SoC# 46: When to Make a Transition as a PM

Read time: 5 minutes

I'm Lisa - welcome to this week's edition of Stream of Consciousness - the newsletter for product leaders who want to build products and their careers more consciously, in ways that are inclusive, holistic, ethical, accessible, and sustainable.

Join 1214 conscious product leaders who want to put their time and energy into building more conscious products (and careers):

But first...a word from this edition's sponsor: PMDojo

Hi, I’m Bosky Mukherjee, Founder of PMDojo. I have over 20 years of product and hiring experience.

I help career transitioners pivot into product management or UX, gain real-world experience, get coaching and mentorship and grow their network confidently to succeed in tech. My mission is to break down barriers and make careers in product and design more equitable, diverse, inclusive, and accessible for all irrespective of experience, background, or learning abilities.

Learn more about PMDojo’s upcoming accelerator programs here. Use Code “Conscious” before Jan 30 to get a 15% discount. Spots fill up quickly!

“Look before you leap” is something that most of us can remember hearing from our parents, grandparents, teachers, coaches, mentors, and other leadership figures in our lives.

But how does one actually do this?

Especially amidst a world, technology, and economic landscape that is changing at a faster pace than ever before.

I’ve noticed many people who are either currently working in product or are aspiring product managers raising more and more questions about change.

“How do I know if product management is for me?”

“I don’t like the industry I’m in - how do I decide what to work on next?”

“I feel stuck and stagnant - how do I move forward in my career?”

Before diving into the way I approach this, I want to preface it with I’ve been through a hell of a lot of changes, both self-inflicted and that were out of my control. Change is not easy, no matter who you are, where you come from, or what you care most about in life. I’ve been a “square peg in a round hole” for my entire life so I’ve had to come up with creative solutions to complex problems because my constraints and priorities always seemed drastically different than what has commonly been accepted as the status quo.

Working in product is my third career. In 2021 I started building my own products and services as a solopreneur. A lot of what I’m focused on these days is a) figuring out what experiments I want to run and why to stay true to my values while supporting myself and b) helping others pick the right changes to make that make the most sense for them - that incorporate their desired outcomes, unique context, and constraints.

How to Know You Need a Change

I like to visualize this as guardrails or swimlanes. But these don’t matter if you don't know what matters most to you. I created a simple (free) worksheet that you can download and edit to help with this.

Some of the questions I would think about to answer this are:

• “What values are most important to me? Why?” (i.e. Integrity, creativity, family, solitude, kindness)

• “What am I spending most of my time doing? What are the impacts of this?”

• “Am I spending my time living in alignment with my values?”

• “What problems do I care most about solving? Why?”

• “How do I feel? Why?” (i.e. Overwhelmed, burnt out, full of joy, motivated)

• “Am I spending time with people I want to be spending time with? (i.e. That are inspiring me, that are helping me learn and grow, that help me live in a way that is aligned with my values?)

• “What are my desired outcomes?” (i.e. Now (immediate short-term) vs. Next (medium-term), Later (longer-term))

How to Validate the Changes You Are Making

Two books I would highly recommend reading to delve deeper into the concept of prototyping your life are “Designing Your Life” and “Designing Your Work Life” by Bill Burnett and Dave Evans. In the latter, they introduce the concept of imaging your life like a sound mixboard with 3 adjustable knobs:

1. Money (i.e. “How much money do I need to make doing ______?”)

2. Impact (i.e.”What is the impact I want to have on people, the planet, etc. with ______ that I am doing?”)

3. Expression (i.e. “How much of myself and my personality do I want to put into ________?” vs. “Am I happy following a protocol and not expressing myself at all doing ______?”)

For me, the initial mix I thought would be ideal in my next role after reading the book looked something like this:

For you, it might look different and that’s totally okay.

It might be that you’re “pressing on the gas” in each area at different times in your week, inside and outside of work, etc.

Once you’ve got a visual of what this looks like for you, think about:

1. Your Desired Outcomes

2. Your Constraints

3. Risks

4. Resulting Focus Areas

Here’s an editable template to help you organize them, like this:

For example, say you’re at a job that you hate and you want to make a change but aren’t sure what that could even look like. You also want to start your own company eventually. Your breakdown might look something like this:

You can approach this as a quarterly self-planning exercise and set milestones in your calendar to hold you accountable.

For instance, take your focus areas and break up your weeks into organized sprints that include one planning session at the beginning of the week and one de-brief session at the end of the week to keep you on track and able to quickly adapt to achieve your desired outcomes.

Set a recurring quarterly calendar event that reminds you to reassess this table and what each of these columns looks like for you as you gain more experience in different areas and learn more about yourself - what you like, what you hate, what you’re good at, what you want to spend time doing, what you don't want to spend time doing, and what you need.

The key is understanding how to break down your audacious, abstract ideas, thoughts, and feelings into tangible steps that you can easily understand and incorporate in your day-to-day life.

What has worked for you when considering making a change to help you validate that it’s the right change for you to make?

Let me know!

Soulwork 💜

• A Simple Exercise to Help Define Your Values by Dr. Rangan Chatterjee

1 Actionable Career Planning Tip 🧭

The next time you meet someone and what they do makes you feel jealous, before reacting, just pause and ask yourself, "Why?". People we meet are a mirror that can give us valuable information and feedback to help us learn more about ourselves.

• What is it about their career that makes you feel like this? i.e. Is it their schedule, the problems they are solving, that they get to travel for work, or that they lead a large team?

• Are these things you'd like to have be part of your career? Why? Why not?

• In what ways can you use this information to improve your trajectory?

Thanks for Reading!

Have a great weekend!

-Lisa ✨

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