Do you know what you really want?

Working through career and life goals with a leadership coach

Happy New Year folks! 🎉

The first newsletter of 2023 is a change of pace with a guest author.

I have a lot of career conversations with friends and strangers and one thing that stands out is that most people have no process or system to assess what they want and how they want to get there. Even when you’re aware of this, introspection can be really hard (I’ve been there). Aaron’s perspective as a leadership coach is very relevant to anyone’s career, but especially those who may be doing some soul-searching and considering part-time.


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Aaron Bieber is guest writing for us today. He's written software since the '90s, professionally since the '00s, and some of it was "actually good." After 20 years in tech, including managing at scale-ups like Wayfair and HubSpot, he is now working to transform the industry by amplifying the impact of curious, empathetic leaders.

As a tech leadership coach, I've learned something interesting: the majority of my clients, some with decades of experience in the tech industry, have no idea what they really want.

Most of my clients come to me because they have a problem; a difficult decision or some uncertainty surrounding a set of goals. Usually the solution to that problem presents itself quite easily with the appropriate application of perspective.

What happens next, though, is that my clients become aware that there is more to be discovered. Maybe they resolved the career path decision or organizational challenge that was in front of them, but they also realized that they don’t know why they’re doing all of this in the first place.

You will be happy when…

I find that people far along in their careers sometimes got there by achieving what others told them they should achieve. The promotion, the bigger role, the equity package, and so forth.

Creating Your Own Career Ladder | Retail Dietitians Business Alliance

In a podcast appearance, Marshall Goldsmith said “There is a person, the person is sad. They buy a product and they become happy! This is called a commercial. Have you seen one of those before? How many thousands of times have you been told ‘you will be happy when…’?”

One of my favorite questions to ask in my coaching sessions is “Where is your happiness in all of this?” The typical response is,  “Huh. I never considered that.” Once happiness is factored in, it changes how people engage with the challenges they are facing.

How do you find happiness? 

What does happiness look like to you, and where does your career fit into that picture? What would need to be true about the world for you to be completely content, every day? What would bring you contentment even when your job brings you stress, anxiety, or hardship?

These are the kinds of questions that aren’t answered after a few minutes of thought, or even after a few hours. Sometimes it takes weeks or months to understand how your feelings of purpose, accomplishment, and value can exist in a job that is chaotic, demanding, and stressful. It’s easy to think that you’ll be happy “as soon as you get promoted to Senior Director” or “as soon as we get this crazy project done and out the door,” but that’s a fallacy.

Michael Phelps is the most decorated Olympian of all time. Phelps has won more Olympic gold medals than any other athlete ever and has set several world records. After returning home from the 2012 Summer Olympics in London, at which he won more medals than any other athlete, Phelps contemplated suicide.

Michael Phelps Poses With All His Gold Medals

Guess what? True lasting happiness isn't connected to accomplishment or wealth or recognition or awards or gold medals. That kind of happiness is fleeting.

Just ask Ryan Holiday, author of “The Obstacle Is the Way,” “The Daily Stoic,” and over 40 other books. In an interview he said, “[T]he truth is, you can’t fix an internal problem with an external accomplishment [...] There is no amount of accomplishment that’s going to make you feel great about yourself.”


What is needed is a transformation. I help people create transformations. But this isn’t an environmental transformation; it’s not another re-org, it’s not a new job or even a new career. That might be step two, but step one is a personal transformation.

Once you recognize that most career advancement opportunities are a commercial for happiness, a sort of dopamine treadmill that ends at the same place it started, you can begin the real work.

How can you know what job is right for you if you don’t know what you’re even doing here? “What you’re even doing here” is what you might simply call your “values.” Many folks I’ve worked with strongly value personal growth, or transparency and collaboration, or taking a long-term orientation. Others value contribution to society, building community, or lifestyle balance.

Awareness leads to choice, choice leads to change

What does any of this have to do with part-time work? Awareness of what is truly important to you creates choice, and fractional or part-time work is one of those choices. Awareness takes what looks like a choice between two things and creates many more opportunities.

I’ve had clients ask whether to leave their jobs. In 100% of those cases, “stay or leave” was a false dichotomy.

In reality, there were several, if not dozens, of other options. Coaching creates awareness, which leads to opportunity, which leads to durable positive change.

A colleague of mine coached a client who shared that if money were no object, they’d leave their software job to be a full-time artist. It takes a lot of courage to say something like that out loud sometimes. It can seem like an impossible dream. From that observation, the client became aware of how much they value their creativity.

What if the choice isn’t between “full-time tech employee” and “full-time artist?” What is option three? What is option four? In what ways can creativity express itself in the job you currently have? What might be possible if “part-time engineer/marketer/sales rep” is a viable option for you? This list could go on and on.

Part-time and fractional work is just one of many exciting ways that my clients are discovering how to integrate what is truly important to them into their work and careers. The answer is never a title, or money, or a gold medal. The answer is to know enough about yourself that you can prioritize the things that matter. I love being able to go on that journey with my clients every day.

Happiness may be elusive, but it isn’t mythical. Maybe your biggest dream seems impossible today, but nobody builds their biggest dreams overnight. What is the first, smallest step along that path that you could take right now? How could more awareness open up new possibilities?

Interested in coaching? Reach out to Aaron.