What Does Good Advice Look Like?

By: Jen Shoop

Have you ever received bad advice? How did you handle it? Do you now have a litmus for separating the trustworthy from the circumspect?

For some reason, I found myself fixated on this after watching the most recent installment of HBO’s “Succession.” Without spoiling anything, there is a scene in which Kendall Roy is riding an underling to inflate speculative numbers on a program’s potential, and the employee visibly squirms in his seat before acquiescing. Of course, there is a power dynamic afoot, and Kendall is less an adviser than a tyrant, but I found myself reflecting back on moments in my career in which individuals more studied, more senior than I passed along advice that did not feel right to me. Over time, I learned that refuting or even mildly questioning the input rarely yielded anything besides a “you don’t know what you’re talking about” response, and so my routine was to nod speculatively, as though turning the input over with solemnity, and then communicate that I would reflect on how I might put the suggestion into practice before swiftly ending the meeting or changing the topic. This would buy me time to digest and, usually, discard the advice, fashioning a well-thought-out rebuttal if required.

On occasion, I have found that advice is lightly-veiled self-justification. As in: “Well, I did this, and everything turned out OK for me!” or “I’m not sure how well things turned out, but I’m going to try to explain all the reasons why no other paths could have worked to account for my actions,” or “Here is a chance to convince myself, through the puppet of this other person, that I did the right thing.” None of these subtexts are malicious. To be honest, their impetus moves me: most of us want to do right by ourselves, right by the world. But any one person’s advice is necessarily narrow, idiosyncratic, shaped by unique circumstances that likely do not mirror my own. If I can find patterns across advisers, great. But I must not let data be the plural of anecdote. I was reminded of this recently while talking to different experts about a technical aspect of running this blog. There were lots of confident opinions — but they scattered across a map. My go-to response is: “Hm, let me think about that.” I like to hear a lot of different opinions — in the entrepreneurial world, we called this “mentor whiplash” — and then sift through them and see which resonates best, or if obvious patterns emerge.

Someone once told me that “good advice always feels annoying,” and the sentiment landed. There is often a rudder pointing me in a direction though the path looks perilous or fatiguing, and I can glimpse other, easier, more appealing ways out. But I have found that there are few shortcuts when you are doing something that is really worth doing.

I also think that sound advice tends to fall in line with the “good teachers tell you where to look, not what to see” adage. Which is to say: I am chary of hyper-specific counsel. How can anyone fully understand the complexity of your own experience? If a mentor is giving you marching orders rather than a rallying cry, it might be time to pause. (What’s really happening here?)

As I re-read these rivulets of thought, I am struck by how shape-shifting, how frustratingly imprecise they are, and I find myself thinking of a quote I recently came across by Marc Randolph, co-founder and first CEO of Netflix:

“Unfortunately, our educational system rewards a behavior that doesn’t really exist in the entrepreneurial world. Which is getting the right answer. For an entrepreneur, the objective is to provide a wrong answer as many times as possible.”

He later added:

“Gain the ability to make decisions based on incomplete, inconclusive, and often contradictory information.”

I am drawn in by the thread between the two: there are often many paths forward, and the goal of selecting “the right one, right away” may ultimately be a fool’s errand. Sometimes we must fail many times before we find the right way, or we must choose the least bad option, knowing full well about the risks.

These are not cheerful directions, but I think they are honest, and they do not seek to gain anything by their propagation. By this I mean that Randolph is not suggesting he has always done the right or best thing, but that he has learned to make decisions swiftly in the face of complex inputs, and perhaps this is the facility we must prize.

What do you think?


+I really do like this advice though: “Make what you’re doing the most important thing.”

+Nothing changes if nothing changes.

+The whole sky is yours.

Shopping Break.

+This shibori-print dress is gorgeous, and under $120. Don’t miss the back!

+This is next on my list for Vitamin C products to try (Biossance’s formula is my current favorite). Have heard SUCH good things. Actually been hearing a lot of buzz about the entire Goop skincare line. Also dying to try this exfoliator, which multiple beauty bloggers have raved about.

+This floaty Tuckernuck dress looks like something by Doen.

+A great, under-$100 white blouse to tuck into jeans when you don’t know what to wear. While you’re there, check out this beautiful sun dress.

+I know people love those Stanley water bottles but this Owala one is more my speed. Love that you could throw it in a bag and not worry about leaks.

+Love these cropped trousers. Wow.

+Significant Other has some really gorgeous dresses that get the Agua Bendita vibe for about half the price — but don’t feel like imitations. I’m obsessing over this one and this one in particular.

+There is almost nothing Westman Atelier releases that I don’t immediately add to my cart…I don’t need their new “skin activator,” right?! I’m desperate to try! I still absolutely adore and swear by their Vital Skin Foundation Stick. I don’t use it every day, but when I want a bit more coverage, it’s primo.

+Adorable tasseled ottoman. Found through Grace!

+This $59 sunshine yellow top is so fun with high-waisted white denim. Reminds me of Farm Rio!

+This Etsy shop makes the most beautiful birdhouses!

+Pretty gingham suit.

+This little H&M frayed basket bag is cute.

+For my golf and pickleball girlies.

+A nearly fully-stocked run of Adidas Gazelles. These shoes (and the Sambas) are so hard to find these days!

+Into these linen striped shorts.

+Fun tunic dress.

+The most darling little bubble for a tiny girl.

+Fun destination sandals.

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4 thoughts on “What Does Good Advice Look Like?

  1. Hi Jen, I have a request for your next ask magpie – bachelorette in Austin (I’m not the bride), final night will be staying in and dress code is “cute pajamas.” If you can get to it, thank you!

  2. I agree, Jen – Randolph’s advice is certainly more real-world than anything we learn in school! I will add something my dad frequently tells me to the decidedly not cheerful adages you’ve shared: time is money. Unfortunately, in a lot of professional and personal contexts, we sometimes have to make decisions quickly and choose to execute them with confidence and flexibility because the cost of waiting to find the perfect solution is too high. Better yet, there often is no perfect solution.

    1. A lot of wisdom here, too — “there is often no perfect solution”! On the “time is money” front, Mr. Magpie and I often do this calculus when trying to figure out whether to outsource something or handle it ourselves, whether this pertains to the lawn, to cooking, to grocery delivery/shopping, etc. Sometimes the math is imprecise but still clarifying.


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