(this blog post was originally posted on the Substack of oyster Founder & CEO, Makena)

Figuring out what you want to do with your career or even what you like can feel almost embarrassingly difficult. Why is it so hard?

Well, the reality is that we have less-than-clear career skies. Our perception of work and careers as a whole is clouded by the ingrained beliefs we’ve been carrying since we were 5-years old about the jobs that are “good” vs. the ones that aren’t. Where did we get these beliefs in the first place?

Our parents, our friends, TV (Music, Hannah Montana; the OG YT-influencer, iCarly) and film (Book Editor, The Proposal with Sandra Bullock; Media-Fashion, Devil Wears Prada with Anne Hathaway), and even our social feeds with its algorithm (TikTok, Instagram, LinkedIn) tend to show us more of what we already.

If you were to actually take an honest, sobering look at your current career aperture and network, you’d see it’s undoubtedly small: The same handful of industries, roles, and career paths. This is why it’s so damn difficult to figure out what we really want to do: we are subconsciously viewing our career potential through the limited lens of the world we grew up in and currently inhabit. It’s hard to think beyond it. (This reason is exactly why I founded oyster — a career discovery and micro-community app you can use to explore industries, roles, and people outside your periphery.)

Of course, it would be naive to suggest quitting your job to become a full-time painter without a client base, that is absolutely NOT what I am recommending in this guide. Instead, I’ll suggest something more nuanced and still practical, such as: why not actively pursue painting while strategically maintaining a 9-to-5 that helps you pay the bills and gives you the emotional headspace to pursue that painting dream? (more on this later!)

By reading this guide and applying these strategies, you will hopefully begin to identify career opportunity zones at the optimized intersection or ‘ideal trifecta’ as I like to say of 1) what you like, 2) what you are good at, and 3) what pays the bills. You’ll notice this pulls from the classic design thinking framework: desirability, feasibility, and viability (DVF).

Part I. What are you interested in or curious about?(desirability)

Part II. What are you good at? (feasibility)

Part III. Does it pay the bills? Is it future-proof? (viability)

Part I. Identify what you are interested in / curious about

First things first: I’m giving you permission to do something scary and that is think really, really BIG about what is you might like to do. Put on your Curious George hat, and remove all career constraints, limiting beliefs, and misconceptions. I promise, in Part III of this guide, we’ll apply the practical lens of ‘Okay, but does what I like to do actually pay?’ For now, say goodbye to those constraints! Poof! Begone!

Here are some pointers for ways in to scratch the itch of ‘hmmm what do I like to do??’ Feel free to try all of these pointers or pick 1-2 that resonate most with you:

1. What do you NOT like to do? Sometimes this is easier to answer than what you do like. Knowing the industries you dislike (e.g., for me, financial services and insurance) and the day-to-day responsibilities you dread (e.g., for me, financial modeling and project management) is crucial. Write down what you don’t like in your journal or Notes app sheet for clarity.
2. Have candid curiosity career conversations (the 4xC). Start coffee chatting with people who are doing cool things that spark your curiosity. (You can discover people to chat with and find recommended questions on oyster). I highly recommend keeping these interactions as frictionless as possible for the other person. Remember: this is not a time to solicit a referral or a formal job interview. Instead, treat this as what it is: a 20-30 minute, informal, low-stakes conversation where your only objective should be to learn about the other person, their unique career trajectory, and the lessons they have learned along the way. I like to call them ‘candid curiosity conversations’ and have been doing them consistently for the past five years. Even when I absolutely loved my job at frog Design, I was still having coffee chats with people working in niche spaces that caught my interest. It was through coffee chatting I realized I wanted technology and media to be the orbit I specialized in.
3. Consume content with intent. Read, listen to podcasts, and watch content within your areas of interest. When I realized I had a passion for the media/entertainment industry, I started listening to the podcast The Town with Matt Belloni. This podcast actually came recommended to me from a woman in the media space that I spoke to in a coffee chat. I still listen to this podcast each week on full blast like it’s candy. What publications, books, or shows feel like candy to you? If you haven’t discovered them yet, wander around a bookstore and see what titles grab you. Check the arts, science, and travel sections. Use the “Discover” page on Apple Podcasts to browse new topics.
4. What challenges drive you nuts in this world? Much like they say envy can be an indicator of something you want, so too can anger. In my case, the DMV, is a great example: The sheer lack of speed in how it operates has always infuriated me. I can’t help but imagine, What if there were AI-powered, self-service kiosks? The same goes for doctor’s offices: What if I didn’t have to re-upload my information every single time I came for a visit? These are government and healthcare problems, and I was brainstorming solutions in the emerging tech space, so I were to really narrow some this career space opportunity area it would be: Industry (e.g. healthcare) → Organization Type (e.g., likely a startup more so than a large slow moving bureaucratic entity) → Roles (e.g. innovation and technology). Pay attention to the world around you and the issues that make you angry. That anger is a clear indicator that you care, and odds are, there is a career path in that space. To bring it back to my own career journey: oyster is a prime example of following the thread of what makes you angry. The one thing that has rattled me the most in this world to my core since I was 15 is that social media platforms today, even career sites like LinkedIn, fuel divisiveness, comparison, and misinformation. I wanted to as corny as it sounds “be the change you wish to see in the world.” Perhaps that’s what Gandhi meant!? Instead of stewing idly in your frustration, use it as fuel and a northstar to drive a positive impact.
5. The more things that light you up, the merrier. A lot of people like to think there is one ‘holygrail' job, but the reality is we are multifaceted human beings and thus there are multiple career spaces that might resonate with us. This is a great thing because it means (in Love Island language) that “we aren’t putting our eggs in one basket.” In college, I put my favorite organizations on a vision board: Disney, Airbnb, sweetgreen, Parsley Health, and Fahrenheit212 (an innovation consulting firm). While it may seem like a random smattering of companies, the common denominator was being passionate about innovation and companies at the forefront of innovation. I remember reading in Fast Company how the founders of sweetgreen envisioned scaling to the size of McDonald’s; that vision excited me (and still excites me!). While I ended up pursuing consulting at Fahrenheit212 because I liked that it allowed be to try out a bunch of different industries, the point remains: whether it’s video gaming, sports betting, and/or creating new ice cream flavors, it’s okay — no, it is GREAT — to have a few organizations or career spaces of interest. Don’t limit. If, it feels authentic to you, write it down. In addition to those innovation-led companies, I put winning ‘Best Screenplay’ at the Oscars, starting a VC firm, bringing Yang’s Dumplings from Shanghai to NYC, distributing nut-free delicious snacks to airplanes on my vision board, and an idea for what would later become oyster. I love looking back at these potential career stops I marked down, because I still for the most part genuinely love each idea and have it as a reference point of something I know I would like to do if ever I find myself at a career crossroads. Our careers are decades long, there will be many stops along the way, so write down any potential stop that might fascinate you.
6. Watch Disney Pixar’s Soul.

Part II. Identify what you are good at

Time for a bit of a reality check: I might love singing and dancing but I am absolutely dreadful at it. Not all of us can be Hannah Montana. That said, you will likely find that your career interest areas align with your natural strengths. Here is how to identify what it is you’re good at:

1. Look at your academic history. Think back to the classes or activities you excelled in. There has been a recurring theme for me: I’ve always loved and been relatively good at English, history, and the arts. While not directly related to business and technology, I would argue English, history and the arts is certainly adjacent and involves similar skill sets: writing, analysis, and creative thinking. No surprise, I ending up becoming an Innovation Strategist. So, ask yourself: What were the classes you actually looked forward to each week in school?
2. What tasks make you lose track of time? I love building slides. No really. Even when I was in middle school, I would put together Word Art designed presentations (dorky, I know). It sounds ridiculously boring, but it’s tied to my love of storytelling, which I’ve loved doing since I was a kid — taking complex topics and turning them into simple, relatable insights. Think back to moments in a job or task where you were in a state of flow. You were likely doing something you were both good at and genuinely interested in.
3. Check your cookie jar. I highly recommend keeping a running file of the kudos and praise you receive from teachers, peers, and managers. I’ve been tracking this since I started my career. Not only is it a confidence boost, but it’s a great reflection of, “Okay, I really am good at XYZ skill.”

Part III. Identify if it actually pays the bills. Also, is it future-proof?

Many people pursue careers in consulting and finance for the promise of a good salary, but the reality is that many of those roles, particularly at the entry level, are enduring constant rounds of layoffs and restructuring in today’s world of work. My salary as a corporate consultant hardly changed over the course of 5 years because of so much industry and organization turmoil. So, in addition to really validating if the job you think pays the bills actually pays the bills, it is important to ask: 'Is this role future-proof?' Example: Chandler Bing’s job might have paid well, but it certainly didn’t bring him much joy, and that specific type of work he did is currently seeing massive shifts and evolution due to automation.

Another example: Many research and analysis roles are seeing a transformation right now. So, even if you love to research or UX/UI (like I do), be aware that you will likely need to lean into cutting-edge AI tools to maintain your value. Much like the Internet and Microsoft Office were new tools that impacted the evolution of key roles, so too is AI. This is not about being a proponent of AI, but it is about recognizing that A.I. is happening and here to stay (especially in such a capitalist driven country that is decades slow to any kind of regulation), so you’d be remised to not do some homework and see not only which roles and industries are being affected, but how they are being affected because pretty much every role and industry is being affected (albeit some more than others).

Here are some pointers for the viability check:

1. Challenge your misconceptions about which jobs pay well and their job requirements. Hot take: I predict we are going to see a massive shift away from the traditional path of four-year universities and entry-level finance or consulting roles, and toward careers for mechanics, technicians, and artisans—all of which are heavily in demand (and for years to come), do not require a college degree, and, in some specializations, pay as well as an investment banker. Regarding job requirements: if you are considering an MBA or a graduate degree, I urge you to seriously weigh the ROI before committing. Consider these points:
   1. It may not be required for the role you want to pursue. Talk to people in the field to get their advice
   2. It is likely becoming even less essential with the onset of AI and the rise of more accessible upskilling programs
   3. Experience is often the most valuable credential. If more schooling isn’t mandatory, ask yourself: how can I gain practical experience in the field, rather than paying six figures for another degree?
2. Schedule coffee chats with people currently in the roles you’re interested in (you can find them on oyster). There is no better way to dismantle misconceptions about which jobs are high-paying and future-proof than by speaking directly to someone in the field and role at your career stage. This is how you de-risk a pivot, and get to dip your toes in before taking the leap. Talk to someone who is already there. Ask them what they love, what they dislike, their compensation, their work-life balance, and how the role has evolved, specifically, how technology has or hasn’t changed their day-to-day. If they mention constant layoffs and high turnover, treat that as a red flag.
3. Do your secondary research. Coffee chats are primary research, but don’t neglect secondary research online regarding salary benchmarks and delving deep into how your industry or organization of interest is faring in regards to market and technological shifts. Read annual reports and/or industry papers. Not every team is treated equally in an organization too, are there some teams faring better with economic tailwinds?
4. Can it start as a side venture? Sometimes the things we love, don’t pay the bills right away. If your side venture is the main thing you are passionate about and good at but doesn’t yet pay the bills, then I would recommend strategically picking a ‘day job’ that provides the flexibility to explore your side venture. After moving on from consulting, I opted for strategy freelancing rather than a more high-paying full-time media role because I knew I wouldn’t have the time or bandwidth to continue actively contributing to my passion projects of oyster and screenwriting if I took it. That full-time media role would have sucked up 150% of my time, and I didn’t want to delay the oyster and screenwriting dreams I have any longer. If the strategy freelancing gig hadn’t panned out, I would have looked for another part-time job or 9-5 that I cared less about so I would still have the emotional headspace to do oyster and screenwriting.
5. Geolocation audit: Can you move? Let’s be real, taking a more passion-aligned role that pays less might not cover your expenses in NYC (this was me). Is it possible to pursue a role you love in a more affordable city? Cutting down on rent, clothing, beauty, or dining out can provide the financial breathing room to accept a role that pays less but offers more personal fulfillment. Figure out what you value most right now in a career – passion, work-life balance, or compensation – and prioritize accordingly. Post-COVID, one of the silver linings has been the rise of remote working and the digital nomad life. Not to mention, the world is more interconnected than ever before with globalization. There are literally millions of organizations out there in the world and odds are someone out there is likely doing what you want to be doing – the hard part until now with oyster, has just been finding them. Now, you can.

Parting words

Give yourself grace. The only guarantee in life is that you will change, so it’s ridiculous to think you’ll be in the same role for 30 years unless the organization can evolve with you much like a life partner. We aren’t static human beings and therefore our careers aren’t either. When you’re looking to start a family, a fast-paced startup might not be as conducive to your life as it was in your 20s. Or perhaps you join the healthcare industry and discover it’s so slow-moving that it leaves a sour taste in your mouth. As my mom always said, “We don’t wear cement shoes.” It is always okay to give it your best shot and then pivot if it’s not working. Crafting a career at the intersection of what you like, what you are good at, and what pays the bills is a lifelong journey. oyster is here to support you along that journey.

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