Step-by-Step: Explore What Success Looks and Feels Like

Describing the “feeling” of success is difficult in a world driven by measuring outcomes. 

It’s no surprise we have a hard time articulating our feelings considering how we greet each other. When we ask others how they are doing, the expected answer is, “I’m fine.” People say this even when they are not fine. The range of feelings that society has deemed as acceptable is limited. People also say,” “Good,” “Not so good, but that’s okay,” “Tired” or “Busy” to indicate how much work they have. Some will say, “stressed,” which is understood that “stress” most likely refers to work stress.

Sometimes, it can help to talk through what success means with a friend. To start the new year, I wrote an essay suggesting we reframe the question, “What does success look like?” into “what does success feel like?” Other ways of describing this framing are like asking  “what do you do?” Instead of  “how do you do it?” It’s the difference in  “doing” versus “being.”

Because I enjoy learning with others, I developed a workshop for individuals wanting to answer these questions for themselves. I explain the framework and then take people through three rounds of self-reflection and partnered reflection to clarify their ideas.

Those who are visually oriented may get together with others to create vision boards. This exercise is oriented for those who prefer to express themselves with the written word.

Describing Feelings 

Writing down what success looks like is often easy for people, yet articulating what success feels like is much more difficult. In my workshops, I’ve seen people describe feelings as “stable income” and “good speaking skills.”

Feelings are abstract and it can be a challenge to describe the abstract. When I see a vision instead of a feeling, I clarify by asking a series of questions to help people get to describing a feeling.

For example, someone once wrote “Getting things done.” 

Julie: What does that mean?

Participant: I like getting things done.

Julie: What is it that you like about getting things done?

Participant: That things are settled and I don’t have to worry about it anymore. I can feel good about finishing.

Julie: Does that feel like ‘accomplishment’? 

Participant: Yes!

Sometimes I suggest a feeling, sometimes a person can get to the feeling on their own. 

Here’s another example in which someone wrote “high income” as a feeling of success.

Me: Why is it important to you to have a high income?

Participant: I don’t want to worry about my ability to take care of my family.

Me: Why is that important to you?

Participant: Because feeling anxious gets in the way of feeling good.

Me: So what does a high income represent for you?

Participant: Security. I want to feel secure. 

The DIY Version 

Here’s how you can conduct this exercise yourself with another person or a few other friends. You don’t even need to be in-person or on video conference. A phone call is fine. 

Round 1. Write down 2-3 ideas of what success looks like in your personal, professional and/or community life and then write down what you need to do to achieve each vision of success. Then share those ideas with your partner. Ask: Why does that vision of success matter to you? Why do you think that’s what you need to do to achieve that? Are there other ways to achieve those visions? 

Vision: Run a marathon

To Do: Find a training program I enjoy to get stronger at running

Round 2. Write down 2-3 ideas of what success feels like in your personal, professional, and/or community life and then write down what you need to avoid doing because it would prevent you from achieving that feeling of success. Then share those ideas with your partner. Ask: Why does that feeling of success matter to you? Why do you think you need to avoid those activities? Are there other activities that are preventing those feelings?

Feeling: Energized

Avoid: Boring, tedious activities

Round 3: Compare what success looks and feels like and the corresponding activities you’ve identified. Ask: Do the activities support one another? Do the activities conflict with one another?

Does reviewing the activities you should avoid add clarity to the kinds of activities you should pursue to achieve what success looks like?

Example: I want to run a marathon, so I need to start a training program. I want to feel energized too. As I start training, I should choose activities that aren’t boring and tedious. I hate running on treadmills. I love rollerblading and being outside. Even though running on the treadmill will help me get to my goal of running a marathon, there are other activities I can do outside that aren’t boring and tedious that will help me achieve that vision too.

Comparing Visions and Feelings

Talking through your ideas with someone else, particularly a stranger, can help you identify what you want to feel. Your close friends might find it harder to ask you probing questions like, “Why?” and “What does that mean?” because they may view the act of probing as confrontational. 

I’ve also taken teams through these questions as a way to understand the differences between how a team views success as a way to allow individual team members to connect with each other on a personal level. 

It’s important to explore what success looks like and feels like because it can help clarify what you should and shouldn’t be doing. It’s easy to add more items to the “to do” list. But it can be just as valuable to say “no”. Sometimes making a commitment not to do something means you can do something else more effectively. 

You might want to start by answering these questions for yourself. Then try it out my DIY version with your friends or colleagues and let me know how it goes. 

Note: I first posted this essay on the Reverb HR Blog:

A session I did with New Tech Northwest. Photo by Jolene Jang.