I don’t know how many people I’ve helped navigate work and career choices - but it’s been many over 20 years, starting when I was first leading teams in restaurants around the world. These conversations and decisions have covered every level from hourly employee to emerging leaders to founder and CEO and been in corporate and entrepreneurial environments and as a leader, peer, friend, or advisor. I’ve also benefited from incredibly helpful counsel for my own decisions over the years.
I learned that it’s not so much specific advice that people are seeking when navigating career decisions, as everyone’s situation is so unique. What seems to be most helpful is a starting framework that each person, leader, or team can make their own.
This is even more true now that options for work, jobs, starting a business, making money, etc. continue to expand and change - although not equally for everyone. The “Great Reshuffling”, the “Great Resignation”, the gig and creator economy, web3, NFTs, DAOs, the broader shift to remote work, and the tools to more easily build businesses and connect talent are driving many to consider career and work changes at an unprecedented volume.
And while it’s the wild west of opportunity for some, there are real challenges to these decisions for many, including paying the bills in the short term, responsibilities for others, a desired growth path, and the immediate opportunities one does or does not have.
Regardless of how the options may change, the effectiveness of this framework and exercise seems to endure. I hope you leverage this approach for yourself and to talk through career or work moves with your team, your leader, your friends - anyone who is looking for some structure in their thinking. It is more effective with voiceover, coaching, and facilitation, but this should be enough detail to get you started.
This is a thought exercise to check-in on what matters and help you architect what is best for you related to career or work choices and to help you be more respsonsive to exciting opportuninties that come your way.
First, go through it proactively - not thinking of any specific opportunity other than where you are now and your near-term goals and desires. Just establish a baseline. Later, use it to help think through specific opportunities or options for the next steps in your work and career.
Follow the 3 As woven through most of my posts: Ask, Answer, Act.
Ask - the questions of yourself and learn benchmarks that can help you see things more clearly. Go through each column on its own. Do not let one column’s details affect your thinking for the other. Give each topic the focus and clear thinking it deserves. You’ll blend it later.
Answer - once a year or as big life events or opportunities affect what is in these sections.
Act - use your more organized thinking to make more confident changes, asks, leaps, investments in yourself, and decisions. And remember, if you are in a role to do so, help others do the same.
Step 1: Values // The Foundation
First, ground yourself in your values. They may not change much, but they can change - or the way you see them coming to life may be different as time goes on. This is your filter, and if key values can’t be met for an extended period, big issues typically show up.
Not everyone has the choice to “live their values fully all at once”. For example, if what you value most is time with family and friends (A), and the only or best job to meet most of your needs to provide for your family (B) conflicts with that value (A), you may have to choose value A to deliver on value B. Of course, what you want is for the prioritization of (B) to lead to more (A) or to help meet other values on the list. The evolution of work, talent, and learning are changing this for many, but we must remember it isn’t changing it equally for all.
To reflect on your values, ask:
What matters most to me now? (If you don’t know where to start, Google ‘Core Values Lists’)
Chose your top few values, and rank them. 1 is too few, 10 is too many.
As you think about different opportunities with various combinations of attributes at the end of the exercise, ask, “To what degree is this value able to be met?”
Revisit this each year or with major life events
…and if you want to go deeper:
20 years ago, when I was a Training Manager at Hooters and barely 23, I started using a ‘Values Workshop” in management classes that I taught. We presented common values (edited as needed for the region, culture, or country), and asked people to identify their top 4-6. They we played an “Invest in Your Values” game, where people had to invest pretend $ in descending order in their top value, until they ran out of $.
So the number one value had the highest denomination, next had next lowest, and so on. It is always wild watching how serious people become - changing stickers, toiling over which makes it to the top. It reminded me of how seldom we think about our values consciously. We had a few people share their top value - and it was great in a group for people to remember that top values differ, and that affects what drives people.
Then we asked, “using only these values that you have selected and invested in, to what degree is it possible for them to be met right now?”.
We used green, yellow, and red stickers. Green for high likelihood of that value being met, yellow for some likelihood, and red for not able to be met. I have had people quit in the week following the workshop from the red stickers. But more often I’ve had productive conversations about what is possible that may not have been appreciated or understood. Sometimes what hey thought was yellow was green, or what was red could be turned to yellow or green with different decisions and approaches. It broke my heart to think that values that could be met weren’t realized, and when we were at an impasse, we made changes.
Some version of this values exercise has been foundational to guiding myself and others at all levels through big decisions. Do this for yourself, and if you lead a team, it’s a worthwhile exercise to do with them. Just be sure people are not left alone to stare that their exercise and make unhelpful assumptions. It’s best when talked through, especially with younger employees or people navigating more complex dynamics.
Step 2: Answer the questions in each of the three columns/sections independently - only focus on that topic.
Column 1: Financial
Evaluate where you are and what you want and need. 1-3 years max. It’s great if you have a financial plan and a long-term wealth plan (I recommend it!). But many don’t, so practically, if most can think strategically about goals for the next few years and use that as a filter for the next immediate step, it’s still very helpful.
Where you are (income, expenses, liquidity, assets broadly) and what are your needs - can they be met? If so, what’s your wiggle room or cushion? If not, what do you need to meet those needs?
Goals (next 1-3 years) - where do you want to see it go, move, change?
Other benefits with $ value
Equity/ownership/assets/longer-term wealth creation
LTIP (Long Term Incentive Plan in equity or cash)
Passive income / alternative income streams
Other long-term financial goals that this may ladder up to (if you have them)
Column 2: Ego/Optics/Affiliations/Scope
What matters to you that makes you feel proud about a role, a company, a body of work now and over the next few years? Consider the elements that are often tied to external views of what you do: mission, title, size, reputation, etc. Be honest. If you have goals to join a well-known tech company, start your own business, be a VP in two years or run your own division in 3 years, this is the place for those goals.
Pressure test it by thinking about different companies, scopes of responsibility, and titles - if they offered you a role, how would you react? What would it take to get you there? Do these things pave a path to the best outcomes? Some more than others? These things matter more to some than to others and affect decisions (sometimes misguidedly so).
In addition, these things have different weights in various companies or endeavors, but you first need to know what matters to you to calibrate it to what you are considering.
Type/Industry/Positioning of Brand or Company
Startup, Growth Stage, Scaled, Mature?
Good for the planet or not?
Good for society? Neutral? Negative?
Known brand or stealthy co.
Reputation and culture
Size of company or business endeavor
Size, culture, and work style of the team (or people you would work with)
Title (Remember, you are focusing on this column alone - don’t mix these other things with money. Yes, they are often correlated, but not always). Ask, “what is important to me, and why?” (ie: signaling growth over time, indicating the scope of responsibility, my intrinsic motivation, reputation, etc.). We’ll question assumptions later, but get it all out in this column.
Type of responsibility (P&L, leading teams, reporting to the board, lead your own market, etc.)
Perceived risk vs stability (this is the emotional side vs. the financial element in the money column)
Role on the team/who you report to
Ability to make an impact (this is also what’s great for the company!)
Column 3: Capabilities A & B
A) What skills do you have (objectively evaluated) that should be put to work for you to add great value? These are the skills that you have mastered that others can see and appreciate in almost any situation. They are your most developed capabilities. B) In what areas would you like exposure or experience to continue to grow?
Capabilities A) What you have now (list 3-5). To what degree can you objectively shine /use the skills you have? (what are your assumptions here?)
Capabilities B) Ability to learn and grow – to what degree can you objectively learn and get experience in new areas (what are your assumptions here?)
The ideal mix of these two varies by person and by the season they are in, but most need some mix of both to thrive
Step 3: Consider these three sections independently. Review your answers in these columns and lists. Sit with it. Where did these beliefs come from? Are they dated? Are they serving you? When you put a few years together of acting on these beliefs, how does it play out (best guess)? Do you need more information on what’s possible? Or…are they exactly what is important to you now for all the right reasons with relevant intel?
Step 4: Think about what attribute may be traded for another (by your own design or just how things sit). As you start to connect things you have and want across the sections - be careful not to assume something in one column fully drives something in another column.
I often have deep conversations around title, learning, capability, scope of responsibility, and complexity of orgs with people who were overestimating or underestimating one element’s impact on another. Or they took themselves out of the game for an opportunity because of flawed assumptions, past experiences, rumors, lack of representation in like roles, or not getting the full story or credible info.
Examples of common flawed correllations: I can’t learn a new skill if I’m in the same department. If I get a bigger title, it’s more $ or conversely, the $ come always with the bigger titles. Title in a small org is same as title in big/complex org. What many don’t think about - if you take on new/more, you are more in the Capability B section and often lighter on Capability A - at least for a while.
Some aren’t ready for what it means to be compared to a new benchmark at that new level, and some absolutely are. Some get bigger with leaps in responsibility, others need more of a steady ramp to be effective, and some thrive with being linear and deep vs larger and broad.
The point is to think it through and have the strongest foundational beliefs that move away from assumptions to see both the wide world of possibilities and the grounded facts you should know. Talk to people, get diverse counsel and perspective from those who will speak candidly.
Step 5: As you think about future opportunities or possibly one (or many) in front of you now: mix the scenarios and level the attributes and your goals are met or fulfilled. Consider various hybrid opportunities:
High on financial, mid on ego, mid on capabilities (A, B, or both)
Mid on financial, high on ego, high on capabilities A, but not B
High on a good number in all 3 columns: your work or business utopia
Keep mixing the scenarios to get a sense of what you’d be willing to do vs what your Utopia is
Remember - values are the first filter when at all possible
The simple act of considering these scenarios, talking them out, and processing them helps you make better decisions for your path. As a leader in a company, I want to match up as many of these as possible between roles and people, because it’s good for everyone, although perfect matches aren’t always possible.
Ultimately, I have the bias of broadening experience, optimizing for learning and impact, following your gut, being sure you are paid what you are worth, and building assets and passive income streams, all while working with great people. But that would have been a very short post (ha) and is not enough of a framework for many to work through their ideas and options.
Keep working toward your evolving ideal situations and make big bets on yourself when you can.
Be sure to diversify your purpose portfolio, so you get your sense of self from a healthy variety of sources and work doesn’t “define you”.
Feel confident in making choices that are not perfect. The greatest things to come are often unpredictable!
The goal is to keep moving in a direction that helps you grow and sets you up to make the greatest impact through what you chose to do, what you chose to build, and the organizations you work with.
If you are a leader, have these conversations with your team members proactively and if they have questions about pieces of their career - it’s incredibly powerful.
I hope this tool helps you move more confidently through opportunities you create for yourself or receive!
P.S. For those new to Checking In, welcome! I share a few highly actionable posts each quarter for all getting the emails, and if you would like more intimate connection and deeper dives on these topics beyond these posts and additional resources, I hold monthly community zooms for the paying subscriber community. It’s how I love adding value beyond the newsletter itself.
Love the framework! Thanks for sharing more on your journey.
PS - I've considered purchasing AG1 several times, but I don't like the huge upfront $ commitment for something I may not like. If AG offered a trial size of 5 or 10 travel packs, I would buy. Several friends have said the same thing.
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