Most of us are approaching the 2026 job market and application process all wrong. Rather than try to fit into the box of whatever the latest job post is showing up your feed, I am going to offer a new radical approach to unlocking career that actually fits who you are.
This is a long, but hopefully fun read that brings back that hop in your step. If you are feeling stuck right in your job or unsure of what to do next, you are not alone. 50% of the workforce is made up of quiet quitters, and with that over 50% of the workforce is ACTIVELY looking to make a career pivot across industries and generations. (Insane!, I know.) Many are feeling hopeless, overwhelmed, anxious, depressed. I have been there, and know exactly how you are feeling. The guilt, the shame…it’s all consuming.
This is a 4-step plan that worked not just for me (Makena - the Founder of oyster, prior to launching oyster), but my friend who got a job at Google, and my colleague who landed a job on the innovation team at Pepsi. I shared this plan to multiple classrooms full of NYU Stern (my alumni) students — both undergrads and grad students. While geared towards corporate career people, this is a plan that’s applicable across industries and roles.
The craziest thing about the plan is that it is about doing less not more. I took a lot of inspiration from the Essentialism book which is all about going deep on the things you care about. Shifting from: filling out 100 job applications —> being persistent for the top three organizations you care about. This is a plan that will likely help you get the job without even applying to the job.
With that said, let’s get into the plan….HOLD ON TO YOUR HATS!!!!
Step 1: Get seriously curious about what lights you up.
What industries excite you??? If you are stuck, think of your favorite classes in school, spaces or trends you’re intrigued by, problems you genuinely care about, even things that drive you nuts or make you angry in the world — that’s a sign you are passionate about it! For me, with my soon to launch company oyster, it was the technology industry, specifically social media (today’s platforms are divisive, addictive, and negative) and the all consuming what-the-f-do-I-do-about-my-career question. I also realized I was using LinkedIn in a way it wasn’t intended, which is what sparked the general concept and feature set of oyster. If I had stayed the corporate 9-5 path, I loved the media industry, and thinking about how legacy players like Disney could leverage emerging technology. Here is a list of the core industries, try to identify your top 1-3:
- Agriculture & Environmental Systems: Cultivating sustainable food sources and protecting the planet’s ecosystems.
- Automotive & Transportation: Driving the future of mobility, logistics, and vehicular innovation.
- Aerospace, Aviation, & Defense: Advancing flight technology, space exploration, and national security systems.
- Chemicals & Materials Science: Engineering the foundational compounds and advanced materials that power modern products.
- Mechanical, Utility, & Technical Services: Maintaining and optimizing the critical machinery and infrastructure that keeps society running.
- Consumer Goods, Fashion & Retail: Designing, producing, and selling the lifestyle products and trends that shape daily life.
- Education, Libraries, & Museums: Preserving knowledge, inspiring curiosity, and shaping the minds of future generations.
- Energy, Sustainability, & Climate Solutions: Powering the world while pioneering clean energy and eco-conscious innovations.
- Financial Services & FinTech: Managing capital, protecting wealth, and revolutionizing economic transactions through technology.
- Healthcare & Public Health: Enhancing patient well-being and safeguarding community wellness through medical care and advocacy.
- Hospitality, Recreation, & Tourism: Creating unforgettable experiences, leisure activities, and world-class service for travelers.
- Insurance & Risk Management: Analyzing potential hazards to protect individuals and businesses from financial uncertainty.
- Legal, Policy & Advocacy: Upholding justice, drafting regulations, and fighting for the rights of individuals and organizations.
- Life Sciences & Biology: Studying living organisms to unlock breakthrough medical treatments and biotechnological discoveries.
- Media, Design & Creative Arts: Shaping culture and telling compelling stories through visual, digital, and written expression.
- Industrial Operations, Manufacturing, & Resources: Scaling up production and managing the supply chains of raw materials and finished goods.
- Real Estate, Housing, & Community Development: Building communities and managing property markets to create places people call home.
- Technology, Data, & Innovation: Developing the software, systems, and intelligence that dictate the digital age.
- Government, Global Relations, Non-Profits: Serving the public interest, fostering international diplomacy, and driving mission-based change.
- Construction, Architecture & Urban Planning: Designing and constructing the physical spaces, buildings, and cities of tomorrow.
- Business Services & Consulting: Advising organizations on strategy, efficiency, and growth to optimize their performance.
- Anthropology, Archeology & Cultural Research: Unearthing human history and studying cultural behaviors to better understand our society.
- Culinary Arts, Food & Beverage: Transforming ingredients into exceptional dining, drinking, and hospitality experiences.
- Crafts, Skilled Trades, & Artisan Work: Preserving specialized, hands-on mastery to build, repair, and create bespoke goods.
- Sports, Fitness, & Athletics: Promoting physical wellness, teamwork, and entertainment through athletic excellence.
- Social Impact & Human Services: Supporting vulnerable populations and providing essential resources to uplift local communities.
After identifying your top 1-3 favorite industries, have a think on the types of organizations that best suit your style:
- Public Companies: Large-scale entity publicly traded on a stock exchange. Larger and with that more slow moving, which can be good and bad in that they tend to offer more work-life balance (than say a startup) and have a clear corporate ladders/structure, but with that there is often greater bureaucracy.
- Private Company: For-profit companies not on the exchange. Best for those that don’t like to deal with public company corporate politics, prefer more fast-paced, get-what-you-put-in, innovation forward environments. Startups fit in this bucket.
- Nonprofit: Charities, foundations, and social enterprises. Best for those that value non-partisan global impact.
- Governmental / Public Sector: Federal, state, or local agencies. Best for those that value national impact.
- Small Local Business: Physical storefronts, mom-and-pop shops, local services. Best for those that value local, in-person impact.
- Self-employed: Solopreneurs, freelancers, and gig workers. Best for those that value autonomy and flexibility.
After identifying your favorite industry/sector (e.g. media/entertainment & technology) and preferred org type (e.g. startups), ask A.I. to generate a list of organizations in that space: “Hey Claude, please output a list of tech startups in the media & entertainment sector. Please give me an overview of each organization and link the website.” You can even add location as a perimeter e.g. NYC only or London only. [Callout: A.I. organization outputting is not great. It might require you trying Google, Crunchbase, and other sites too. oyster is going to help A LOT with this search process.] Narrow down as best you can to the top 1-3 organizations that you are most curious and passionate about. [Before even leveraging A.I., have a think yourself on organizations in that industry that light you up. Perhaps it’s a product you are already using and love, or you really connect with the org mission.]
Step 2: Be a SPONGE. Absorb newsletters, podcasts, and books pertaining to the industry and/or organizations that you like.
For me, because I was curious about the media industry I read: Disney War; Ride of a Lifetime (ex. CEO of Disney); Creativity Inc.; The Big Picture; It’s Not TV; Who is Michael Ovitz; That Will Never Work (about Netflix); Like, Comment, Subscribe (about YouTube); Year of Yes (Shonda Rhimes autobiography), and many more outside of film but business adjacent including: Steve Jobs; Pour Your Heart Into It (about Starbucks); Indra Nooyi’s autobiography (ex. CEO of Pepsi); the Glossier biography; Shoe Dog (about Nike), The Airbnb Story, Quantum Marketing (Mastercard), Conscious Capitalism, The Metaverse. If you like music there’s a book on Spotify. Books on healthcare, gaming, education, etc. FIND YOUR BOOK!
For me, media podcasts I listen(ed) to included: The Town (personal fav), Rewatchables, The Big Picture (basically anything from The Ringer). I also subscribed to The Puck newsletter. There is a podcast and newsletter for EVERYTHING nowadays, find your industry specific podcast. Btw technology has never been more relevant and is applicable to every single industry, in which case I would highly recommend everybody start listening to The Vergecast with Nilay Patel.
Being a sponge - reading up and listening to podcasts - is a way to start to build a perspective on the industry and space it is you are passionate about. Both its current and future state. Stay abreast of market and tech trends, and how the top three organizations on your list are responding.
Step 3: STOP APPLYING TO JOBS - start coffee chatting it up!!!
Once you have identified your top 3 organizations, get busy on LinkedIn. Invest in Premium. And once oyster launches in June, quit your $49.99 a month LinkedIn subscription and use oyster for $9.99 a month.
Dropping a screenshot of some of the outreach I did on LinkedIn over the past 8 years:
Since 2018, I’ve probably cold DMed over 100 people easily. At Disney, Netflix, sweetgreen, Airbnb, emerging tech startups in the film space, Roblox, Epic Games. Even when I absolutely loved my job at frog Design, I was ALWAYS coffee chatting people at cool companies in cool roles, and following up with my favorites. I coffee chatted like it was hot. Shooted my shot like I had nothing to lose.
Here are two different options for your initial outreach (your welcome). Remember to keep it short and sweet:
OPTION #1:
“Hey [NAME]! I am sure you are incredibly busy, but I would love to treat you to coffee to learn more about your experience in [INSERT ROLE] @ [INSERT COMPANY] whenever your calendar permits!”
OPTION #2:
“Hey [NAME]! No doubt you are extremely busy, but I came across your profile and see you’ve had such a unique trajectory. Would love to learn more about your pivot from [NAME OF COMPANY OR INDUSTRY] to [NAME OF NEW COMPANY OR INDUSTRY] and get some career advice. Do you have 15-30 minutes to spare?”
Use either of these templates, and send it to 10 people in roles/teams you are interested in at for EACH organization you are interested in, so 30 messages total. ^ Tailor your outreach to the person as best you can. FOLLOW UP after a week if they don’t respond! Try to find people who have previously worked at the organization or industry you are currently working in or share your alma mater that way you are already starting from a similar foundation — I call that a warm lead.
For the coffee chat itself, I have proprietary question guides to keep the chat candid and exploratory. These will be available on oyster. Moral of the story: Keep it all about the other person. Try to find out as much as you can about them: Where they started their career, how they approached their career, how they pivoted, why they pivoted, what they like and don’t like about the industry or organization they are at, examples of projects they’ve been on, skill sets they use day-to-day, side hustles/hobbies, and tactical how-do-I-break-into-this-industry advice. If the person you chatted to isn’t in the team or role you are looking for/feel best fit for, ask them if they can connect you to a person in that role or team. That’s the scavenger hunt piece of this step, and I did it all the time because it’s incredibly difficult on LinkedIn to find that niche emerging tech strategy team, especially within companies of over 10,000. (again, a problem that oyster will solve for)
Wrap up the coffee chat by 1) Offering something (on one coffee chat I offered to create a Los Angeles itinerary for a guy who shared earlier in our chat that he was going to LA for the first time). 2) Ask that person if they have any newsletter, podcast, or book recommendations - maybe they even have their own Substack! (because doesn’t everybody now) - and follow up on that! “Hey Bob, love this book you recommended! Thought XYZ was so interesting. Thanks for that awesome rec. By the way, do you have time for another coffee chat in a few weeks? Would love to reconnect and hear what you’ve been up to!” Make your mission building rapport, getting to know the person — NOT getting a job.
This follow up step is crucial. THIS is how you get the job - not applying online or a generic referral (although you 1000% should have a referral and should NEVER apply to a job without one) — it’s that first coffee chat, AND creating a loose coffee chat cadence every month or so. It’s being on that first interview with HR like, “Yep, I’ve also chatted with 5 people on the [INSERT TEAM NAME HERE]. I know exactly what it takes to be on this team.” THAT is how you show interest. THAT is how you stand out in the crowd. It’s the ultimate power move to list the names of the people on that team that you’ve already talked to (and that hopefully already like you)
You’ll know you’ve succeeded in the art of a coffee chat, if it organically leads to that person offering to refer you. 8/10 times it happened for me — my energy and passion for the industry/org shined through so much, that the person offered to not only refer me, but keep me in the loop on postings which is critical because so often the coolest jobs never make it to an official post.
This coffee chat step takes effort, but it’s much more meaningful and has a stronger hit rate than applying to one hundred jobs. Try to make it in-person and not virtual if you can. Yes, it’s a time and money expenditure to get coffee in-person — at the place most convenient to that person, but you have to do it. Don’t only pick the stop that works best for them (even if it’s a 1-hour commute for you), but get their coffee order in advance, and get to the spot early so that when they show up, the coffee is ready. Be respectful of time. If you say 30 minutes, make it 30 minutes. Although, if it’s a good conversation, most people will be fine to go over. If it is a virtual chat, literally offer to Venmo the person $10 for a coffee as a “small thank you for their time”
Step 4: Screw the resume, build a portfolio.
You are and have done way more than your resume. A resume is a teaser, your portfolio is the main attraction. I was a strategy consultant for five years, and I’d never heard of strategy consultants or finance people having portfolios but YES, YES YOU SHOULD. Anybody and everybody should have a portfolio. I built mine on Mural. Essentially what I did is blind the names of the clients and outline the project at a high level:
- Project objective (e.g. Help Tier One Supplier get to $200 million in recurring revenue in two years)
- My role on the project (e.g. consumer research, synthesis, first pass at slide decks, iterations, presentation, etc.)
- Break down how you approached the project/your specific tasks: “Step 1, 2, 3…” QUANTIFY IT. e.g. “I interviewed 30 SMEs in the autonomous, connected, and electric automotive space”. Show samples of the questions you asked. Showed examples of a key takeaway. This is the section your resume can’t show. It’s the enchilada — the meaty stuff.
- Identify the outcome: Where did you land? For me, being in the innovation space, it was often a solution (new product or service recommendation). Quantify the outcome. e.g. “We recommended 2 solutions harnessing the power of robotic and digital twin technologies” and “I audited 100 startups in the emerging technology automotive space using X framework, and identified the top 3 to partner with”
- Were there any new processes you come up with that helped the team move faster or get to a better outcome? If so, flag that.
In addition to building oyster, I also went the freelance path to help pay the bills in the interim. (Did you know solopreneurs make up over ONE THIRD of the U.S. workforce! Also, 44% of Americans have more than one income stream. Yep. This is not your parent’s workforce generation.) When I went freelance path, I took a pass at defining my ‘offerings’ if you will, which I put on a basic website I vibe-coded here: nocularlab.com . In addition to the website, I built out a Mural board highlighting a project that represented each of my six offerings. On that board, I also put my letter of references, a contact sheet of people who would vouch for me, and a smattering of the client logos I had previously worked with.
What you are really with this portfolio is essentially SHOWING, NOT TELLING in your interview. When you are in the interview, I want you to literally say, “Hey, do you mind if I share screen so I can walk you through some of my work instead of just telling you about it?” Interviewers salivate when you say this. Trust me. It also works as a cheat sheet for you too — that way you don’t have to memorize responses.
Once you are two to three interviews in, you should have a sense of the role and actively come forth with proactive ideas of how you see yourself fitting into the role, recommendations of things you would like to propose or explore in the role. This is more role/team dependent, but you best believe for me in the media/entertainment emerging tech space I was going after, I whipped out a deck with 12 opportunity areas that were well-researched; viable, desirable, and feasible leveraging A.I., AR, VR, and IoT technologies, personally curated to the organization I was interviewing at. What I am saying is if you don’t have projects relevant to the team/role or company you are interviewing for, CREATE them. Try to do the job before starting the job. It’s impossible to say no to a candidate like that.
Last thing to note here, if you do get rejected trying my 4-step plan, I bet you made it pretty far in the interview process, and if you did the check to make sure you are truly coming from a place of genuine interest for this organization, industry, and role then you likely have stood out in a really good way. Therefore, there is ZERO shame in the game in keeping in touch with the recruiting team and the people you interviewed with. Again, coming back to the approach of going deep and not wide. It’s in the art of being persistent, respectfully following up, checking-in every quarter to see if there are new positions, and identifying what you might do to become a more viable candidate in the interim (e.g. uncovering what new skill sets to add to your toolbox). Do not give up. You will get it eventually, and your persistence and passion make you unique.
BONUS: 10 magical, small tips & tricks that really helped me from a mental and confidence POV when activating this plan
1. Music - Dua Lipa, Tame Impala, whatever it is you love! Start your morning with music. BLAST IT!
2. Move your body and get outside every single day — rain or shine. Fresh air, fresh air, fresh air
2. Call a friend EVERYDAY, particularly in the evening (that’s when I felt the quiet quitting blues the most)
3. Affirmations - try these:
- I am smart, competent, and worthy of a job that I genuinely feel excited about.
- I am fearless. I go after what I want.
- The right organization is out there waiting for me, and is in need of me — my skill sets, my experiences, my passion, my energy.
4. Journaling every evening to get the negative talk track out and replacing it with the affirmations above instead
5. Read More Than Enough by Elaine Weltheroth. That book changed my life. Elaine is real, raw, and honest about how she struggled to figure out her career and life. Same with Bozoma Saint John - I LOVE her book: The Urgent Life. I also did her confidence workshop back in 2021 at a time I really, really needed it. Boz worked at Pepsi, Beats/Apple, Netflix. She is a corporate queen! Other must-read books: The Defining Decade, The Alchemist, The Motivation Manifesto, Lessons for the Living
6. Watch the Pixar movie Soul.
7. Scott Galloway: I don't agree with everything he says particularly about paternity leave, but he tells it like it is when it comes to young people, building a career, the economy, and the impact of A.I. He quells a lot of anxiety through facts. I also highly recommend all of his books. The top two books I would recommend are The Algebra of Happiness and Post Corona.
8. Check out another Substack post I wrote on this topic: https://makenachristine.substack.com/p/how-to-discover-what-it-is-that-you?utm_source=substack&utm_campaign=post_embed&utm_medium=web
9. oyster events coming soon will be a fun, fabulous, no bullshit way to meet with people you might be interested in and vice versa from a career POV. We are essentially helping you career matchmake. Stay tuned, and basically these 4-steps above are features in our app — discover search to find organizations, exploring by industry, finding people to 1:1 chat with, and more
10. Give yourself grace. In the grand scheme of life this moment of feeling lost and stuck is a blip of time. If you are alive, healthy, and loved — that is all that matters at the end of the day. At the same time, trust me when I say, I know that feeling of stuckness. The books in steps 5 and 7 of the BONUS section truly saved my life.
And now, you have a new plan to action — a plan that actually works. You are going to get a new role that is just as FABULOUS as you!!! It’s a matter of when, not if. Try as best you can to hold on to that abundance mindset. We spend ONE-THIRD of our life at work, you owe it to yourself to not just survive but thrive.
So homework assignment #1: What are the top industries and organizations you are genuinely curious about?
