12 notes of (marketing) Christmas
12 notes to my younger self starting my career journey
The end of the year is always a good time to reflect back upon.
Last week, my wife was out of town for a long weekend, so that meant one thing: 3 days of daddy/daughter time with our little one. Every weekend morning, we have a ritual where we go for a nice 30-45 minute stroll through the neighborhood before the craziness of the day starts. The sun’s beginning to rise, lights are slowly turning on in the houses we pass, and there’s no traffic going by. It’s peaceful.
Aside from her sweet tooth, little one has also gotten another trait from me that she trained me on early - mornings are for quiet time, not talking. If I try talking to her while she’s in her stroller, or take a call from a family member, she gives me quite the glare that tells me what she really thinks of that decision.
So during last weekend’s strolls, I was reflecting back on this past year, but also was thinking about her + how her life is just getting started. What will she be like? What will she be drawn to doing as she gets older? What mistakes have I made that I can teach her so she doesn’t have to learn those the hard way?
And that led me down this week’s holiday-themed rabbithole: 12 notes to my younger self (and our little one) as they think about their career ahead.
Sponsor: HockeyStack
Your CEO just slacked you: "We have our board meeting in 2 days. Send me a slide with what's working + anything they need to know."
Did your palms get sweaty reading that?
Or is this an easy ask because you can easily get to this info already?
I'm neurotic about forecasting + tracking performance. I have reports upon reports and dashboards upon dashboards.
So when Emir + Claudia over at HockeyStack asked me what my perfect dashboard would look like, I immediately started geeking out.
And when they sent this dashboard mock-up back to me yesterday, I was in nerd heaven 🙌
2025 planning is here. And it's also never too late to add some solid reports or views to your dashboard, so hopefully this provides some inspiration to any of you who are looking to level up your dashboarding game.
1) Busy calendars aren’t as impressive as you think they are
I remember early in my career looking at my boss’s jam-packed calendar, then looking at my empty calendar, and thinking, “Wow, look at how many meetings they’re involved in. They’re clearly super important to our company.” And for the following few years, as I slowly started to get involved in more company meetings and have those meeting blocks in my calendar, I saw that as validation that I was “growing.”
Fast forward a handful of years and I would have back-to-back-to-back meetings and I was wearing it as a badge of pride. “Look Ma, I made it!” But I certainly didn’t feel like it. I felt perpetually behind, playing catch up on all the work I didn’t get done because I was in meetings.
Fast forward to today and here’s what I’ve learned: if my calendar is filled with more meetings than I have time to do actual work, it means I’ve become a bottleneck to my team + company. I’m either not empowering my team to make the decisions I know they’re capable of making without my approval, or we’ve hit a new growth stage that means I need to come up with new systems or resources to help handle.
2) The best leaders don’t know everything, and openly admit that
I remember thinking in my early days that to become a CMO, I would have to not only learn every facet of marketing, but be an expert in each of them as well. Demand, product, content, SEO, copywriting, etc., this person must know everything if they’re to lead an entire marketing team that handles all of those items.
Boy was I wrong.
After a few years, I quickly noticed that the best leaders, both where I worked and those that I followed, were often the quickest to say that not only do they NOT know everything, but that they purposefully seek + hire individuals smarter than they are. The leader would often have 1-2 areas of expertise, but for the other areas where they had “enough knowledge to be dangerous,” they’d have a team member leading that up who was better than they were at it and they embraced that fact, not letting it trip up their ego.
3) It’s cheaper to retain than to acquire
This isn’t just about customers. It’s about team members as well.
We put forth so much effort to acquire new customers. Then their renewal comes up. We want to raise prices by X%, but they want their price to stay as is. So they start shopping around for alternatives and potentially churn. Want to know how much ARR is lost by not meeting them halfway? A significant amount, and all because we wanted to raise their price just a little bit (which, by the way is often at least 10x less than what we’re willing to pay in customer acquisition costs).
Same goes with team members. We spend a massive amount of time sourcing candidates or sorting through applications + conduct countless interviews to make that next great hire. Then their work anniversary comes up. Inflation continues to rise. They’ve been meeting or exceeding their expectations in the role. But we are only willing to offer them a 2% raise. Same scenario as the above - the cost to hire and ramp a new employee to be paid that same amount, or maybe slightly less - is it really worth it? No, far from it.
4) The buyer’s journey is not sequential
For the longest time, I've always thought of the buyer's journey and retargeting as a funnel a prospect needs to go down before becoming a customer. You know, the funnel that goes like:
Step 1: "awareness" ad
Step 2: "pain point" ad
Step 3: "benefits" ad
Step 4: "use case" ad
Step 5: "CTA" ad to get a demo/sign up
The problem is that it's typically constrained to 1-2 channels/platforms and requires the prospect to successfully consume the content at each stage to progress to the next. And the numbers do not play in your favor. If you start with an audience of 100,000 individuals and makes it to the next step at an average CTR of 0.4%, the numbers go as follows:
Step 1: 1,000,000 people see ads, 0.4% click
Step 2: 4,000 people see this ad (wow, that dropped FAST)
Step 3: 16 people see this ad (WTF just happened!?)
Step 4: there is no step 4 - no one makes it here
I’ve said it before + I’ll say it again: this is why ecosystems > funnels.
5) Seek ikigai over a pay jump or impressive title
It’s easy to be drawn to an opportunity that pays you a little more, or gives you a slightly better title. But career fulfillment doesn’t just come from one of those items, it comes from the intersection of 3: pay, people, and purpose.
I don't have hard data on this, but anecdotally what I've seen is:
👉 Some people sit outside of all 3 circles (let that really sink in for a second)
👉 Most people only sit in 1 of the 3 circles
👉 A minority of people sit in the overlap between 2 of the 3 circles
👉 A truly small percentage of people sit perfectly in the middle of all 3 circles
Having worked in various places throughout my career, I've experienced all of these scenarios.
When I was outside of all the circles, I dreaded going to work, would count down the minutes until I could clock out, and did everything I could to not have to think about the fact I'd have to go back to do that same thing the next day.
When I only covered one circle, the job was simply something I did from 9-5 and I would be on the lookout for the next, better, thing.
When I covered two circles, going to work was 10x more enjoyable. Most consider themselves lucky to be working at a place like this.
But as I now cover three circles, work has become fun. I genuinely look forward to each day and recognize how incredibly rare this is. Find your three circles place.
6) Big logos are impressive, but your biggest advocates are often the smaller logos
We all want the big logos on our website. The well-known brands that we can proudly showcase as customers. The companies that we think will get our prospects to think, “Wow, I can’t believe BIGCORP is a customer of theirs! They must have an amazing product if they’re a customer.”
But here’s the reality: those massive logos come at a cost. Additional requirements. More resources needed to support them. An endless stream of “feature requests.” Then when a customer reference is needed to land a big deal, they’re mysteriously unresponsive.
On the flipside you have your smaller or “normal” customers. The organizations that, while may not be a household name, are running a great company and are a pleasure to work with. Even more, they’re often the ones who are our biggest advocates in the market, proactively sharing their experience and recommending our product to their peers without expecting anything in return.
Keep all of this in mind, especially when the inevitable allure of “going upmarket” appears.
7) Greatness comes at a cost
Over our careers, new entrepreneurs, marketers, leaders, innovators, athletes, and others appear that we aspire to be like. "If I could just be them for a day, must be nice…”
And for a long time, I thought that as well. What I would have given to have been like Marcelo when I played outside back in college. What I would have given to have the entrepreneurial drive of John D. Rockefeller. (Political views aside) What I would have given to have Elon Musk’s brain.
Then one day (and I genuinely wish I remember where I heard this first) I heard someone say before you envy someone’s position or achievements, think about if you’d want their entire lives. You don’t get to pick what skills or attributes of theirs you’d like. You would have to be willing to swap 100% of your life for theirs.
That’s when you realize that while there are certain achievements that many of the individuals we aspire towards that we’d love to obtain, we realize that they typically come at a cost. They have poor health. They have been divorced multiple times. They don’t have good relationships with family members. The list goes on and on.
8) You get the salary after you do the work, not before
Want to know the easiest way to get a raise? Start doing the work before you’re paid to do it. Show you can do it. Show that you’re an irreplaceable team member who continues to level up and help the company. Make it a no-brainer for leadership to want to give you a raise or promotion.
Just because you have a degree in a certain field or a certain number of years experience does not mean you’re entitled to a certain salary. Salaries are earned, not given.
9) Adaptation > planning
“Sam, it’s annual planning season, what are you talking about??”
Yeah I know, and I also just wrote a two-part series about annual planning (part 1 and part 2), so this sounds a bit hypocritical, no? Planning is incredibly important, don’t get me wrong. You won’t find a year or quarter that goes by that I don’t have a plan for. But I recognize that even the best plans have wrenches thrown in them, and it’s the ability to adapt to those variables that dictate long-term success.
Who planned for the rise of AI + ChatGPT last year? Probably very few, but here we are, with legacy companies sticking to the plans “they’ve always used” and new leaders emerging who are embracing these new technologies.
Who planned for COVID back in 2020? Thinking not a single company. And in that time you saw companies and industries get entirely shaken up by a “new normal”, their ability to navigate through it relying on adapting to the new circumstances vs. sticking to their initial plan.
10) Know what to prioritize
How many of you have a list of big ideas/experiments you want to explore, but never get to because "more urgent” things come in? There's a popular concept that engineer + developer teams have where they have a hack week to dive into areas they're curious about, but often don't have the time to get to in their normal workdays.
Our marketing team uses a shared Asana board and we have a section titled "Ideas/Brain Dump". I noticed last year that it was getting more and more great ideas and experiments added to it...but it was getting longer and longer because the team didn't have the time to properly sink their teeth into any of the items.
Too often we let the interesting + important things slide because we “don’t have the time” (aka, we're too busy addressing the "urgent" things). But if you zoom out and look at them from a long-term perspective, you'll find they're actually much more impactful than those "urgent/not important" items we keep pushing to the top of our to-do lists.
Remember, urgent ≠ important. The "Urgent/Not Important" box has gotten away with taking up too many resources for too long.
At the end of the day, the "Not-Urgent/Important" box is where employee, team, and company growth happens.
11) You’re in charge of your future, not your manager
I remember a good 12 months of being strung along about a raise that was “going to come next quarter, I promise!” And I trusted my manager when they told me this. While they were promising and promising me this raise that was sitting with Finance but “things were tight,” an eye-opening moment happened - they got a promotion.
I’d put all my faith in them to take care of me, only to realize that they were putting themselves first. Now the takeaway here isn’t to become a dog-eat-dog type of person, but there were two things I did learn and have applied since then:
If you want something, you have to make it happen. Want a raise? Want a promotion? Want that new trinket? Become tenacious in doing everything you can to make it happen. Take on more responsibility. Develop a relationship with your manager’s manager. Start a side hustle. Don’t let your future rest in the hands of someone else.
If you get to the position where you dictate this for your team, remember how you felt in that moment before. If team retention and trust are important to you, do the exact opposite thing. Have transparent conversations about what’s important to them, what they’re enjoying, what stresses them, what they’re planning for with their career + personal life. Then meet them halfway in saying how we can accomplish those together. They want a raise? Give them additional responsibilities or projects to help with.
12) Say less
Early in my career I noticed something interesting as I’d sit in on large departmental meetings.
95% of the meeting was filled with talking from individuals who didn’t seem to have any real point to make, but felt the need to speak frequently so their voice was heard.
And then there was 5% of the meeting where, when 1 or 2 specific people spoke, everyone shut up and hyperfocused on what they had to say.
I learned three lessons when that realization finally hit me:
Don’t be one of the 95% that speaks just to speak
When you speak less, more listen
This concept applies equally to your content strategy
See you next Saturday,
Sam