but one that I really like. They forecast the setting four years later, and ask for suggestions on specific things done differently. Without a realistic way to get there, a vision remains little more than just that. It won’t become reality.

If my friend had defined his goals, he could use this to determine how to get there. He’d have an idea of whether this opportunity sets him up to achieve his goals, or takes him further away.

Assess the Current Situation

Ryan Holiday asks, what’s the absolute worst thing that could happen? What would you miss out on if you did it? 

The answers need to be clear here. If they’re not, go ask someone who has either done something similar, or knows someone who did. Ask them what happened with the decision and what the outcome was. Or, go read a book about it. 

And as Ryan advises, most people can’t see your goals and vision beyond their own experiences. Don’t outsource your decision-making to them and ask, “What would you do?” They’ll give you an answer for what they’ll do, which they might position as what they would do if they were you, but neither is the same answer as what you should do.

I emphasized this to my friend, calling myself out, cognizant I might’ve biased him towards one decision or another. (Of course I had an idea what I would do in that situation, but that doesn’t mean I knew what was best for him. There is a subtle, but very important, difference.)

Clarity Makes Hard Decisions Easy

If there’s a common thread in all of these exercises, it’s that they clarify your goals, desires, and enable you to put a plan together for yourself. Whenever an opportunity comes up, you at least have a destination you’re working towards. 

From there, it’s just a simple matter of figuring out whether the opportunity supports you to getting closer to it, whether you can finesse it into such a vehicle, or whether it’s a trap — a swamp that will keep you stuck, forcing you to chase something you didn’t want to in the first place.