How To Have A Legendary Career (Part II)
“Will I be valued as the pirate I am?”
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Dear Friend, Subscriber, and Category Pirate,
Last week we published Part I of How To Have A Legendary Career. (Read Part I first if you haven’t already.)
Let’s keep going...
5. Is the company compensating you on past performance? Or future potential?
Now, let’s say you’ve found an opportunity that is checking off these first few boxes:
✅ Company is Native Digital (or Learned Digital)
✅ Company is trying to create a new category (Be DIFFERENT!)
✅ Company is experiencing Real Growth (not Fake Growth)
✅ Company isn’t in The Brand Cult or The Product Cult (meaning they are “prosecuting the Magic Triangle”)
These are signs you’re looking at a ship worth sailing on. (They are Category Pirates 🏴☠️!)
Which means your next question should be: “Will I be valued as the pirate I am?”
There are two kinds of compensation packages you can expect to be offered as a new hire.
The first is based on your resumé, job history, and past performance.
In this case, the company is looking for a “been there, done that” person who can recreate some past success. For example, you have worked in “accounting” for 15 years. You have lots of experience in accounting. And this company needs someone smart like you, doing what you do best, which is accounting. As a result, you will be compensated in the context of what you have done in the past (accounting), which in turn will become the value of your future compensation (Accountants typically get paid $X, “So Shanice, that’s what you’ll be making here.”)
The second, which is the most common catalyst for people’s sudden rise to financial freedom, has much less to do with your past performance and much more to do with your future potential.
Instead of being compensated for what you have already done (and done well, we’re sure), you are compensated for what the company believes is the value of your future potential. For example: you’ve spent 15 years working in accounting for major corporations, but now, a startup wants you to be their first CFO—and chooses to compensate you for the amount of value they believe you can create for the company… and the category overall.
So, if the latter is how you get paid more and/or negotiate equity as part of your compensation package, the big question is, “How?”
When designing a legendary career for yourself, there are three things you need in order to change the premise of the conversation, design a new and differentiated category for yourself, and reframe the way you should be valued as an employee and team member.
1. Your Walkaway Position
How much is your financial freedom, personal agency, and “purpose” worth to you?
If it’s not worth very much, chances are, you’ll take whatever offer gets pushed across the table. But if financial freedom, personal agency, and “purpose” are worth everything to you, then you have options.
Let’s get specific.
What is the value of your free time?
What else would you be doing with your time?
Would you work on your startup that has been on the back burner?
Would you try your hand at consulting and becoming a solopreneur?
Is there another craft you’d like to apprentice in? Or would you be working on getting healthy (physically, mentally, emotionally, spiritually)?
Do you need the time to be with young children who need you? Or maybe you have aging parents you need to care for?
As we wrote about in HBR, the majority of people in their 50’s get pushed out of their industry not on their own terms. And so as scary as it might be to define a walkaway position for yourself, realize your industry has likely already decided on a “pushaway” position for you. Which is why we write often about the importance of writing the S-1 for your Personal IPO. Any “time” you spend investing in yourself, and working toward your Personal IPO, will pay huge dividends down the road. (And the longer you wait, the higher the opportunity cost.)
Having clarity around what a job is “worth” to you is how you decide what your walkaway position is—and how you gain any sort of leverage in a conversation around compensation. Because the very best leverage you can have is the conviction and confidence that Your Future, LLC is going to be legendary.
If you don’t have a Walkaway Position, you have no position.
When you stick to your position, people respect you. Which means the people who really “get” your value often come back after you walk away. And if they don’t, why would you want to work for someone who doesn’t value you the way you do, anyway?
So, what are you worth?
Or, better yet, what is your financial freedom and personal agency worth to you? Wherever that line in the sand is, it’s your responsibility to stand firm. This is what it costs to work with you. Period. End of discussion. If the company sees your value and is willing to compensate you for your future potential, they’ll gladly pay it (and you’ll gladly accept. Derek Sivers, the founder of CD Baby, calls this decision-making framework, “HELL YEAH or No.”) And if they don’t, or fail to understand how or why you believe you are “worth” that much, you have to be willing to walk away.
Otherwise, you have no leverage.
2. Your Archimedes
This is something the vast majority of people fail to understand about personal freedom and career autonomy: you don’t need the whole world’s approval.
Most of the time, all you need is one supporter, one client, one customer.
The way you find your way into companies and opportunities that value you based on your future potential is almost always through your network. However, we want to be clear here: “networking” (as in wearing a HELLO, MY NAME IS nametag and showing up to a conference center or a cocktail hour at a university) is not what we mean. Your network and “networking” are two completely different things. Us pirates have never willingly been to a single networking event in our lives—and the ones we have attended (shackled and dragged to), we didn’t enjoy.
How you build a legendary network is by playing long-term games with long-term people, and building long-term relationships as a byproduct of your working together. You earn your network by producing legendary results alongside other legendary people producing equally legendary results. The best time to start building this network of yours is as early in your career as possible. If you want your collection of friends at age 55 to be powerful VCs, brilliant entrepreneurs, and seasoned executives, then start being radically generous and thoughtfully aggressive with future rockstars when you’re 25. Keep your eyes wide open for who is going places, and find ways to work on solving problems together.
Do this for 30 years, and you will wake up with a legendary “network.”
The reason this is so important is because most forward-leaning job opportunities come as a result of people vouching for how insanely valuable it was to take a bet on your future potential back when you had no resumé or accolades to point to.
“I encourage you to bet on their future potential just like I did,” your Archimedes will say on your behalf. “She’s a rockstar high-potential engineer!” “He’s a marketing legend in the making.”
3. Your Auctioneer
Of course, you will likely have a difficult time establishing your walkaway position and finding people to bet on your future potential if your “investor base” is made up of people who don’t believe in you.
Sometimes, your auctioneer is a friend, former employer, or just someone who sees something in you.
Other times, you have to be your own auctioneer—and advocate for yourself.
The auctioneer helps frame how and why you are DIFFERENT, and also sets a minimum price that is higher than people expect—because the auctioneer is there to help you get the highest price for the value you will create.
For example: Both Pirate Christopher and Pirate Eddie have been very impactful auctioneers for Pirate Cole, who has long undervalued and undercharged for his writing talents. “You’re on the wrong side of five million bucks,” Auctioneer Pirate Christopher would say—which is a very different framing of value than, say, some of Cole’s friends who would say, “You’re charging what? No way. That’s too much.” Two different types of auctioneers, two very different perspectives on how Pirate Cole should “value” himself.
More often than not, people are not aware of the ways family members, friends, and even acquaintances subconsciously decide the ceiling of their value. We grow up believing we are only capable of what the people around us are capable of (or “say” we are capable of), and as a result, unconsciously choose auctioneers who set our “price” too low—and then get frustrated when we see others who seem to have much higher ceilings and future potential.
Instead, it is your responsibility to recognize who in your life is influencing the ways you “value” yourself—and decide whether you’re happy with your auctioneers (and the “price” they are putting on your value).
Overcoming Imposter Syndrome
Of course, everything we’re talking about here requires a good amount of self-awareness.
You have to know what you don’t know, and then you have to muster up the courage to go out into the world and find people willing to value you based on your future potential.
What keeps people from being willing to take these types of risks is what the world has named Imposter Syndrome. Imposter Syndrome is loosely defined as “doubting your abilities and feeling like a fraud.” It’s the fear you feel when your goal is to become something you’re not—and when you become aware of that fruitless goal, you crumble into a pile of hopeless ambition. The irony is that Imposter Syndrome is what you “have” when you realize you’re in over your head. You feel like an imposter because someone is paying you to do something you’ve never done.
But our perspective on Imposter Syndrome is this: you are only an “imposter” when you are a mercenary, not a missionary.
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