Cold Start Careers - An Overview
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Cold Start Careers - An Overview

Worth opening this by saying a lot of these thoughts stem from a sense of fear and helplessness about my own destiny when embarking on job hunts and career navigation, especially as someone whose background has been founder → startup employee for the first 7 years of his career.

At the same time, I know that this is not a unique feeling, and that everyone everywhere does feel anxiety and uncertainty when it comes to finding work. This gives me some comfort, but also motivation to speak my mind in hopes that it could help others feeling the same way.

This article aims to unpack the uncertainties, anxieties, and frustrations of the job hunt process, and propose a new high-effort way of applying to jobs that should increase the success rate of you finding jobs that you want.

Do any of these feel familiar to you?

  • You’re looking for your next job - or maybe you’ve just graduated, or maybe you’ve been working for 15 years and you’ve been out of a job for a year. You brush up your resume, and you contemplate writing a cover letter but decide not to, and you apply to as many jobs as you can.
  • Some jobs are a single click “quick apply”, and others require you to wrangle some Workday or another god-awful ATS form, where you upload a resume but still write down the same details that you’ve already added.
  • You don’t hear back from anyone, and you wonder if you’re not worth anything in this job market. And it’s especially bad because you don’t quite know what you did wrong.
  • You hear about your friends getting recruiter calls or a whole bunch of interviews from big companies, and they’re already working for big companies!
  • Others give you generic advice about how your resume isn’t adhering close enough to the STAR method or that the format isn’t close enough to what is ideal for recruiters, or you’re just not showing how ✨impactful✨ you are at work!!!
  • You contemplate getting a bunch of certifications to put on the resume and LinkedIn, and you toy around with writing a bunch of cover letters for jobs you are really excited about. You actually get them done, and you mass apply and send out those meticulously written cover letters. Still nothing. Then do all those courses for what?
  • You contemplate going for some networking event, where some founders or prominent folks are talking. Maybe you’ll go talk to some of them. But what the heck do you say? “Hi dude great talk gimme a job - I’m gonna go hungry otherwise”?
  • Some friends suggest “oh go get referrals they’re sure to work!”, and so you do. You connect with some folk on LinkedIn, with a note saying “hey I saw you’re working in this company, would you be ok to refer me in?”. No one replies, you feel sad.
  • Maybe you get an interview or two, but the interviewers don’t seem particularly impressed by what you have to say or the things you’ve done. They don’t care about your extracurriculars, or the fact that you led a whole social media campaign, or that you’ve created a python app based off a tutorial you saw online, or that you managed a pretty significant project in your company. I’ve done the work, why don’t they want me!!!
  • Maybe you get some offers, but you’re expecting me to say yes to a $3.5k software engineering job?? I have a whole family to feed and you’re giving me $3k for a digital marketing manager job?? But am I being picky if I say no to these opportunities?
  • Some other friends tell me that the job posting is just there because companies want to justify that there are “no suitable candidates”?? How like that???
  • Other friends say that the market is just bad, and it’s not your fault that you’re not getting enough callbacks. Doesn’t help the current situation though…
  • You start to lose hope, and go for a trip to chill out for a bit. Then you look at your bank account and freak out even more. Or your significant other applies pressure on your extended unemployment after that layoff, or you feel an even larger sense of dread every time to wake up in the morning to go to the job you now view as a dead-end.

Rough, right? And it’s even more frustrating sometimes because a lot of conventional wisdom is not necessarily wrong, AND it has worked for people here and there! Things like “network more”, or “change up your CV”.

Ok now you’re just making me feel crappy - where are you going with this?

Even if more conventional advice works here and there, there’s an unshakable feeling within me that the process of hunting for jobs is pretty broken and extremely difficult to navigate effectively.

As organizations get larger, more and more arbitrary obstacles come in the way of you even being considered as a Human Being©️ that could have Value To Bring To The Company™️. Forms, AI CV-filtering systems, robo-video-interviewers, psychometric and IQ tests, and 20,000,000,000,000,000,000,000,000,000,000,000 interviews (more than the GDP of the world). Meanwhile, smaller organizations have a general tendency to ask for the sky and pay a looooot less, with fewer opportunities for growth in pay and skills, and once we get into such a role, it can feel very demotivating and draining, and the feeling of being “stuck” sets in.

It’s also not straightforward how one could climb the ranks or navigate one’s way to better opportunities in such an environment - the days of finding a big good company and staying there for a lifetime has been over for a long time, layoffs are getting more and more prevalent across most sectors, the playbook of the 2010s of joining startups that you can ride along to a path of growth is getting less common with the end of the Zero Interest Rate Period (ZIRP) era, and no one really knows how the next decades would look like anyway.

SO, putting aside the uncertainty aspects of how the ✨future of work✨ would be, I pointed my attention to thinking about what are aspects that make you appear (or actually make you, I suppose) valuable. Had some fun “brainstorming” (read: cheating) with Claude, and this is what they came up with:

1. Educational Background

  • Degrees from prestigious institutions
  • Advanced degrees (MBA, PhD, etc.)
  • Academic honors and distinctions
  • Research publications
  • Study abroad experience

2. Professional Heritage

  • Experience at well-known companies
  • Previous roles at industry leaders
  • Progressive responsibility at respected organizations
  • Association with successful projects/products
  • Working under renowned industry figures

3. Network Capital

  • Alumni networks from elite schools
  • Industry association memberships
  • Professional organization leadership roles
  • Mentor relationships
  • Previous colleague connections
  • Family/social connections in the industry
  • Board positions

4. Demonstrated Expertise

  • Published work/thought leadership
  • Speaking engagements
  • Patents or innovations
  • Industry awards/recognition
  • Portfolio of successful projects
  • Measurable business impact
  • Technical certifications

5. Social & Communication Assets

  • Multiple language fluency
  • Cross-cultural experience
  • Public speaking ability
  • Leadership experience
  • Strong writing skills
  • Media training/presence
  • Executive presence

6. Market Position

  • Rare/high-demand skill combinations
  • Industry-specific knowledge
  • Regulatory expertise
  • Crisis management experience
  • Change management track record
  • International business experience

7. Digital Presence

  • Strong LinkedIn profile/following
  • Professional website/blog
  • Github contributions (for tech)
  • Digital portfolio
  • Social media influence in industry
  • Online course creation

8. Personal Brand Elements

  • TEDx or similar talks
  • Book authorship
  • Podcast appearances
  • Regular speaking engagements
  • Column/blog writing
  • Community leadership roles

9. Entrepreneurial Track Record

  • Successful startup experience
  • Business ownership
  • Patent development
  • Product launches
  • Fundraising success
  • Exit experience

10. Specialized Training

  • Military background
  • Government clearances
  • Professional certifications
  • Specialized software expertise
  • Industry-specific methodologies
  • Risk management experience

There’s a whole bunch of things that are harder to attain (e.g. specialized training, network capital, educational backgrounds, or connected relatives that can get you that job at that big bank or organization that will really give you an edge), though it could be a valid strategy to pour in a whole bunch of effort to try to attain them.

  • Someone who did not do very well academically at the start may double down in getting a good degree in a private university, and use that to get a master’s that could unlock jobs.
  • Someone who is extremely keen on a specific area of research could grind their way to working under the tutelage of an extremely renowned professor in that field.
  • Someone who has the means to take risk could dive into an entrepreneurial venture, and should that fail, pivot into something that values the experience they’ve gained (or if they succeed, get acquired into a company they align with, or just straight up make boat-loads of money).
  • Someone could really grind their way to 1st class honours with stellar leadership credentials, a whole bunch of shiny internships and case competitions under their belt and intensively apply their way into MBB.
  • Someone could go from organization to organization until they find a leader that is extremely keen on championing their climb within the organization they are a part of.

All very valid paths, and I am certain there are many others. I’m not here to claim that there is one correct path, nor am I saying that it is something that we have complete control over.

However, I AM here to paint an approach that is accessible, high effort, and that gets stronger and more compelling over time.

More specifically:

  • Take an almost unreasonable amount of time to synthesize and document how much Demonstrated Expertise you have accrued over the course of your career, projects, interactions with people and knowledge
  • Curate and launch a Digital Presence that people can easily navigate and will actually care about
  • Building Network Capital from scratch, by exposing them to your Demonstrated Expertise through the Digital Presence you have curated, or ad-hoc documents that you create just for them.
  • Repeat the process & use the building blocks you create to better strengthen your Digital Presence, continue refining and expanding your Demonstrated Expertise, and accrue Network Capital built on a foundation of expertise, inquisitiveness, work ethic, and grit.

I recognize that there are situations where holding your cards close to your chest is the correct play. I generally don’t spend much thought thinking about those situations at this stage of my life, but it’s worth discussion.

Before going deeper into the approach, I wanna further justify the need for such an approach by describing what I call the Cold Start Career Problem.

The Cold Start (Career) Problem

The concept of the Cold Start Problem was popularized by a venture capitalist named Andrew Chen, who posits that launching and scaling new (digital) products and services remain difficult, and that founders generally need to overcome the aforementioned Cold Start problem before they can even dream of seeing success.

The Cold Start Problem constitutes 3 main components:

  • The Chicken-and-Egg Dilemma: At its core, the Cold Start Problem presents a paradox where a product needs users to be valuable, but users will only join if the product is already valuable. This creates a challenging situation for new products trying to establish themselves in the market.
  • Lack of User Data: For products that rely on user data to provide personalized experiences or recommendations, the absence of initial user information can hinder their ability to deliver value from the start
  • Critical Mass: Networked products often require a certain number of users to reach a "tipping point" where the product becomes truly useful and can sustain growth. Achieving this critical mass is a key challenge in overcoming the Cold Start Problem

Conversely, the Cold Start Career Problem can generally be summarized as:

  • The Career Catch-22: You need experience to get a good job, but you need a job to get experience. This is especially evident in the article's description of job seekers struggling to prove their value despite having done relevant work (like creating Python apps or managing social media campaigns) that employers don't seem to value without formal professional experience.
  • Lack of Employer-Side Intelligence: Job seekers don't have clear visibility into what employers truly value or why they're being rejected. The article mentions how people don't know what they did wrong in applications, get generic advice about STAR methods and formatting, and face opaque obstacles like AI CV-filtering systems and arbitrary application processes. This information asymmetry makes it difficult to improve or adapt effectively.
  • Critical Career Capital Mass: Just as products need a critical mass of users, careers need a certain accumulation of the right credentials, experiences, and networks to become self-sustaining. The article's extensive list of advantages (educational background, professional heritage, network capital, etc.) suggests that career success often requires building up multiple reinforcing elements that create momentum. Without this critical mass of career capital, job seekers struggle to break through initial barriers.

Each set of 3 components can be sorta mapped to one another:

Cold Start Problem
Cold Start Career Problem
Chicken-and-Egg Dilemma
Career Catch-22
Lack of User Data
Lack of Employer-Side Intelligence and Attention
Critical Mass
Critical Career Capital Mass

Going into how to overcome the Cold Start Problem:

  • Focus on Initial Value: Creating a high-quality product that provides immediate value to early adopters is crucial. This often involves identifying a niche market and tailoring the product to meet their specific needs.
  • Start with an “Atomic Network”: Chen advocates for starting with an "atomic network" - the smallest possible group that can derive value from the product. This could be as small as a group of colleagues or as large as a community of residents.
  • Leverage Network Effects: As the product gains users, it should be designed to become more valuable with each new user, creating a positive feedback loop that encourages further growth.
  • Iterative Growth: Once the initial network has been established and nurtured, the process can be repeated to expand into new user segments or markets.

Conversely for overcoming Cold Start Career Problems:

  • Focus on specifics: Instead of broad applications, deeply research and target specific companies/roles where you can clearly demonstrate value. Customize your approach to show exactly how your skills match their needs.
  • Build an "Atomic Capability Demo": Create tangible, demonstrable pieces of work that shows your capabilities in action - whether it's a bunch of projects, analyses, or solutions to different industry problems. It is important to start small so that it actually exists in the world.
  • Get Things In Front of the Network: Actively share your work and insights with relevant professional communities. Present at meetups, contribute to discussions, write detailed case studies - make your expertise visible to those who matter.
  • Building Blocks to the Sky: Each demonstration of capability should build on the last, creating an increasingly compelling narrative of your expertise and impact. Start small but keep stacking achievements.

Doing all this should build up both demonstrable career capital and meaningful professional relationships - the two key ingredients that help overcome the initial "cold start" barriers in any career transition.

Cold Start Problem
Cold Start Career Problem
Focus on Initial Value
Focus on Specifics
Start with an “Atomic Network”
Build an “Atomic Capability Demo”
Leverage Network Effects
Get Things In Front of the Network
Iterative Growth
Building Blocks to the Sky

Thanks for the fancy categorizations - so what do I do??

I suppose a good place to start is to review how the process is usually handled, and from there, I’ll propose a course of action that aligns with the principles outlined in the previous sections.

Usually, job applications generally goes like what was described in the introduction, but in short:

  • Draft a CV, maybe a cover letter
  • Apply to hundreds of companies
  • Hopefully interview for a fraction of those companies, multiple times
  • Hopefully get one or more offers
  • Hopefully secure an offer that you want

I made a handy-dandy graph to outline how things are likely to go with this approach:

image

If you’re leveraging on your network and you put in a bit more time into CVs and cover letters, it usually goes more like this:

  • Draft a master cover letter and CV, and have multiple CVs for different role variations that you apply for
  • Reach out to people you know or people you know who know people in companies you want to apply for, and request for referrals very nicely. At the same time, still apply to hundreds of companies cold
  • Secure more interviews because of the referrals, and interview a bunch of times again
  • Hopefully get one or more offers
  • Hopefully secure an offer that you want

Because there’s additional agency being exercised, the amount of reliance on hope is reduced! It does require more energy to tailor your CV and cover letter, but if it leads to better outcomes, why not!

But part of why the problem is described as a Cold Start in the first place is that there’s still a pretty big degree of luck involved in securing the opportunities, or even getting people to say yes to referring you. Sure, the more you do it, the higher the chances someone might say yes, but you’re still facing a slowly but surely depleting energy pool while not necessarily building leverage quickly enough. Or as this handy-dandy graph shows:

image

My proposal would be to:

Synthesize, Document, and Communicate Demonstrated Expertise

The atomic unit of communicating Demonstrated Expertise is the Project. Regardless of whether you’re a (prospective) software engineer, VC analyst, interaction designer, product manager, strategy associate, business developer, marketing specialist, operations manager, HR business partner, financial controller, or WHATEVER occupation, it can never hurt to demonstrate a keen understanding of your job by creating a Thing™️ that shows you understand.

Broadly speaking, projects could come in the following forms:

  • Take specific aspects of the work that you do that would normally take 1 line on your CV, and elaborate on it
  • Creating an overview document of your understanding of the role at the level you’re currently at
  • Creating an overview document of the industry you currently, used to, or want to inhabit, and hint at the unique insights you have about it
  • Document the process and success metrics and/or skills demonstrated while:
  • Analyze something, draw conclusions, suggest recommendations, put it in a word document or slides
  • Create a blog, and treat each blog post as an individual project that demonstrates your understanding and perspectives about a Thing™️
  • Put together a strategy document or action plan for a process improvement in your current company, your ideal company, or a hypothetical company

Maintain a Clear and Easily Accessible Digital Presence

Make a website, make it yours, treat it like a representation of who you are AND who you want to be that happens to inhabit the 🌐internet🌐.

  • Your main + about me page should be optimized around the sort of role you’re gunning for.
  • Each project should ideally occupy its own page.
  • Maintaining an “interests” page also allows you to show the more ✨human✨ side of you!
  • Some examples I found of product manager websites.

(I’m on the hunt for other portfolio compilations - may compile more on my own! If you have one and would love to be on a list, message me).

Seed Then Snowball your Network Capital

You’ve done the projects, you’ve put it online - now it’s a matter of putting it in front of people!

Some things to consider here:

  • Having projects under your belt allows you to bring it up briefly in conversation, get the person’s number/LinkedIn/email, and send it as a follow-up message as opposed to sending your entire CV in a completely unsubtle manner that screams “GIVE ME JOB PLEASE”.
  • Having a well organized website also allows different hiring managers/interviewers to have a visual aid to the points you may include on your CV, and makes for a more robust conversation during interviews. It also allows you to send better “thank you for interviewing me” emails.
  • Even if you’re embarrassed by the initial state of your website, it gives people the ability to provide feedback that you can take in and act upon, which will then improve the quality of your Demonstrated Expertise and Digital Presence.

(Each of these points deserves a post of its own, so to get this article over the finish line, I’m satisfied with this level of elaboration for now 🙃)

This allows us to actualize the aspects that we outlined previously in How To Overcome Career Cold Start Problems:

  • Focus on Specifics: Taking a project-based approach keeps things contained and manageable, and gives you the opportunity to demonstrate a specific Demonstrated Expertise in a way where you’ll actually finish the thing, put it out there, and move on to the next thing.
  • Build an “Atomic Capability Demo”: having your Digital Presence start small allows you to overcome the initial friction of putting yourself out there, and it gives you the ability to show at least one piece of Demonstrated Expertise. At some point, you can replace older projects with newer ones.
  • Get Things In Front of the Network: Having a Digital Presence that showcases your Demonstrated Expertise allows you to start building Network Capital with a “show, don’t tell” approach. Saves you energy by not needing to talk so much ;)
  • Building Blocks to the Sky: Your Demonstrated Expertise will only improve over time, and your Digital Presence will only get more robust over time. At some point, you’ll be shocked at how much progress you’ve made by watering your plants bit by bit consistently. Eventually, your Network Capital will snowball in ways you could have never imagined.

If all goes well, the handy-dandy graph is likely to look like this:

Yes, it is a tad optimistic. But indulge me for a bit ya
Yes, it is a tad optimistic. But indulge me for a bit ya

If these thoughts look familiar, it could be because it’s heavily influenced by swyx’s perspectives on:

Who is this for? Everyone? Specific Industries?

I initially thought that this approach was more suited for folks looking to get into tech, where the possibility of a project-based approach was more viable and where it was much more competitive because of the lower barrier to entry of actually picking up these skills compared to, say, hard engineering companies, financial institutions, management consulting (skilled?), and other fields where hard industry knowledge is a must.

But I’m actually very convinced that this is something that would very likely become the norm for all jobs going into the future.

  • Jobs are either going to be commoditized, automated, or require the individual worker to deal with more complexity and pick up new things regardless of industry. Being conscious, deliberate, and communicative about how you’re someone who can do more with less OR handle more complexity as an individual worker will make you more valuable regardless of industry.
  • It is possible to pick up enough of the basics of any industry with enough thought, enough learning, enough synthesizing, and enough creativity in how you select and do projects.
  • No matter your function - be it in HR or sales or BD or strategy or operations or whatever, it will never hurt to put your thoughts down and be reflective about how you do your job.
    • The ROI would be different for each occupation, but we can (and will!) unpack that on a case-by-case basis.
  • It’s also the case that to progress in tech, you also need hard industry knowledge anyway!

Closing - what else am I thinking about?

As with many things in life, I have a bad habit of trying to find the answer - like if I just thought about a Thing™️ long enough, I’d be able to deduce how to Solve It Completely©️. What an unhealthy way to approach life Evidently, nothing in life works like that. But the wonderful thing about trying to answer a question is that some answers are spawned, and more interesting questions appear as well!

SO, specific to Cold Start Careers, I am looking into figuring out:

  • What are some generalizable techniques one can employ in the interview process that allows you to really bring out your Demonstrated Expertise
  • How exactly do you think about scoping, working on, completing, and showcasing projects relevant to a bunch of different domains, industries, and functions (tech and otherwise)
  • How this approach is compatible at different career stages
  • How does one manage energy, motivation, and emotions through doing this High Effort Thing™️

But beyond that, I’ve got a lot of other thoughts that I would like to deep dive into! Here’s a sneak peek (and in place of my thoughts, I’ve put a bunch of links that talk about it).

“Those who are more appealing to co-workers and employers tend to be the ones who make life easier for others around them”

What to spend time working on?

Becoming excellent to do impactful work?

How do we figure out how we’re ✨special✨ and ✨valuable✨

The future of work arrangements - navigating the messy middle and the end of traditional jobs?

Why You Should Build a “Career Portfolio” (Not a “Career Path”)

Up until this point, we have lacked the language necessary to design our careers in ways that veer from the traditional script. But now there is hope. A new vocabulary is emerging. At the heart of it is a shift from pursuing a “career path” to creating your “career portfolio.” Whereas a career path tends to be a singular pursuit (climb the ladder in one direction and focus on what is straight ahead), a career portfolio is a never-ending source of discovery and fulfillment. It represents your vast and diverse professional journey, including the various twists and turns, whether made by choice or by circumstance. While your portfolio can include traditional paid jobs, don’t limit it to that. Think bigger. Your portfolio is created by you, rather than determined for you by someone else (like a bunch of hiring managers).  It reflects your professional identity and potential. It includes your unique combination of skills, experiences, and talents that can be mixed, matched, and blended in different ways. In a world of uncertainty, talent that can expand their thinking beyond boxes, silos, or sectors will be in demand. Those who make an effort to build a career portfolio now will be more prepared to pitch themselves for (and even create) new opportunities, as they will be well-practiced at making creative connections between their various skills and the skills required of the jobs they most wish to pursue.

Why You Should Build a “Career Portfolio” (Not a “Career Path”)

Combating ageism in job searches, and the plight of mid-career switchers

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