Design Your Sales Career in a Way That You Can Escape It When You Want

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⚡️ Today’s level up ⚡️

Today’s edition focuses on helping sellers zoom out in order to zoom in so you can thoughtfully design your sales career in a way that creates the life you seek.Let’s go!Read time: <9 minutesIf you missed last week, read it here.

“How should I think about the next steps in my career?”

“Write your goals in pen, but your plans in pencil.” (Greg S. Reid)

Recently, I had a 1:1 coaching session with a Strategic Account Executive at a 375+ employee late-stage tech startup.Let’s call him “Chad,” (to protect his identity). We’ve been working together for over a year, and although he’s the #1 seller on his strat account team, he’s already thinking about what’s next in his career (and life).He has exciting and daunting things on his plate:→ Turning 30 soon→ Recently married→ Wants to start a family→ Searching for their first home→ Contemplating how to jump from AE to a more fulfilling roleChad isn’t interested in managing a team, but he’s not necessarily interested in staying in an individual contributor’s (IC) role forever either.We talked about intentionally designing his career in a way to fund his life needs in a manner that doesn’t stress him out, while also freeing him up to pursue a more strategic advisory role that can scale his impact beyond being an IC.Here’s a snapshot of our discussion using a simple design framework and some prompts.

10-3-1 design framework

Zoom out a decade (10-year thinking)

A great place to begin creatively designing a compass for your career and life is zooming out a decade.Most people overestimate what they can do in a year but underestimate what they can achieve over a decade. This is known as “Gates’ Law,” and it gets a lot of people into a lot of trouble a lot of the time.I know it did for me.Early in my career, I put too much pressure on myself in the short term because I was trying to achieve so much too soon.It felt like there was an incessant urgency to do certain things by certain times:“I need to have this much money before getting married.”“I need to achieve these certain milestones before 30.”“I have to have children by 35.”“I can’t even consider retiring from a corporate role until these things are in place.”I learned (mostly by not hitting any of them when I thought I would) that early misses are not necessarily a sign of irreparable damage or a flaw in your character. It just means your time hasn’t hit yet.But it’s inevitable. And it takes work, but the kind of work that feels like a fun game you get to play.

There comes a point where all of the fears that held you back due to insecurities in your youth begin to subside. You gain a natural curiosity to explore“What if I were to start taking bigger leaps in my life?”“What do I want to know that helps satisfy this need?”“What would need to be true to make that easier in my life?”When you zoom out further, you can suspend the daily minutiae that weigh you down and start thinking creatively and open-minded about what you really want in your career and life.A helpful way to visualize this is to observe your future self in the third person (like you’re watching a movie of yourself). For Chad, we discussed a writing exercise that allowed him to craft the narrative of his future in specific detail.There were a few prompts I used to get him thinking about his future with more specificity:→ (Impact) When you think about leading or impacting others, how do you envision helping them?→ (Environment) Where do you feel most inspired to work on the challenges and rewards of purposeful work?→ (Support) Who are the people (or the type of people) that are encouraging you to chase your dreams while benefiting from your accumulation of specific knowledge and achievements?Get crystal clear by tapping into all of the senses and writing it out in full detail.Take the time to be creative and vivid. This gives you a clear North Star to keep pulling yourself towards when the trek gets challenging.

Zoom in a bit (The 3-year test)

Once you’ve clarified your future in detail, I encourage you to adopt the “3-year test.”This is about getting more focused and thinking about the next few big steps you need to take to get closer to your ideal future state. If your 10-year vision was clear and descriptive, you know you will need to put new systems in place that keep you on the path toward that bright North Star.It’s also a helpful timeframe to keep your mind focused on being the best at whatever it is you’re good at right now.Whether it’s small (like learning how to save more wisely) or just beginning to bud (like making large complex deals happen in your company) to getting serious about creating more freedom in your life (like boosting your personal brand by sharing daily on LinkedIn), going deeper into the skills that are both interesting and fruitful will be necessary for the next few years.

“Life is suffering. So figure out something worth suffering for.” (Graham Weaver)

With Chad, we clarified what’s working well right now (closing bigger deals) and what is most interesting (advising tech companies on how to use a seller’s perspective to scale companies).We used the 3-year test to build a bridge between the two.My advice to Chad, granted with my limited interaction with boards and VC firms, is that investors like to think about scale…more specifically, how to get to scale?Chad must collect a library of achievements if he desires to operate more as an advisor. Step one is creating a repeatable blueprint for closing large strategic deals. Step two is being able to get others to repeat it using the blueprint (not necessarily as a manager, but in some capacity that involves influencing others). The final step is working with multiple companies using this blueprint.Now this may feel daunting, especially over a three-year period, but the intention is to stretch yourself.Let’s collect the quotes I strategically peppered throughout this edition and use them as our prompts:→ “Write your goals in pen, but your plans in pencil.” The goal Chad has is to influence others (firm). The current plan is to use his strategic AE role to land a few more deals using a process he can document. Then, approach his employer (or another one) to work as an independent contractor vs a seller to advise his company’s strat team on how to close larger deals faster. From there, he can start to document his results and share that as an investable entity (consulting firm, VC or company advisor, coach, etc.). However, this plan is not set in stone, and he’ll likely have to adapt it as life events occur and his values change (flexible).→ “Building specific knowledge will feel like a fun game to you, but look like work to others.” What would you fill up your calendar with if you could? Can it be incorporated more on your path to accomplishing your goals? This intersection is a rich vein to tap into.→ “Life is suffering, so figure out what is worth suffering for.” Think about your life three years ago. You’ve probably been through a lot. I know you have because we all experienced the dramatic nature of Covid. Life is way different for you now than it was in 2020. It shouldn’t be unreasonable to think it could be dramatically different in 2026. But pursuing big things can get hard. It can feel heavy. What’s worth carrying on your back each day as you take one step closer to the top of the mountain?By using the 3-year test, Chad can put his current IC role into perspective. It now has new meaning connecting to his future goals, rather than the boredom and drudgery that was beginning to creep in because there was no clear direction.Knowing you’re capable of tremendous change within three years gives you laser focus to put your head down and remove any bullsh*t that stands in your way. It won’t happen overnight, but it also doesn’t have to take forever.Just think a bit longer than your company has trained you to do, but not so far out that you get lost in what’s possible.

Zoom in further (The “1 thing” rule)

Now that you are clearer on what your 10-year self desires and how your 3-year self needs to operate, you can now focus on what your right now self needs to work on (or at the very least start avoiding).A great place to start is with your calendar.Can you begin redesigning it in a way that is more purposeful?Divide your day into three parts (known as the 3-3-3 method touted by many modern productivity 2.0 creators like Ben Meer and Sahil Bloom, which was architected by author Oliver Burkeman.In essence, it works like this:→ Spend 3 hours on your most important thing.→ Complete 3 shorter tasks you've been avoiding.→ Work on 3 maintenance activities to keep life in order.I follow a similar method, but call it DFC:

I work hard to complete “my one thing” (not always successfully) as a part of my morning peak energy hours which I target to be from 8 AM - 11 AM after a “warm-up” for the day between 7 AM - 8 AM (again, not always successful).I couple DFC with PREP:

Though I am not always successful, I clearly know my ideal operating rhythm for the day. Even if I get to just 65% of my mark for the day, I know I achieve far more than most people achieve in a week. It also leaves room to explore other interests outside of work.This is not because I feel like I need to compete to win (scarcity mindset), but because I am gaining validation as I move closer to what I visualized ten years ago, but in a different way that I could’ve never imagined but have fully embraced. It “just feels right.”With Chad, we talked about the importance of setting up personal guiding principles and using them to make decisions in his life (small ones like which types of accounts to pursue) to big ones (like buying the forever home vs a starter home in a tough lending environment).Some helpful prompts:→ What’s your most important thing for tomorrow?→ When can you schedule your meetings and appointments to happen after this important deep work time?→ What do you need to check in with yourself on to ensure you’re staying on track (and sane)?Designing your calendar intentionally will not happen over time. It becomes a daily practice. But soon, you realize the true nature of life exists in the practice itself, not the destination.That’s a wrap. See you next week!In case you’re interested, I intentionally design my environment while writing these newsletters each week. Sound is a key component of the environment, and I usually listen to warm organic house beats. Here was the track fueling this edition.

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