How to Make Fulfilling Decisions

Tutti Taygerly
Aug 6, 2020 · 7 min read
Man in a white room surrounded by numerous doors & window openings
Photo by Jan Genge on Unsplash

Last week I had to make a decision about taking on a product & design role for a well-respected coach to help him work on his company and their coaching app. It’s been a year since I left product design leadership at Facebook. While I’d coached many people over the past ten years, I’m now a full-time leadership coach running my own business. This opportunity and decision-making put me right back into a familiar space of having to make what felt like the agonizing decision of “Do I take this job?”

Looking back through my career, I’ve made this decision 15 times. My typical thinking, brain-first method is to figure out what I want from my next role and how well this opportunity checks those boxes. I create a pros & cons list. I consult with several close friends and family members.

This time was different. I took the time to slow down, connect with myself, and deeply understand what really matters to me. I got coached by several talented people in my community as well as my formal coaches. I tried not to stress out too much about it, and even after making the decision, to be OK with the tension that still remained.

I’m sharing a 7-step framework for how to make fulfilling decisions, incorporating both head and heart, and with plenty of room for whitespace.

1. Envision the future

Think about your particular decision. How long into the future would you need to see clear results / outcomes from the decision? Perhaps it’s 3 months or 6 months into a new job? Perhaps it’s one year after launching the MVP (minimum viable product) for your startup? Pick that amount of time and envision what your life would be like after the clear result of your decision. Some people can dream and imagine the future while doing something else such as taking a shower, a hike out in nature, or drawing / sketching / coloring. For others, it’s helpful to journal. Part of dreaming and creating this north star involves speaking it aloud as if it’s already happened.

Here’s part of mine:
It is February 2021. My business is doing better than ever. I continue to support powerful leaders in 1–1 coaching, group coaching, workshops, and speaking engagements. I am able to impact a large community with the products & programs that I create. I’ve also experimented with many programs, products, partners— some have worked, some haven’t, and I’ve learned from all of them. I’ve successfully integrated my product building skills and my coaching skills to continue my journey of exploration.

2. 10/10/10 Perspective

When you have to make a particular decision, it can seem like a giant black cloud, crowding out all other thoughts, with its rain threatening to soak through every single part of your life. One useful tool is the 10/10/10 perspective. How are you going to feel about this decision in 10 days, 10 weeks, or 10 months? This perspective helps give some space & time to the urgency and importance of this rain cloud. Perhaps it’s a giant decision that will matter a lot in 10 years, such as deciding to have a child. Or perhaps the decision isn’t all that important… it feels really important right now, however in 10 days it won’t matter at all.

You can also play with the unit of time. Perhaps 10/10/10 stands for 10 weeks / 10 months / 10 years or it could be 10 minutes / 10 hours / 10 days depending on what the decision is.

3. Space to say Yes and say No

Consider your options. When you say yes to this decision, what else are you saying no to? Or vice versa, when you say no to this decision, what else are you saying yes to? Come up with as many list-y items as you can. Rather than a pure pros/cons list, this ideation lets you play with all the facets that are important to your life and work. It can start to show interconnected threads or themes. It also helps with a clear sense of prioritization, and mitigates any positivity or negativity with the decision. Saying no doesn’t have to be a negative / failure / a dead end option, because it enables you to say yes to other things.

4. Ask your voices

The psychologist Edward de Bono outlined the concept of Six Thinking Hats where in every situation, you put on one of the six hats to approach the problem in a new way. Often while in a meeting setting at work, we would assign specific hats to individual people to play the perspective of that particular hat. The six hats are:

  • Blue: big picture & overall goals

For the decision, you can ask yourself what would each hat (or voice) have to say. Feel the particular hat and perspective. Learn from its opinion and hear them all out before you make any decisions.

Another way to look at your voices is seeing what your self-critical or self-sabotaging voice says. Perhaps it’s a voice of fear that says you’re not good enough or that you don’t deserve the job. It’s important to label this voice and call it out for what it is— a negative perspective that is telling you lies. A different voice to listen to is that of your inner leader or sage¹. This is the part of you that is calm, peaceful, full of positive emotions and wisdom. This voice knows how to make decisions and has done so in the past. What is this voice telling you?

Asking your different voices activates different areas of your brain and allows for a variety of perspectives and inputs into the decision.

You can also ask your friends to be different voices for you to gain additional perspective. Keep in mind that they will each bring their own biases and opinions to the decision. It’d be useful to pick friends that truly have your best interest in mind.

5. Whitespace

With all of these inputs, divergent ideas, and options on your decision, sit still and do nothing for some hours or days. Stop working so actively and trying so hard to push the decision into being made. Instead, simply go about and live your daily life and work. Think about the decision and all the options before you go to sleep at night. See if anything pops up.

We are often so active and driven to do things, solve problems, and progress forward with tasks and decisions. Giving even a tiny bit of whitespace to allow yourself to simply stop and be with the unknown space before the decision will open up some new insight.

6. Trust your intuition

Near the end of my decision-making process, I talked to one of my best friends about this product & design role for the coaching company. With unerring logic and deep love, he told me that it was a complete distraction from my long-term goal of building a coaching business. When he spoke the words out loud, I knew that he was right. It didn’t make any logical, rational sense. Simultaneously, I also knew that I wanted to take the role and that it was completely right for me. Both things could be true. My head said that it didn’t make any sense, yet my heart yearned for the connection to design, to making things, and to an exciting new mentor and opportunity to co-create.

I told him: “Yes, everything you said makes complete sense. And I’m going to take this role anyway. Because I want to.”

Ultimately, trust your gut. Listen to what you really want. Listen each morning to see if the thing you really want is still true.

7. Aftermath

Even after the moment you’ve made a decision, there’s still extra details to consider. These details are what remains to be figured it out. For a job, it could be things you negotiate— the title, the salary, responsibilities, and agreements about how you will show up. For another decision, it might be the boundaries and constraints you need to put in place to truly be happy with the decision. It’s important to make sure you have a good grasp of these details and agreements.

After the details is the aftermath. This comes after you’ve signed the paper or verbally committed to someone. Take a moment to consider how you feel. Is there relief? Disappointment? Tension? Excitement? Fear? Self-doubt? Or some combination of all of them. It’s OK. Sit with the emotions and recognize that you’re a complex person. It’s OK to feel all these things and still know that you’ve made the right decision.

My Decision

I ended up co-creating a product & design advisor position part-time. It enabled me to focus the majority of my time on my coaching business. Yet it also gave me an avenue of experimentation with a new partner relationship, access to intriguing content, and a wonderful way to integrate my past product skills with my current coaching skills.

I used many parts of this framework to make my decision and also set clear boundaries & agreements for how the position would look. Having a framework that integrates head, heart, and whitespace in decision-making only leads to more fulfillment.

¹The concept of saboteur and inner leader is taught in the Co-Active Insitute coach training program. Saboteur and sage is from Shirzad Chamine’s Positive Intelligence research

I’m your host, Tutti Taygerly. I’ve spent 20+ years in product design & technology, leading teams at startups, design agencies, and large tech companies. I left Facebook in summer 2019 to focus on leadership coaching full-time. I write weekly about topics related to design & coaching.

The Startup

Get smarter at building your thing. Join The Startup’s +794K followers.

Sign up for Top 10 Stories

By The Startup

Get smarter at building your thing. Subscribe to receive The Startup's top 10 most read stories — delivered straight into your inbox, once a week. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Tutti Taygerly

Written by

Leadership coach & champion of difficult people; designer of human experiences; ex-Facebook; surfer, traveller, mom; tuttitaygerly.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +794K followers.

Tutti Taygerly

Written by

Leadership coach & champion of difficult people; designer of human experiences; ex-Facebook; surfer, traveller, mom; tuttitaygerly.com

The Startup

Get smarter at building your thing. Follow to join The Startup’s +8 million monthly readers & +794K followers.

Medium is an open platform where 170 million readers come to find insightful and dynamic thinking. Here, expert and undiscovered voices alike dive into the heart of any topic and bring new ideas to the surface. Learn more

Follow the writers, publications, and topics that matter to you, and you’ll see them on your homepage and in your inbox. Explore

If you have a story to tell, knowledge to share, or a perspective to offer — welcome home. It’s easy and free to post your thinking on any topic. Write on Medium

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store