The Antidote to "I am feeling stuck in my career"
Mental models and planning guidelines to get unstuck on the career path
"What should I do next? 🤔" — a common conundrum. I have faced it; many others have, and perhaps you too. Not everyone, of course. Two types of people escape this ambiguity: the sorted few who have it all figured out and the clueless, who don't know or care. The rest of us aren't so lucky. We must deal with this uncertainty eventually.
The antidote, I propose, is a two-part solution:
A mental model. Growth paths, their defining characteristics, and the cost of switching paths.
Actions to take. How do you make tangible progress toward your path? How do you discover your path?
The Three Paths
A bigger and better job, a.k.a. climbing the corporate ladder 📈
Free agent, freelancer, or the more sophisticated — consultant👨🏼💼
Equity owner of a product or services business 💰
Let's look at each.
1. Climbing the Corporate Ladder 📈
This is the most common, the most accessible, and the most understood path. It's exactly what you imagine. You keep taking up bigger and better roles at bigger and better companies. For most people, this path terminates in roles such as "SVP at Apple," "Distinguished Engineer at Google," or equivalent in other world-leading companies.
To Walk The Path
This path rewards demonstrable skills and pedigree. Data structures and algorithms are a standard proxy for skills in software engineering. Pedigree manifests in various forms, but the two most common forms are the college/university you graduated from and your past employer. If you have worked at Netflix for a few years, switching to Google or Meta is more straightforward than others. Quite understandable.
Upward mobility is achieved through promotions and job changes. Politics, diplomacy, and people skills are the other half of rewarding skills—especially climbing. Promotion cycles at BigTech are notorious for being riddled with biases, pompousness, and showmanship. Not always, of course. Never always. But enough to factor it into your plans.
Rewards
Ladders offer mid-to-high financial rewards. At the top of the ladder, you're looking at a $XM/yr to $XXM/yr compensation. It can go even higher in outlier cases. All higher rewards are rooted in equity. Strong stability is also on the cards. Fortune500 type employers tend to be more stable. However, the layoff waves from 2022 to 2024 would make us question the stability, and the work/life balance has always been employer-dependent. A tyrant manager is as typical as a coasting employee. YMMV.
A certain prestige is also associated with the corporate ladder by brand association. If you're an engineer at Mercedes-Benz, you will enjoy some adulation. Every kid on the corner can identify the three-pointed star. You get lifelong brag rights if you were on the GitHub team in their first few years.
Can You Change The Path?
A striking feature of the corporate ladder path is you get to change to other paths quite easily. If you're a Staff Engg at Meta, the chances of you raising VC capital are always higher than someone who has only worked at startups. It gives you network, access, and exposure to change your path to freelancer or equity owner with equal ease. Finding new clients or selling your services to strangers is easier with a powerful employer on your resume. Note that jumping back is more challenging, as we will see later.
What upward mobility looks like
Senior Software Engineer → Staff → Principal
EM → Director of Engineering → VP
Scaled Startup → Multi-National Corporate → BigTech
EM in BigTech → VP in Scaled Startup
Multi-National Corporate → Early Employee at a marquee startups
Getting paid as per local markets to joining a global remote company
And so on.
The only common thread in all corporate ladders is the presence of a manager—somebody you report to. This leads us to the next path.
2. Free Agent or Consultant 👨🏼💼
Look, ma, no boss!
- No consultant ever.
Replace a manager with a client, a regular income with variable income, and an employer brand with freedom — you get a consulting career. It is tempting to objectively compare the free agent path vs the corporate ladder path, but it ultimately comes down to personality and preference. Some people prefer the ladder, and a few choose the freelancer approach. Being a free agent comes with undeniable freedom. It's in the name. But it also suffers from the cold start problem.
To Walk The Path
You're rewarded for reputation, performance, and referrals. Referrals and reputation get you leads, and a high performance keeps the engine running. When they said, "I know a guy who knows a guy," they meant consultants. A consultant who repeatedly does only one thing for all their clients gets paid handsomely for that one thing. I recently connected with a highly successful consultant for just one job: Enterprise Integrations. That is all they do. And they take home a compensation equivalent to a Principal Engineer at BigTech.
Consulting starts with slow periods when you are new to lead generation and client service. But it's a compounding process if you're good at your job. Savvy sales and marketing skills can speed things up, but fundamentally, consulting is about client service. A happy client builds your reputation and gains you leads. After you attain critical mass, you see rapid growth, which eventually tapers into stability.
The two ways to get paid
Time and Materials — A battle-tested strategy where you charge for your time proportionate to your demonstrable expertise and value. Everyone understands it, and it's an easy sell. The downside? It's capped. There's only so much you can charge.
Value-based or Outcome-based pricing — Marketing and Sales executives have been doing it forever. Think of sales commission. You get paid a proportion of the revenue you bring to the business. In recent years, Product and Tech consultants have also started outcomes-based pricing. You offer an agreeable, tangible value, such as improving iteration speed for a product development team, fixing scaling issues, etc. You get paid proportionally to the outcomes. It's not a straight cut like a sales commission; it's more complex. But doable, especially for senior executives. This type of billing offers uncapped high rewards but is less prevalent and a hard sell.
How much do you get paid?
Solo consulting comes with some caps on how much you can make. Let's take two cases on the higher end of the spectrum:
Nikita Bier, a famous product person with a niche speciality for building viral apps, charges $10000/hr for consultation. There aren't enough companies worldwide to keep him fully booked, but even if he gets 200 billable hours in a year out of 2000, he's looking at pocketing $2M. This might be pennies for Nikita, but certainly not for everyone.
A well-known programmer in my network (who requested anonymity) charges $2000 per hour for their services. Given their skill and reputation, this is such a bargain that they are entirely booked for the year. They choose to work 1000 to 1200 hours annually. By simple calculations, their net annual income is $2000/hr multiplied by 1200 hrs/yr, equaling $2.4 million/yr.
Consider this a cap for your personal $ rate. This is as high as you go. In any case, A cash-rich life is an eventuality for freelancers, unlike startup employees.
What about changing the path?
Climbing the corporate ladder is a challenge for freelancers. For various reasons. You will most certainly get down-leveled and will have to earn your way back up. You're used to the freedom, and the compliance-driven nature of employment can set you back. You may need more proof of work than just a client list. And so on. But it can be done. You will find many who routinely switch back and forth, too.
However, the natural progression for free agents is into equity owners of services firms. At some point, you have enough leads to delegate work and enough talented people around you to delegate the work to.
This brings us to path number three.
3. Equity Owner of a Product or Services Business
The most admired (or hated, depending on who you ask) and the least traversed path of all three. Least traversed because it's undeniably challenging to build a profitable business. Success rates are low, but the rewards are uncapped for those who succeed. Take the Forbes Richest 100, and you'll see only equity owners. If Bill Gates had not diversified out of his MSFT 0.00%↑ stock, he would have been worth $1 trillion today. We’re not the judges on whether that is good or bad, but for pure numerical comparison, the wealthiest person today is somewhere close to $200 billion.
This path rewards two skills above all
The ability to respond to markets
The ability to hire suitable talent
Easier said than done, of course. You should pick this path if you have a burning ambition to solve a particular problem and understand the market around that problem. A chosen few, like Steve Jobs, could generate demand, create markets at will, and attract the world’s top talent. We are not them. But it’s not all or nothing — you can always start upskilling in these two abilities, team up with those who do, consult coaches, and so on.
Whether products or services, no successful business can exist without adequately serving the market. Being the equity owner of a services business is an equally viable path. It’s cash-rich, comes with freedom, and has many positives of the free-agent path we discussed earlier. However, there is resentment and hesitation towards the services business in the tech community. For whatever reasons. But it’s unfounded and shortsighted. Completely ignorable. Who knows, you might create another ThoughtWorks™ or Pivotal™.
Switching Careers is easy enough for founders.
Being a founder makes it easier to switch paths, should you wish. Countless examples exist of people moving to BigTech, other corporates, or marquee startups.
Moving from one business to another is natural, too. If you can respond to the market once, you can react twice. Serial entrepreneurship is a thing.
Actions? What can you do to progress?
No matter where you stand and which way you lean, there are 4 types of actions you can take to make tangible improvements.
1. Engage in Meaningful Work (Build Skills)
The most important of them all. You must engage in meaningful work. This doesn't have to be at your employer. It works out the best if it is, but it needn't be. Fundamentally, to build skills, you must do what you want to be skilled at. Let’s accept that there is no substitute. Sharing some ideas to pursue:
Putting more effort at work / producing better outcomes
Substantial Open Source work, such as core teams of popular projects, maintaining libraries, pruning and triaging work (thankless, I know)
Big long-term side projects. Something you keep coming back to, refining, and improving. These are great conversation builders. You will need that conversational skill when networking. More on this below.
Lots of short-term side projects.
MOOCs from top universities
Classic literature, reading research papers
I want to reiterate the “meaningful” pursuit of action here — only watching videos and reading blog posts does not count (ironic! 😄). Work at the edge of your ability and see exponential rewards. It’s a superlinear activity. Pursuing meaningful work exposes you to newer things, generating further interest that produces more work, and so on…
2. Build a Public Presence (Reputation and Portfolio)
Give talks
Write blog posts
Create videos
Engage in online conversation
The idea is to have a say and be articulate about it
When someone looks you up as a potential employee, client, or customer, they should like what they see. And trust me, look you up, they will. The beauty of public work is that it's also a compounding activity. The golden rule of compounding is when your outcomes produce more outcomes. You don't need to go viral. Consistently produce work, and the consumers of your work will bring more consumers. At some point, you will break through.
3. Networking
Seek and attend meetups
Give talks at these meetups
Attend conferences
Speak at these conferences
Invest in attending international conferences. Yes, you read it right. If you can visit Singapore for a vacation, you can visit Singapore for a conference. Even if you don’t usually take international vacations, take conference vacations. The RoI is stupidly large.
Join online communities on Slack, Discord, etc.
Consider the network effect:
The main problem? Cold start. 🥶 Quite often, meetups have too few members or are too dull. 🥱 And your circle doesn't grow. The promised huge RoI isn't visible. But as with everything else, perseverance pays. As a bonus, if you learn to follow up with people (e.g., by using a calendar or CRM), you will build a network much faster than without. Following up is a proper 10x activity.
4. Take Breaks/Sabbaticals
A periodic detox, specifically from work stress and online presence, is a biological necessity. Modern, online-driven work life is an assault on the senses, and you need shelter. Sabbaticals are that shelter. Taking regular breaks adds a dimension to one's personality outside of work.
All the actions and skills are coupled together. They reinforce each other. Consider this not-so-scientific lattice of the concepts we have discussed so far:
We will explore meaningful work, online presence, and networking in upcoming posts.
Putting it all together 🧘🏼♂️
Figure out which path you are on and which path you want to be on
Take action; make progress. If you’re unsure, actions will lead you to clarity
Evaluate your physical, emotional, intellectual, and financial ability to survive and thrive on each path.
Remember that it's not all or nothing. Spectrum thinking wins.
Very relevant and true, Swanand!