While you may not know me personally, you probably know quite a lot. The thing with the internet is that often, you only see the slice of someone that the algorithm deems interesting, or useful.

Rest assured, I have many slices. I have the one that writes here - self-assured, future-seeking, fueled by a desire to create positive impact and hope.

I have the one that works on a team - collaborative, creative, enthusiastically audacious.

I have the one that plays host - high energy, inspiring, thoughtful and detail-obsessed.

And then, I have the one that comes when I’m alone - fearful, wandering, unsteady.

In the 10 years that have followed my diagnosis and treatment, I’ve tried tirelessly to find purpose and joy. I’ve found both in friends, family, love, and work, with work being one of the most interesting and dynamic vessels. Hence, my obsession with good work.

Now, imagine you and I in a warm, bustling coffee shop. Every person around us on their way to somewhere else - some on their phones reading or smiling at a text from a new love, some chatting about niceties or the weather, some staring into the distance, taking a mental moment for themselves. Humor me and close your eyes and really picture it for a moment.

Great. Now, if we were grabbing coffee today, here’s what I’d tell you if you asked me what I’d learned in these 10 years:

ps: if you read these on linkedin or in notes, this is a longer version with some suggestions of how to implement!

1// Never keep a kind thought to yourself

Being nice to others, out loud, is one of the truest forms of self care and generosity. Do you remember a time when a compliment or word of encouragement stuck with you? The person who gave it probably didn’t give it a second thought, but it turned your day or week around or even better, gave you the confidence to do something you might not have done otherwise. You can be that person for others - for free! When you think something nice, say it out loud.

Practice: give one (genuine) compliment a day for the next 7 days

2// As the poet Charlie XCX says, fall in love again and again.

Experiencing love and loss and love again is pure magic. Fall in love with your neighborhood, your pet, your partner, your goals, your routines, your imagination, your book, your community. When you lose love, know that there are a thousand opportunities to find it again if you choose to. The point of life is to live, and nothing makes you feel more alive than love and loss.

Practice: Write down all the things you love and why. Romanticize even the smallest things in this list.

3// Be your best friend, not your worst enemy.

Every minute of every day, you create an impossible-to-ignore feedback loop for yourself. The way you talk to yourself holds a huge amount of power because it feels like truth. It’s easier said than done, but resilient and positive self-talk is a skill that you can master if you commit to it and practice.

Practice: Pay attention to what those who love you say - how does that compare to what you say to yourself?

4// Have some fun, damn it.

There are hundreds of reasons to prioritize having fun - social, emotional, mental, economic. Add some color to your home, add a meme to an email, name your AI agent your favorite cartoon character. Try a new activity, go on an adventure, indulge your inner child. Have a dance party in the middle of the day, get the random nail art, revel in a good belly laugh. Put your phone away. Bring people along for the ride, and share your joy.

Practice: Make one work task more fun this week. Optional but encouraged, have a dance party right this second.

5// Stop sanding down your edges to fit in.

The internet has given us extensive choice of the communities and people we spend time with. You do have to put in the work - first to learn who you are, then to find others like you - but once you do, you’ll find there’s no need to reduce yourself to a smaller version in order to fit in. Certain environments require a specific version of ourselves (work tends to be guiltiest of this), but instead of sanding and abandoning those parts, we can find other spaces to allow them to shine.

Practice: Run a search for communities related to something you’re particularly interested in. It might be birding or product, musicals or AI, Pokemon or data analysis. Consider joining and actually participating.

6// Everyone’s afraid of something.

I’m afraid of getting sick again, I’m afraid of missing opportunities, I’m afraid of taking the wrong bets on myself or others, I’m afraid of upsetting or offending people, I’m afraid of letting people down. Those fears, unfortunately, are never going to go away. Instead of ignoring them, I use them to motivate me to create community, care for others, and get really good at what I do.

Practice: What’s one fear that you pretend you don’t have? Say hello to it and imagine shaking its hand in an agreement of coexistence.

7// Pay attention to what you feel jealous of, and go get a version of it for yourself.

Jealousy is strange in that we’re taught that it’s something we should never feel. I feel it often - so many people have so many amazing things, opportunities, and qualities that I wish I had. Instead of feeling guilt about those thoughts, I love the phrase ‘love it for you, want it for me’ - there’s plenty of happiness, success, growth, and opportunity to go around. If we pay attention to where our internal compass is pulling us instead of ignoring it, we can reach those goals more quickly.

Practice: What’s one thing you’ve felt jealous of recently and why? What’s one thing you could do this week to work toward having your own version of that thing?

8// If you want a village become a villager.

Being a villager can be challenging. Sometimes you’ll organize something and everyone will cancel on you. Sometimes no one will thank you for the nice thing you did. You have to keep going. The compounding effect of showing up for others is that they will, eventually, show up for you. Plan things. Say people’s names in rooms they aren’t in. Do favors without expectation of anything in return. Anticipate people’s needs and acknowledge their fears. Do the work so when you’re on the brink and need help, help will be there.

Practice: What’s one gathering you could organize in the next 45 days? Do the practice exercise in this issue.

9// Never stop learning.

While this may feel very of the moment, it’s always been true. The more information, context, experiences and opinions you can take in, the more nuanced, informed, and ‘you’ your perspectives will become. Get comfortable being bad at things in public, because you have to start bad to get good. Update your opinions and perspectives with each new piece of information - it's cool to change your mind.

Practice: What’s one thing you’re learning or want to learn right now, and can you share that journey (not the destination) with others somehow?

10// Understand that the only limit is physics.

Start listening to what pulls you, and chase that sh*t down.

Practice: If it helps, reply to this email and tell me your wildest dream. I’ll keep it safe for you, but only if you promise to give yourself permission to pursue it.

Thanks for welcoming me into your inbox and giving me space to work through all my slices ✨

Cheers to a few more decades.

Each week you’ll get an idea to consider and an exercise to put it into practice, plus my POV on a reader question about work. The goal will always be to push you toward more good work, because I think you’re capable of it.

If you’re new here, you might also enjoy my previous essays rage against the machine, everything is sales, or find your fun.

Today’s idea

If everything fell apart, what would you have to lean on? Which levers could you pull? Who could you call? Would they pick up?

You’re probably not thinking enough about proactive self-preservation, and you should be.

The path ahead of you very well may be easy and fruitful. Equally likely though, is that it will be challenging and full of potholes and unexpected twists and turns. Such is life.

Blame AI, blame the patriarchy, blame your astrological chart, but know that no one is coming to save you unless you give them a good reason to.

Please note the ‘unless you give them a good reason to’ part - people will come save you if you prepare, invest, and save them in return. You have to start before you need something, though, and you have to mean it.

Self-preservation really just means expanding your surface area, and doing it from a place of give vs. take. It means carving your impact beyond your job title toward a sustainable, underlying reality that people will want to work with you no matter what happens. It means actively investing into relationships with people (loose and strong ties alike), continuously building your toolkit, and ensuring you are more than your job to both yourself and others.

1// Investing into your relationships

I know I’m a community nut (google me), but I really do believe with all ten toes that building and participating in community is now more important than it’s ever been.

Community can mean so many things - a bookclub with your neighbors, a regular pickup basketball game, volunteering for a local cause, gathering others who are into the same things you are, virtual hobbyist chat rooms, etc etc.

Fostering community is hard, delightful, and pays off in dividends. It’s unequivocally fun to find others who care about the same things you do and like to nerd out with you on those things. It’s also comforting to know you have a group of people in your corner when shit hits the fan beyond your immediate friends and family, who often can’t be much help beyond emotional support.

Really dig deep and think about what type of community feels most natural for you to build, and start. Be the one who offers to find a time and day that works. Buy the zoom license so the group can spend a whole hour together. Open your home to your neighbors. Ask follow up questions, and actually listen to the answers.

2// Building your toolkit

You’ve heard this a million times in the last 6 months - you have to keep learning. I’m not here to tell you to learn AI, but I am here to tell you to keep expanding in whatever direction you spike in. As the world continues to morph and change around us, the best thing we can do is find the bits of it that pique our interest and dive in head first.

Learn new skills, pursue a new passion, build a side project, ask more questions, shadow a coworker. Entertain the idea that there is more to you and your capabilities that you haven’t yet discovered. Don’t be afraid to invest or explore outside your current role or path - you never know what or who you’ll discover.

3// Be more than your job

Your identity simply cannot be based on someone else’s perception of you and your work, or their decision to keep you (or not) during a layoff. As much as your job being your identity isn’t sustainable for your own self-worth, it also creates a public understanding of you that is far too vulnerable.

You must learn to own and craft your own identity - otherwise it will be created on your behalf. Learn to tell your story. Invest time and energy into mastering talking about yourself in a way that is compelling and differentiating.

Can you name your skills and spikes without hesitation? Can you confidently and concisely tell someone what you’re passionate about and excellent at? If not, get to work.

In practice

Here’s one exercise for each bucket:

1// Investing into your relationships

Your task: Gather more than 2 people together that aren’t your close friends or family - do it in the next 45 days.

I’ll even give you a shortcut by getting an LLM to help you plan it. Drop this prompt I wrote into any LLM, answer the questions in section 1, and hit enter for a step by step plan.

You are a thoughtful gathering design advisor helping me plan a gathering in the next 45 days. Your job is to ask me a series of questions, then use my answers to make one specific, actionable recommendation for a gathering I should host.

Step 1 — Use my answers to these questions

Read my answers to the below questions:

1. Who is your natural community right now? (colleagues, neighbors, old friends, online followers, a mix?) [ANSWER]

2. Tell me about the work you do.

3. What’s something you’ve been wanting to talk about, learn, or explore lately — personally or professionally? [ANSWER]

4. How comfortable are you with hosting? (first-timer, occasional host, or seasoned?) [ANSWER]

5. Do you prefer in-person, virtual, or are you open to either? [ANSWER]

6. If you prefer in person, how many people can you realistically bring together? (intimate 3–5, small group 6–15, larger 16+?) [ANSWER]

7. What’s your energy level and bandwidth over the next 45 days — low, medium, or high? [ANSWER]

8. What are you hoping to get out of this gathering for yourself? (connection, visibility, learning, accountability, fun?) [ANSWER]

If any answer is vague or minimal, ask one focused follow-up question to clarify before moving to your recommendation. Do not proceed until you have enough to make a confident, specific suggestion.

Step 2 — Make One Recommendation

Give a single, clear recommendation — not a menu of options. Every recommendation must be low-cost or free to host. Include:

• Type of gathering — dinner party, workshop, book club, panel, walk, online call, etc.

• Specific topic or theme — tailored to what I shared

• Format and structure — how long, what happens, how it flows

• Guest count and who to invite

• A compelling name or working title for the gathering

• One concrete first action I can take in the next 48 hours to make it real

Guidelines

Keep your tone warm, encouraging, and direct. The goal is for me to finish this conversation feeling excited and ready to actually host something within 45 days.

2// Build your toolkit

Your task: Watch a couple free Lightning Lessons on Maven that intrigue you - scroll the topics at the top. Yes, I work there. No, this isn’t sponsored. A free, 30 minute tactical workshop is a great way to get back in the swing of learning without getting overwhelmed.

Half the battle of starting to learn is doing it in a way that fits into your schedule and available energy reserves.

3// Be more than your job

Decide who you are. Write your positioning statement using this fill in the blank template. Don’t just read through it and tell yourself you know the answers - force yourself to write them down. It’s harder than it sounds, and so worth the effort.

This is not about what you do - this is about who you are. If this is hard, it should be. If you’re feeling brave, share yours in the comments section.

Fill in the blanks:

My superpower is [what you believe to be your superpower] and I especially love working with [the type of people or teams you love working with] on [the types of problems you love solving or thinking about].

When people think of me, I want them to think “Oh, that’s the person who [distinct capability or perspective].”

Unlike others in my field, I bring [lived experience, background, constraint, or pattern].

I care deeply about [value, outcome, or standard], even when it’s inconvenient.

Office hours

Q: How would you approach building a community today, if you don’t have a big following?

Submit an anon question

A: fwiw, I didn’t have a following when I started OGC in 2022. If you goal is to build and scale a sustainable and high value community, you need two things:

1. A unifying identity and/or belief system: Who is your member? What do they believe in? What problem do they have? What challenge are they trying to solve? If you’re for everyone you’re for no one, so make sure it’s clear who your community is for.

2. A clear outcome or value exchange from belonging to the community: What will someone get out of dedicating their time and energy to your community? A thriving community requires input from its members, and to get that, you have to make it clear what they’ll get back in exchange.

Once you’ve got both those things written down in clear, plain language, start finding your founding members. DM them, go where they gather and share what you’re building, partner with values-aligned orgs. Guide them toward the world you want to create, and help them want to build that world with you. Be patient - it takes time.

See you in the comments (or reply to this email to say hi!),

Each week you’ll get an idea to consider and an exercise to put it into practice, plus my POV on a reader question about work. The goal will always be to push you toward more good work, because I think you’re capable of it.

Today’s idea

The time has come for us to talk about AI and how it intersects our desire to do good work. This essay took me much longer than my normal week to write, because this shit is, philosophically, extremely confusing.

Here’s where I’ve netted out:

• For the world: we need to lean into our humanity with deliberate intensity, now.

• For yourself: the best way to differentiate yourself right now is through showing effort, process, vulnerability, personality, thoughtfulness, perspective, and creativity.

• For your job: the job market is going to be ugly while we stumble toward a new normal, and your unique collected context + how you’re perceived by others will help keep you employed.

1// we need to lean into our humanity with deliberate intensity, now.

AI is extraordinary. It will make us faster, clearer, and more capable than we’ve ever been. It’s also insanely dangerous if it dulls us down to being its mouthpiece.

The future I hope for is one where we harness AI as a tool to create better outcomes by multiplying our ability to positively influence the world around us.

The future I do not hope for is one where we default to the direction of LLMs, outsource our strategic thinking, or forget how to dream up something so crazy AI would never recommend it.

We’re at a point of divergence between these two futures, and it’s our job to collectively push things in the right direction. To do that, we need to reinforce the importance of the role of the human mind in all its strange glory, in work and in life, with vigor, urgency, and certainty.

2// the best way to differentiate yourself right now is through showing effort, vulnerability, personality, thoughtfulness, perspective, and creativity.

LLMs have, unfortunately, rendered your outputs largely uninteresting. Anyone can create an output in minutes now - polished, organized, professional.

It’s now your inputs that are interesting - how’d you think of an idea? Where did you find inspiration? What worked and what didn’t as you were building or creating something? Which of your experiences or perspectives crafted what eventually became the output?

I want to acknowledge that sharing your inputs, vs. your outputs, feels completely unnatural. From a very young age we were asked to do homework in private, and submit a completely finished, perfect product for grading. The tables have turned, and now you’re being graded on how you approach your homework vs whether the homework is correct.

Take comfort in sharing unfinished thoughts - no one thinks you’re perfect. In fact, they want to see that you’re not, because it’ll make them feel more secure in their own imperfections. To stand out and catch people’s attention, the time has come to lean into the work-in-progress version of yourself that highlights your special, unique brain and creative, earned perspectives.

3// the job market is going to be ugly while we find a new normal, and your unique collected context + how you’re perceived by others will help keep you employed.

Your productivity is no longer your edge. Neither is your fact retention or your data analysis or your volume of output.

Your employability edge is twofold:

• your differentiated collected context - all the stories, learnings, connections, and experiences you’ve gathered throughout your life, and how they position you to think differently than everyone else in your role or field.

• your personality and how it feels for others to work and create with you.

I do not know what the future of work looks like, but I’d bet my savings that humans will continue to value humans who are enjoyable to work with and bring a unique perspective that might give their company a leg up against competitors.

If AI compresses informational advantage, then reputation, trust, and community hold exponentially more weight.

Figure out what makes you unique, and start to get comfortable standing out instead of fitting in.

In practice

The real practice here is in making the non-obvious, more effortful choices across work and life. Embrace friction and effort, and place more focus than usual on your process than your output. It’s going to feel strange, until it starts to feel familiar and comforting.

This is the worst AI will ever be, which means it will only get more and more tempting to use it for everything. Instead, explore where you can make your unique POVs, experiences, personality traits, etc obvious, differentiating, and liberating.

Some thought starters:

• Instead of checking in with a connection using an AI generated email out of your life CRM, send a text with a photo of something that reminded you of them.

• Instead of looking for affirmation or summarized bullets from your favorite LLM ahead of performance reviews, take a few coworkers to coffee to understand how you can be a better partner.

• Instead of asking AI to edit your writing to make it ‘clearer’, find a peer editor to give you feedback, or put your own editing hat on to maintain your voice and make sure you don’t sound like a psycho robot.

• Instead of posting an LLM approved story arc on Linkedin, share your experience the way you’d tell someone about it over coffee.

• Instead of scrolling an algorithmic feed of what a data set thinks you want to consume, deliberately go off your beaten internet path to discover new topics, creators, or information that it would never serve you.

• Instead of getting overwhelmed with unlimited food delivery choices from ghost kitchens, ask a few friends for their favorite restaurants in the area.

• Instead of starting with a list of topics AI suggests, allocate some additional brainstorm time for you to reflect on what topic you feel most compelled to start with.

• Instead of learning a little about a lot, go deep on an obsession or curiosity.

• Instead of asking AI for career advice, send the scary email and ask a human you respect or admire.

We’re all on this journey together, and I’m figuring it out right alongside you. Have these conversations with your peers, your friends, and your mentors - we’re stronger and more confident in community.

Office hours

Q: When should I leave a stable but soul sucking job?

submit an anonymous question for a future issue

A: The annoying (but true) answer is, it depends.

On the one hand, stability is important - in order to take risks, you need a solid foundation both financially and mentally. Stability provides you with a playground to experiment and to get things wrong along the way with more upside than downside.

On the other hand, in my opinion, no amount of financial stability is worth losing or sacrificing who you are. You only get to do this life once.

Re-center yourself on what your goals are - not a role or title, but a type of life you want to have. What are all the paths that can get you to that life? Is there another one available to you now that would protect the integrity of your soul? Take that one.

See you in the comments,

Each week you’ll get an idea to consider and an exercise to put it into practice, plus my POV on a reader question about work. The goal will always be to push you toward more good work, because I think you’re capable of it.

A note: comments are now turned on! I was initially a little scared of you all, but you seem pretty nice, so let’s give it a try. Invite your friends - I’m excited to hang and talk about work stuff.

Today’s idea

Stop telling yourself that you hate sales, you’re bad at sales, you don’t like sales people, or that you’re not a sales person.

You’re selling your differentiation, skills, and promise when you interview for a role.
You’re selling a better company future when you pitch something at work.
You’re selling a hypothetical happy ever after when you go on a date.
You’re selling an ROI positive outcome when you negotiate with a service provider.
You’re selling a reward when you ask your children to follow a rule.
You’re selling your insights and POVs when you post your thoughts on the internet.
You’re selling the value of your friendship when you host a dinner party.
You’re selling a narrative and status when you get dressed in the morning.
You’re selling your vibes and personality when you choose a profile photo.
You’re selling your contributions and ideas when you ship code, or when you give a presentation, or when you deliver a project.

Selling is one of the single most powerful skill sets to cultivate, and I’m willing to bet you’ve crafted somewhere between a neutral and negative narrative around needing to sell to people.

Today, we stop that, and instead we embrace that selling is a critical life skill that we should be taking seriously and working to master.

This is going to feel like looking at your bank account, or weeding your lawn. It feels much easier to just ignore it, but the upside of staring it straight in the eyeballs and doing something about it is very high. Okay deep breath here we go.

Selling anything, in my opinion, is composed of three core elements:

1. Developing a clear set of goals

   Your outcome is the point. A mutually beneficial outcome is the goal.

   Sometimes your desired outcome will be specific (ex. I want to save 20% or more on my cable bill, I want to be hired for this specific job, I want to be asked on a second date), and sometimes you desired outcome will feel squishier (ex. I want this person to leave this conversation feeling like they respect me, I want this person to mention my name in rooms I’m not in, I want more podcast guest spots, I want to be better understood by my social following).

   Either way, your desired outcomes need to be clear and written down (philosophically or literally), because they are what informs the next two puzzle pieces of selling effectively.
   

2. Understanding who you’re selling to
   I am one of the only people I know who uses my college degree every single day. I studied a variety of psychology disciplines (child, teen, abnormal, consumer, organizational) and it has made me a top tier seller, despite my personal brand having absolutely nothing to do with sales (hopefully).

   These are the questions you should be actively seeking to be able to answer about the person, team, or entity you’re selling to, in any scenario:
   

   • What are they afraid of or worried about?

   • What do they naturally gravitate toward talking about?

   • What type of energy are they bringing to this interaction?

   • How are they rewarded? What are their goals?
     

   When you can answer these, you can much more easily and deliberately craft a story, narrative, pitch, or interaction that is tailored toward a mutually beneficial outcome.
   

3. Packaging what you’re selling

   This is, in my opinion, the fun part (I’m a brand building gal what do you want from me?). Remember this recent WSJ article that got everyone all ruffled about how storytelling is important again?

   You’ve been storytelling your whole life. Storytelling is selling. Everything is sales.

   This is the step where you take the inputs from #1 (your clear goals) and #2 (the intricacies and nuances of this specific second party) and you stop thinking so much about yourself.

   The golden rule does not apply here - do not sell to others as you’d like to be sold to.

   The key is, instead, to sell to them in a way that solves their problems, reduces their anxieties, and positions your proposed outcome as a solution, not a task.

Let’s talk through two examples.

Scenario 1: You want someone to introduce you to a hiring manager to help you get an interview.

Step 1: Your goal is to get an interview. A mutually beneficial outcome is that you get the interview, and the person who introduces you gains social capital for sending them a good candidate and staying top of mind with their connection.

Step 2: This person is a professional who’s building their network. They are someone who wants to be taken seriously, and also seen as a valuable professional connection. They worry that they’re not top of mind for people in their space.

Step 3: Package your sell as a solution, not an ask. By forwarding your ask, they are sending a highly qualified candidate and staying top of mind in their network. You’re making it lightweight, and therefore high ROI, for them by including a forwardable.

‘Hi X, I saw you’re connected to Y and I’m really interested in this role they have posted. I’m a particularly good fit for these reasons [reason 1, 2, and 3], and I’d be so appreciative if you’d be willing to forward my interest along. I’ve included a forwardable below - please let me know if there’s anyone in my network I can introduce you to in return, now or at a later date.

Here’s a real life example that I sent back in 2022 to a very light connection (hi Stephanie thank you!!) in hopes of getting an intro for a role, which ultimately resulted in my hiring at Mercury. Don’t worry about what the second one was mind ur business!!

Scenario 2: You want your manager to approve your proposal to solve a current user growth stagnation issue.

Step 1: Your goal is a stamp of approval/green light to move forward, plus confidence in your plan from your manager. A mutually beneficial outcome is that they also feel a sense of relief and optimism, because you’ve come up with a good plan that should get them closer to their goals or metrics at work as well.

Step 2: They worry about not hitting their goals at work, and not having enough proof points of wins at their next performance review. They worry they’re a bad manager because their team isn’t making a big enough mark at the company, and that would be their fault. They worry about how they’re perceived by their reports, their peers, and their leadership team. They are a high energy manager that reacts well to strong creative ideas, but needs data to back up decisions they make. They love a meme.

Step 3: Let’s sell the shit out of this plan as if it came from your manager’s own soul. We know they need data in order to confidently make decisions, so we’ll set the context of the proposal in data - what is the current state, what is our goal, and what will it take to make up that delta?

Then, we’re going to show them exactly what the end state will be (hitting our goals, yay!) with clear milestones between now and then. We’ll include some baseline ideas that feel obvious and reliable, and we’ll include a few exciting, creative ideas to test the waters on new strategies.

We’ll include the right number of memes - maybe one in the intro slide, and one to celebrate the awesome outcome we’ll get. I know, memes are cringe, but they like them so we’re doing it.

We’re going to finish this doc or meeting with a clear ask for a stamp of approval, and a short discussion about any remaining concerns they have. Finally, we’re going to give them a nice clean summary that they can share with their manager in their next 1:1 to show progress and drum up some excitement.

In practice

Let’s undo the story you’ve been telling yourself about sales.

1. Write down three situations coming up in the next two weeks where you want or need something from another person (ex. a meeting decision, an intro, a yes, a second date, more engagement on a post, a boundary respected, an opportunity, etc.)

2. For each situation, finish this sentence honestly:

   “The story I’m telling myself about selling in this situation is…”

   
   Examples might include ‘I don’t want to be annoying’, ‘they’re too busy for me’, ‘if I were better, I wouldn’t have to ask’, etc.

3. Now rewrite each story as a mutually beneficial outcome, using this frame:

   “If this goes well, the outcome for me is X, and the upside for them is Y”

If you can’t quite articulate the potential upside for them, keep thinking. Go back to the goal and the person’s nuances and intricacies and motivations and concerns. Selling gets easier the moment you stop centering your own discomfort and nerves, and start centering the shared positive outcome.

What do you have coming up that you’re going to try this for? Share in the comments, I’ll weigh in.

Office hours

Q: Do I have to quit my job to have a portfolio career?

submit an anonymous question for a future issue

A: No.

Having observed the rise of the portfolio career over the past couple of years, I’ve been fascinated by how quickly it’s become synonymous with quitting your full-time job in pursuit of agency and freedom.

Trend wise, portfolio career has recently became a new label for two general scenarios:

1. Having been laid off, needing more time flexibility for family or mental health, or fighting an unquellable (apparently this isn’t a word but it is now) entrepreneurial spirit, and thus choosing to leave FT in pursuit of working for oneself.

   Usually one revenue stream doesn’t replace a W2 salary + benefits, so it’s common that these folks take on two or three. Voilà, portfolio career.

2. Having a side hustle, but not liking the word side hustle. Once again, voilà portfolio career.

In my opinion, a portfolio career is much simpler and more accessible than the common narratives make it out to be - it’s that you make money doing multiple things.

These things can be obviously related and interwoven (like the 5 Cs framework Amanda Goetz popularized), or they can be completely discrete and live in their own worlds.

They can be carefully planned, or they can be completely accidental.

You can be doing multiple things because you have to, or because you want to.

You can work entirely for yourself, or you can work entirely for other people.

You can make it work for you with a cohesive narrative to further emphasize your personal brand, or you can hold multiple completely different identities - maybe you even have a stage name or a pen name!

You are simply taking the hours you have available for work each week, and deciding what to do with them.

I don’t have kids and I really love working, so I have more hours ‘available’ than many. As such, I’m able to dedicate 40+ hours/week to my full time job, plus an additional 10-20 to other projects like this substack, my membership community, and advising/consulting.

For those who have 20-40 hours to dedicate, their portfolio will look different. Same for 0-20. Same for the ones who don’t sleep and chill in that 70, 80, 90 or 100 range.

You can have a portfolio career without quitting your full time job. You also don’t have to have one at all. But, in my humble opinion, more money, control, and ownership is nice, especially if you can make it doing something you really enjoy.

See you in the comments,

Each week you’ll get an idea to consider and an exercise to put it into practice, plus my POV on a reader question about work. The goal will always be to push you toward more good work, because I think you’re capable of it.

Today’s idea

Can you hear it? Our parents and our teachers cautioning us against being easily influenced when we were kids? Telling us that just because Timmy said something was cool didn’t mean it was? It’s time to grow past that, because opening yourself up to being influenced by the people and the world around you is one of the fastest unlocks to a high growth, discovery-led life.

Consider new ideas and perspectives you read here on Substack. Invest in conversations you have with peers, leaders, and strangers - ask follow up questions. Investigate and dig deeper into content you consume. Delight in and test new technology, and try on new possibilities. Soak up new environments and norms you find yourself in. Treat art, music, culture and trends as important inputs into your work. Change your mind about things you used to think were true.

At a certain point, you need to let your curiosity and a willingness to evolve triumph over protecting an identity you created and adopted in outdated circumstances.

The key is not to be influenced any anything and everything, but instead to identify and separate your core belief system from your working belief system. Then, you can hold your core system close while pushing your working system to adapt over time based on new information.

Your core belief system are your values, and your values are your filter as you internalize new information. For me personally, these values include doing no harm to others, favoring progress over tradition, creating strong community systems, measuring value beyond dollars, etc.

Your working belief system is your POV on the current world around you, particularly when it comes to work. With all the information you have, what do you think is currently important? What can you de-prioritize? What skills should you invest in learning? What does good look like in your field? What’s the highest impact work you can be doing? etc.

I recommend the following framework each time you encounter an interesting new perspective or piece of information:

Step 1: Parse
The human brain can only consume a few pieces of information at once - choose the ones that apply most directly to your daily life. For example, if you attend a panel with thought leaders in your field, you’ll need to parse through everything they say to pull 3-4 key messages or takeaways out.

Step 2: Evaluate
Take those 3-4 nuggets and evaluate them against your working system and your core system. Where do they align? Where do they conflict? If they conflict with your existing systems, have you developed conviction that you should shift your working system to include this new information?

Step 3: Integrate
Update your working system with the new information. It’s like a software update! Sometimes software updates are nearly unnoticeable, and sometimes they really fuck your shit up. Either way, they’re important.

It’s cool to evolve. It’s interesting to be well informed. It’s compelling to be able to cite a variety of examples to support your beliefs. It’s admirable to change your opinion. Be willing to be influenced.

Share Good Work

In practice

You’re not trying to become impressionable; you’re learning how to let new information touch you without destabilizing who you are.

1. Notice what affects you

   For the next 24 hours, pay attention to the moments that shift you.

   • Something that makes you pause, feel curious, rethink an assumption, or feel energized

   • A line you highlight, a comment that sticks, a song that changes your mood, a conversation that lingers

   
   At the end of the day:

   • Write down 3 things that influenced you.

   • Note the format (conversation, writing, video, environment) and the feeling it created.

   
   Practice noticing what gets through your filter.

2. Map your influence patterns
   Your taste leaves clues. Make a quick list:

   • 3 people whose work reliably shapes how you think

   • 3 pieces of media you return to regularly, or have returned to recently

   • 3 places (digital or IRL) that inspire you

   
   Then ask:

   • What values or themes connect them?

   • What kinds of ideas seem to influence your working beliefs?

   • What ideas or perspectives never land for you and why?

3. Practice being influenceable

   Choose one input this week that you’d normally scroll past or dismiss:

   • A perspective outside your industry

   • A creator with a different background or style

   • A tool, format, or idea you’ve been skeptical of

   
   Run it through the framework:

   • What’s worth integrating or considering?

   • What doesn’t belong in your core or working system?

   • What small update could this prompt in how you work or think?

Hold your values steady, let your working beliefs stay flexible, and you’ll know exactly how to let the world influence you without losing yourself.

Office hours

Q: What is your take on being “professional” vs. being “authentic” at work?

submit an anonymous work question

A: Being “professional” and being “authentic” aren’t opposites. Professionalism is just the skill of expressing your authentic self in a way that respects context, power dynamics, and the people around you.

Authenticity isn’t about unfiltered self-expression or saying everything you think; it’s about alignment with self. When your values, perspective, and behavior are consistent (even if you’re adapting your tone, language, etc to the room you’re in), you build trust.

The problem isn’t authenticity at work, it’s the outdated version of professionalism that confuses credibility with emotional distance, neutrality, or sameness. Real professionalism is clarity, reliability, good judgment, and care for impact - there are plenty of ways to deliver on that while still acknowledging and expressing your personality, belief systems, and interests.

Free yourself from the goal of fitting a mold, and instead invest into learning how to bring more of yourself into the room in a way that’s useful, legible, and constructive.

Until our appointment next week,

Each week you’ll get an idea to consider and an exercise to put it into practice, plus my POV on a reader question about work. The goal will always be to push you toward more good work, because I think you’re capable of it.

Today’s idea

Having fun, strategically, can be a powerful differentiator.

This was the second note I wrote after joining substack, and tbh I was caught off guard by its resonance and reception.

Whenever I think of the folks I admire most - those I’d love to work with - one of their most visible traits is always that they clearly enjoy most of what they do. They enjoy it so much that they’re highly engaged, and able to spend the extra time and energy to make what they do interesting for themselves and others. They’re constantly challenging themselves and experimenting and sharing their delight in their work with the world around them.

Now, it would be #verybadadvice if I said you should only work on things you love - as we all know, that’s a pipe dream. Where I’m actually going with this is that you should invest time and energy into finding ways to have fun in the work you already do.

Can you integrate more of what you love into what you do? Can you test new versions of your work that pique your curiosity vs just going through the motions each day? Can you use fun examples instead of serious ones to illustrate your points? Small moments of delight throughout your days can add up to big change - both in how you feel, and in how those around you perceive you to feel.

Enthusiasm and curiosity are contagious, and they make people want to help you and work with you. Where can you spark those moments for yourself using the frameworks and resources that you already have? And then, how can you share that enthusiasm and curiosity with those around you?

Our goal is not 100% fun (again, a pipe dream) - it’s to move your work minutes from 2% fun to 15% fun.

That extra 13% fun will meaningfully differentiate you from those who have come before you, and from those who are competing with you for the same opportunities, awareness, exposure, clients, business, etc.

In practice

Sometimes, we’re so deep in it that it’s hard to even imagine what fun at work could look like. Here are three prompts to explore that for yourself:

1. How did you willingly spend your free time as a kid and teen?

   How can you integrate the essence of those activities into how you approach your work now?
   ex. I spent my childhood free time collecting things, sharing my passions with adults, trying to understand others, and reading. Most of my work fun today comes from curating information, sharing my interests with adults, trying to understand and help people, and reading/reflecting on other people’s work.

2. Name 2-3 projects or moments at work (ever) that you enjoyed, either because they were fun to do or because you found what you learned really interesting.

   What themes and through lines can you observe about those projects so you can prioritize doing more of them?
   ex. Maybe you really enjoyed a project you did with a specific person - what made that project fun? How can you replicate that? Was it because the person was fun, or you two came up with a version of the project that was more interesting than the generic version?

3. Choose 1-2 things you do at work that you could have more fun with or reinvent in some way.
   What outputs can you make more engaging for stakeholders? How can you add some color or stories or creative ideas to brainstorms or deliverables? How can you help others enjoy their days and work more?

   Think:

   1. Presentations

   2. Research projects

   3. Docs and writing

   4. Communication with peers

   5. Content & sharing

   6. Community building with coworkers or customers

   7. Mentoring or managing

   
   ex. Use fun and relevant examples. Inject a joke or two. Use your speaking voice vs your academic or work-coded voice. Share your perspectives in addition to the facts. Use a color!

Office hours

Q: How can I make a career pivot or change my situation without starting over?

submit an anonymous work question

A: We need more language around career pivots. A pivot implies a very significant redirection, and career adjustments don’t always need to be so dramatic to be effective or impactful.

I’d like to propose a new framework:

Career wiggle

A career wiggle is a small, low-risk adjustment inside your existing lane - career wiggles are great for maintaining interest and momentum without having to reinvent your professional identity or narrative.

Think: slight shifts in role scope or focus, keeping the same role/title but in a new industry, or adding a side project to explore new territory.

Career shift

A career shift is a directional change without a full reset. You’re carrying skills and leverage from your past work, but applying it in a new context. This might look like joining an adjacent team at your company (ex. marketing → product marketing), shifting from full time to fractional or freelance, or investing in part time education to learn a new, complimentary set of skills.

This is where storytelling becomes especially important - how can you find and articulate the through line between what you were doing before and what you’re doing now? What was the why for the shift?

Career overhaul

A career overhaul is a clean break. You go back to school, you claim a new path, you start from the beginning in a new world. Your prior experience may help internally, but externally you’re rebuilding credibility, identity, and momentum.

Overhauls tend to be emotionally taxing, extremely humbling, and usually well worth it, but this is definitely the ‘feels like starting over’ category.

Now that we have more language to work with, what can you do in terms of a wiggle or a shift before you commit to an overhaul?

Until our appointment next week,

Today’s idea

Our mortality! Specifically, the concept of memento mori, which translates to ‘remember you must die’.

You may not love considering your own mortality or the fragility of life, but I encourage you to give it a shot. I faced dying at 25 with cancer, and my comfort with my inevitable death has been my unfair advantage ever since - particularly at work.

We benefit from having default patterns, shortcuts, and filters to run our lives through; they help us process and understand things, and create clarity and confidence as we make hundreds of choices each day.

Memento mori is one of my favorite filters, because it creates a high and clear bar for how I spend my time, much of which is spent working. It reminds us of:

• The impermanence of it all: You, your career, your company, that feature you built, the money you make, that list you made it onto - none of it lasts forever.

• The value of our attention: Time is limited and unpredictable; how you spend it matters. Where you dedicate your attention is what fills your world.

• Our agency and free will: You don’t control how long you’re here, but you do control the choices you make. You can change almost anything at almost any moment.

When you apply the concept of memento mori directly to your work life, things can initially look bleak.

Tippy-tapping on your keyboard to make some guy or some brand some money probably isn’t going to land in the ‘this is a great use of my time’ bucket, but this is where we need the discipline to push a step further.

Consider the second and third order impact your time at work is creating.

• Are you or your team creating things that bring people joy or comfort?

• Are you helping create access to resources or knowledge?

• Are you creating financial stability for yourself so you’re able to spend time and energy helping your community or causes you care about?

• Are you supporting your coworkers’ growth toward a life they’re proud of?

The work itself isn’t usually where you’ll find your impact or fulfillment - it’s in the second and third order effects of your time contributing to a larger system.

Consider the systems you’re perpetuating, and apply memento mori here. Are you moving the world in a direction you like with your work?

In practice

We’re going to write our obituaries today (but that’s so0o0o dark - I KNOW, but often finding light requires darkness, sorry!!).

Assume you die this week. Freak accident, peaceful passing, whatever you like. Write three obituaries for yourself from the following perspectives:

• A close friend or family member (choose someone specific)

• A coworker (choose someone at or related to your current role)

• Someone who didn’t know you personally but was aware of you on the internet

Write them in the following format:

I knew [your name], and they were ____, _____, and _____ [three adjectives].

They spent their time doing _____[how they knew you to spend their time] and I think the world will remember them most for _____[the impact they perceived you to make].

They made me feel _____[how you imagine you, on average, make them feel]

After you’re done writing, walk away for a few hours. Return later and read them - pay attention to how they make you feel in your heart in addition to how your brain responds.

If you’re feeling lackluster, or like they don’t fully represent everything you know you’re capable of creating in this world of ours, consider what would need to change for that to be different. LMK how it goes - you can reply to this directly.

Office hours

Q: Do you think that “dream jobs” are real? When we were younger we were always asked what we dreamed of being when we grow up. But now that I’m grown up, frankly I’ve become quite cynical that it’s impossible to have a dream job if you work for others.

submit your anon work therapy question here

A: I think of dream jobs the same way I think of soulmates. I believe in them, but I think the media did us dirty in setting the wrong expectations.

We were told that a dream job was your favorite hobby or passion reincarnated into a job that would pay you enough to live a comfortable and fulfilling life. I believe a dream job is an arrangement where you:

• do work you enjoy and are good at,

• with people you respect,

• where you’re learning new things,

• making enough money to fund a comfortable and fulfilling personal life,

• with enough free time to enjoy that personal life.

With this framework, it’s actually very possible to have a ‘dream job’ while working for others. Working for others can be really great, if they see the world through a similar lens to you.

In my experience, the jobs I’ve had the most friction in have involved differing belief systems between myself and the person/company I’m working for - when you solve for that, many other elements of this equation tend to fall into place.

This framework is also a case, for some, for a portfolio career. Portfolio careers can include full time roles, or can be a mix of PT projects that culminate in the situation above. They’re great because they give you more control over each of the equation pieces individually. They’re hard because they sometimes lack security and predictability.

My tldr advice is to consider aspiring toward a dream life, rather than a dream job. A dream life might include a ‘boring’ but healthy role that enables an incredible existence outside of that role, filled with passion projects, community building, self care, and exploration.

Until next week,

I hope it’s comforting that we’re all here in the strangeness of figuring work out together. The good news is that strange things have happened before, and they’ll happen again. The bad news is that this time it’s robots, unemployment, and existential crises.

I wish I had the answers, but alas, all I have for you today is a collection of Linkedin posts. I was feeling nostalgic and took a look back at the ones that got the most engagement this year, then realized it might be helpful to gather them all together for you.

Future Good Work issues will be more ✨structured and topical✨starting in January, but hopefully this will hold you over until then.

Before you dive in, please indulge my advice column dreams and submit a question about work (deliberately broad) for me to weigh in on in future issues.

Submit a question

Thanks! Now onwards to these posts - I hope they’re helpful as you enter this season of planning, reflection, and cheese. Read to the bottom for some bonuses!

Click the headlines to read the original posts and comment sections (lots of added value in comments sections imo).

1. OpenAI is positioning themselves with the same ads playbook we used at Pinterest in 2013.

   If I’m honest, I was shocked this was my top performing post from this year - I fired this one off in 5 minutes before I went to bed one night after a conversation with a previous Pinterest coworker.
   This is your reminder that you are the product on any platform you don’t pay for (and on many you do). Your intent data is the highest value data they can have. When this is the business model, the goal is to keep you on platform for as long as possible to get your eyeballs on as many ads as possible. Keep this in mind.

   
   

2. Keep track of job boards other than Linkedin - the ones in your areas of expertise, passion, and industry.

   Job boards are one of the best ways for you to keep a pulse on the future - yours, and the future of the spaces you work in. Where are companies investing their dollars via salaries?

   *I’m including a list of more job boards I’ve collected since sharing this post at the end of this post.

   
   

3. Send the scary email. (this one even ended up in the press!)

   The worst thing that can happen is usually nothing. Expanding your surface area for luck and connection will accelerate your career more quickly than most playbooks. Scary emails have literally built my career brick by brick. Don’t forget it’s a human being on the other side.

   
   

4. What makes a good resume? (bonus post: resume do’s and don’ts)

   Make it skimmable, relevant, curated, visually clean, and reader-friendly. Do yourself and your unique set of experiences justice. For the love of god include your linkedin url and no more than a 2 sentence summary. Don’t make the hiring manager do extra work to interpret why you’re a perfect fit.

   
   

5. How candidates are standing out and getting interviews
   This one also includes some tips on how to make your resume work for a hiring manager’s review flow, in addition to navigating warm introductions and cold outreach. I did a lot of hiring this year, but these are the opinions of one.

   
   

6. Why I joined maven, and how it fits into my broader aspirations
   While this was mostly an announcement post of my new role, it might also help you consider how a full time job could fit into a portfolio career vision. (a lot of folks incorrectly assume that a portfolio career can’t include a full time role)

   
   

7. Finally getting comfortable with being seen on the internet
   There’s something really challenging about the internet as a mirror, and its way of making you hyperaware of how you’re being perceived. I made some progress here this year and I hope you did too.

   
   

8. It’s never too late to blow it all up
   I blew everything in my life up at the apparently extremely old age of 29, and turned out much better because of it. Think of your life in decades and trust your instincts.

   
   

9. A 35th birthday reflection - your early career is comprised of 3 five-year periods.
   This became a neat and tidy working theory of mine this year - your early career can be divided into ages 20-25, 25-30, and 30-35. Each phase serves a purpose, and leaning into these seasons creates opportunities for growth.

   
   

10. Battle of the brands: GPT vs Claude
    Who remembers the great thinking cap rush of 2025? The team at Anthropic reminded us that we humans like to virtue signal, and that we do indeed hope our humanity wins over the robots. Suddenly every tech brand was hosting IRL coffee shops to capture the magic of people making eye contact.

And here are a few bonuses that I loved but the linkedin algorithm didn’t:

Consider setting lifestyle goals rather than title or compensation goals

The layer between friends and strangers

Are you unhappy, or are you unhappy with how others perceive you?

A gratitu-do list

Specialized generalists vs generalized specialists

The skills you should be developing right now

*some additional job boards 4 u:

Builtin.com
Wellfound.com
Hiring cafe
Welcome to the jungle
ilovecreatives
Getro
Power pause flex jobs
Idealist (nonprofit roles)
On Purpose (social impact roles)

See you in January!! Say hi. Happy holidays💫