TIPS FOR MAKING TOUGH DECISIONS

Confession: I am not always good at making big decisions.

Many of the answers to the biggest questions I’ve ever asked myself have come to me intuitively, which meant that I really didn’t need to decide, because I just knew.

When I adopted my first pup, I wasn’t looking for a dog. In fact, I’d just said to a coworker the week before, “It’s amazing to me that single people get dogs, because I imagine that they really inhibit your freedom!” I was single. And precisely one week after saying this, I had a dog.

I had been picking up two friends’ dog from doggie daycare when I saw his face on a crumpled up flyer, taped to the front counter. As if the words had come to me from somewhere outside myself, I asked if I could meet him. When I met him, I knew on an intuitive level, long before I knew on a conscious level, that he was my dog. There was no decision - just a deep sense of knowing. When my friends arrived to pick up their dog, there were two dogs, instead of one. My friend just looked at me with a knowing smile.

The same thing happened the day I put in my notice at my job. While I was sitting inside of an office, there was a moment in which I swear I saw the clouds part and a big ray of light shine through, at which point I said, “my last day will be May 1st.” Once again, there was no decision -  just a deep sense of knowing, and the words came out of my mouth from what felt like a source greater than myself.

All of this clouds parting, light shining through, voices from above type of clarity is great, but it means that decisions can be incredibly challenging for me when this isn’t present. In the rhythm of normal work and life, it’s not always possible to wait around for this moment of instant clarity to strike. There are timelines and deadlines and normal life constraints that aren’t always conducive to waiting for an answer to appear.

In these situations, I often use a variety of tools and systems to explore the different possibilities at hand, to help lead me to the best decision based on the information I have at the time. Here are a few of my favorites.

GROUNDING…

CONNECT TO YOUR HIGHEST SELF.

Who are you when you are at your best? When you are operating from love, versus fear?

Connect to that version of yourself. And then, consider: what would she do?

EXPLORING…

TRY ON THE DIFFERENT OPTIONS.

Imagine yourself in the different scenarios at hand. For example, if you’re considering whether or not to leave your current job, you might imagine yourself staying in your current job, and leaving your current job.

• What does each option feel like?

• What do you see in each of these scenarios?

• What is happening, and how do you feel?

And then, after exploring options A and B, push yourself to think about a third path. Is there another option C that could exist that you might not have thought of before? For example, pursuing your passion as a side hustle while staying in your current job? Or, exploring a role change within your current company? Try each of these on as well and notice what emerges. Pay extra attention to how you feel as you sit with each one.

WRITE TO YOURSELF.

Write out the question you’re currently considering, and write out whatever answers come to you, without filtering or judging the responses.

For example, you might write: “what do I really want?” and then allow yourself to write down whatever comes to you as an answer. Write down whatever comes up, without thinking about it or filtering it or wondering whether it’s real or not - just write it down.

Then, when you’re finished writing, you can go back and revisit what you wrote. What do you notice? What are you surprised to see on paper?

Often we know more than we think we do, if we get quiet and tune in.

CHECK IN WITH YOUR FUTURE SELF.

This is the version of us who is 5, 10, 20, or maybe even 30 years older. This process involves consulting our older self and asking about the questions that are are pondering today.

• What path did she pick?

• What advice might she give us knowing what she knows now?

• What decisions led her to where she is today?

WRITE OUT THREE DIFFERENT LIFE PLANS.

Write out three possible paths for your life, in 5-10 year chunks.

• Path 1: the path you’re on right now.

• Path 2: a slightly modified version of the path you’re on right now.

• Path 3: an entirely different option - or the “if anything were possible option.”

Check in with each of these three paths. Which one feels most alive? Which one feels most aligned with your values and goals? Which one gets you most excited?

And, what is one small step that you could take toward the path that speaks to you most?

NAME THE GREMLINS.

What gremlins and saboteurs are present? Write them all down. For example: this could go terribly wrong. You might run out of money. This is impractical. Do you know what you’re doing?

• And then, consider: what, if anything, about each of these gremlins is true?

• What, about each of these gremlins, can I let go of?

• And how can I put a plan in place to prepare for the parts that are true?

“Be aware that whenever people take initiative to change their lives, an alarm sounds and the saboteur will awaken.”

- Kimsey-House, Co-Active Coaching

WHAT’S THE BEST AND THE WORST?

For each path you’re considering, write down:

• What’s the best that can happen (if I do it)?

• What’s the best that can happen (if I don’t do it)?

• What’s the worst that can happen (if I do it)?

• What’s the worst that can happen (if I don’t do it)?

Notice any themes within what you write.

For example, I often find that “the worst that can happen” is often logistical in nature—which typically, can be easily solved.

would i have been excited to seek out this opportunity on my own?

Let’s say that you are approached about a job opportunity, and the opportunity comes as total surprise.

Oftentimes it’s easy to assume that we should consider it, because it came to us.

But if it wouldn’t have come our way, would we be excited to seek it out ourselves? This question is often telling.

Just because something comes to us doesn’t mean that we have to consider it. This includes a job opportunity, an invitation with a stranger who wants to “pick our brain,” or a request to sponsor a cause that we don’t align with.

TAKING ACTION…

DECIDE ON A FIRST SMALL STEP.

Often big decisions feel overwhelming. If we are considering whether to leave our job, for example, a number of fears and saboteurs often kick in - What if we don’t find anything better? What about the benefits? What if we realize we made a mistake?

The first decision might not actually be to leave your job. It might simply be to update your resume. What if you start there and take some of the pressure off? Usually the first small step can be done without a lot of disruption and under the umbrella of security and safety of our current context, and is much easier than we think.

HAVE A BACKUP PLAN.

How can you move forward, while also creating a sense of security? This could include:

• Giving yourself a financial runway of three months to try something new

• Putting some money in a secret bank account that you can use if things don’t work out

• Getting a part-time job while you build your new business

• Taking a contract job (versus a full-time role) so that you can try things out for a year

• Signing a short-term lease

Having a backup plan allows us to move forward while also feeling safe, in case things don’t work out as we had anticipated.

CONCLUSION & RESOURCES

I hope that these tools are helpful for you in your own decision-making process.

Here are a few additional resources that may come in handy along the way, as well:

• Decisive: How to Make Better Choices in Life and Work by Chip and Dan Heath

• The Crossroads of Should and Must by Elle Luna

• Designing Your Life by Bill Burnett and Dave Evans

• The Ghost Ship that Didn’t Carry Us by Cheryl Strayed

Good luck as you ponder the big decisions you may be facing right now. Want some help along the way? Please feel free to reach out to explore how we might work together throughout the process.

“Once you make a decision, the universe conspires to make it happen.” Ralph Waldo Emerson

This post was originally published in 2019 and was updated in February, 2023.