The Best Books for Building a Startup Career

When I landed my first startup job, I felt like I knew nothing. Actually, some days I felt like I knew less than nothing.

I was nineteen years old, and my previous working experience consisted of tutoring homeschooled kids and picking apples for a living. I had no idea what a quarter was, let alone a KPI. I was excited and I was hungry and I had no clue what I was doing.

I realized (much later) that it wasn’t just me. One of the most frustrating things when you’re starting your career is all the stuff you don’t know. You’re young, and you’re excited, and you have all the time in the world — all advantages — but there are some pretty big disadvantages that come with the territory. The biggest two are a lack of experience and a lack of knowledge. The latter, in part, is a symptom of the former.

When you don’t have a lot of knowledge yet, one of the best ways you can compensate for it is by reading.

Here’s the thing — to be an effective player in the startup world, there’s a lot you have to be good at. Some of the most important:

  • understanding how startups work in the first place (pretty obvious, but as I quickly discovered, it’s a whole different world)
  • knowing how to articulate and sell ideas really, really well
  • being super adaptable, on the turn of a dime
  • understanding how to test ideas, learn from the results, and redirect course accordingly
  • being resilient, even when it seems like everything’s going wrong
  • thinking creatively about solving problems
  • thinking innovatively, and being able to come up with ideas no one’s ever tried before

Relying on experience as a source of knowledge limits you to a chronological progression of growth — one that’s constrained by how quickly you can accumulate experiences. It might take years to encounter enough problems and come up with enough solutions to really learn how to think innovatively and start to pitch ideas that have an impact.

When you don’t have experience, borrow someone else’s. The fastest way to level up is to read — a lot.

When you read, you get to immerse yourself in the thoughts and ideas of people far smarter than you. It’s the equivalent of landing a dinner with one of your professional heroes, and getting to ask them questions all night, and then getting lucky enough to have them accept your invite to go get drinks once dinner is over, at which point they’re answering questions you didn’t even know you had.

And even once you have leveled up, keep reading. If you rely solely on your own experiences and perspectives, your growth trajectory is limited by the linear and chronological pace of your own development. If you use books as a window into other people’s experiences, you blow your knowledge-acquisition potential wide open.

The following is a collection of some of the books that have been most impactful to me on my own journey as a professional, and the ones I’d most highly recommend to others trying to level up their startup game.

The Essential Classics:

Zero to One by Peter Thiel

This is the classic playbook of the startup world. The subtitle says it all: “notes on startups, or how to build the future.” Thiel boils down the lessons he learned through starting PayPal and Palantir into 12 chapters of pure wisdom. I reread it on the regular.

This book will help you understand how startups work, and it will give you a window into what it means to think innovatively — one of the most important skills to have if you want to really crush it in the startup space.

Thiel talks about:

  • What it means to go from zero to one. Zero to One means going from nothing to something (inventing something that has never existed before, like the Wright brothers building the first airplane). One to N means innovating on something that already exists (like Boeing releasing the 737 MAX). The best companies always want to start from zero, and create something entirely new.
  • How the paradigm around innovation and growth has changed over time, and what that means for business.
  • How all the most successful people know secrets, and build their companies around the secrets they’ve discovered about how the world works. There are lots of secrets left to be discovered in the world, and our job is to find them.
  • His philosophy around hiring and building great teams
  • The importance of coming up with ideas no one has ever thought of before (and what this looks like in practice)
  • The importance of thinking about the best businesses as monopolies.

Niche Down by Christopher Lochhead

This book starts with the idea of thinking innovatively/finding your monopoly and takes it one step further.

Niching Down means finding your niche — the smaller, the better — and then completely dominating it. That’s how all great companies are built. Lochhead explores great companies that have found their niches, and breaks down what makes each one so impressive.

It’s a phenomenal book that will help you understand markets, categories, customers, and the power of being really specific.

I’d recommend Niche Down as a starting point, but Lochhead has a lot of other content that’s valuable to explore. He’s the co-author of another book, Play Bigger, which talks about category creation (not competing against other products, but rather inventing an entirely new category of products), and he’s the host of two phenomenal podcasts.

He’s also a fun author and speaker. He calls himself a pirate of the startup world, and it’s an apt descriptor. He’s as colorful as he is smart (The Economist once called him “offputting to some,” and he was so proud of the title he put it on his website’s About page).

The Hard Thing About Hard Things by Ben Horowitz

This is a book for CEOs, not employees, but it’s an invaluable read no matter who you are. As an early employee, one of the most confusing things is the way executives think. It feels like there are lots of curtains and secrets, and a lot going on that you sense is there but never get to see.

This book is the distillation of everything Horowitz learned in his 8 years as CEO of Opsware — one of the fastest-growing companies in the country during the dot-com boom, which had its IPO after the bubble burst, had to lay off large numbers of its employees four times, and eventually sold to HP for $1.6b.

This book breaks down what’s going on in the head of a CEO, and what happens behind the scenes. It offers a window into the things you don’t usually get to see a an entry-level employee, but that are critical to understand in order to grow.

It’s also a great book to read if you’re ambitious and know you want to rise up quickly in a company. It gives you some toeholds as you start to understand what you need to be thinking about in order to grow.

It’s also a great book to remind you how gritty startups are, and how much grit you’re going to need if you’re going to make it big.

The Inner Game of Tennis by Timothy Gallwey

This is a tennis book, not a business book, so it may seem odd to see it on the list. But Inner Game of Tennis is one of the most important books to read to level up your game.

The author of this book is a professional tennis coach. Over the course of his career, he started to see patterns in the way people learned — and realized that the biggest differentiator between people’s success was what was going on in their heads. He started experimenting with the way he gave people directions, the way he coached, and the way he helped people understand the game — and over time, he pivoted his coaching from teaching tennis to teaching the mindsets that are pivotal for success.

Just like in sports, your level of success in your career is going to hinge on what goes on between your ears. The sharper your mental game, the sharper your game in the real world is going to be.

The Magic of Thinking Big by David Schwartz

I’m a big fan of books written in the first half of the 20th century, and while 1959 doesn’t quite hit that mark, this book still has that old-school feel. Take a look at this quote from the opening chapter:

“The most essential element — in fact, the essential element — in our space explorations today is belief that space can be mastered. Without firm, unwavering belief that man can travel in space, our scientists would not have the courage, interest, and enthusiasm to proceed.”

In a similar vein to The Inner Game of Tennis, this book is all about what’s going on in your head. Your inner game is just as important is your outer game in the startup world. You’re creating something out of nothing, and running up against hard challenges, and pushing yourself farther than you thought you could go.

How you think makes the biggest difference in how you perform. Your level of success hinges on what you believe. The first step to succeeding is believing you’re able to succeed.

This book is all about getting your head in the right space, and establishing elite thinking. It also talks extensively about learning how to observe the people around you, and how they think, and how to adopt the mindsets you see in other people’s thinking.

The War of Art by Steven Pressfield

To be successful, you’re going to have to create stuff — the more the better — and you’re going to have to ship that stuff out into the world. Creating stuff is hard. Shipping it is even harder.

In The War of Art, Steven Pressfield talks about why shipping is so difficult — because of a force called Resistance, which is always present and always equal in measure to the importance of the thing you’re trying to accomplish. When you sit down to watch Netflix, you don’t feel Resistance, because what you’re trying to do isn’t worth much. But if you try to get up and clean your room, you’re going to feel a little bit of Resistance, because that activity has value. And if you decide to scrap all of the above and go write an article, let along a blog post, the force of Resistance is going to recognize that as something that’s both valuable and hard, you’re going to feel a lot of adversity in getting started.

Pressfield also talks about how to combat and overcome resistance, to be a consistent creator — and why it’s so important to do so. This is a phenomenal book to re-read on the regular. It will reset your creative process every time you pick it up.

The Best Articles and Essays

How to Get Work Done: A Primer — this one was a post on the Praxis blog written by my friend and colleague Chuck Grimmett. It’s a masterful overview of how to think about working and efficiency.

How to be Successful by Paul Graham — a phenomenal essay on thinking about your success and career growth.

Breaking Smart by Venkatesh Rao — a brilliant essay “miniseries” built off of Marc Andreessen’s quote “software is eating the world.” It explores how technology is changing everything in the world around us and gives you an edge in thinking about the future of the tech/startup world.

The Ultimate Gide to Writing Online by David Perell — the best professionals are writers too, and the fastest way to accelerate your career is through writing. David breaks down writing as a tool not only for communication, but for learning. This essay is a great resource as you’re building your career.

7 Essays That Will Help You Succeed in Internet Business by Taylor Pearson — this collection of essays is a great set of resources on thinking about your career. While it’s written for “internet business,” it’s highly applicable to all things startup, and should be studied thoroughly.

Patrick Collison on doing things that don’t scale — this is a talk, not an essay, but it still deserves a space on the list. It’s a great piece on thinking about getting in the weeds as a strategic move, to help you a) make your customers happy, and b) obtain the information you need to build systems that do scale.

Six Principles for Making New Things by Paul Graham — the title really says it all. A great essay on thinking about innovation.

The Most Important Points:

Make up for your lack of experience with the work of those who are smarter than you. They were generous enough to give you a window into their thought processes. Take advantage of them.

Pursue resources that help you gain knowledge not only about how startups work, but how innovators think. The history of innovation is one of the most important things to understand. It tells the story of all the people who saw things that didn’t yet exist, which are now part of your day-to-day world.

How to Become a Coach

I was 20 years old when I took my first coaching session. On the outside I was smiling, relatively cool, relatively collected. I was acting the part of the coach. I was here to solve problems — I got this.

On the inside I was terrified. I was plagued by questions — “Am I qualified for this? What if they ask me a question and I don’t know what to say? What if I’m not helpful at all? How do I know if I’m actually a coach?”

I had no idea what I was doing going into that call. I’d signed up to be a coach and I was taking my shot in the dark.

I shot and I hit. It wasn’t fancy, it wasn’t beautiful, but I hit the mark. I got on that call and I coached.

When I came out the other side (having answered the client’s questions and helped them identify the direction they needed to move to start solving their problems), I was on an adrenaline high. I did it. I’m a coach!

It turned out I had known what I was doing — I just hadn’t know it.

Storytime aside, here’s the TL;DR version of my answer: start coaching.

If you want to be, do. It’s quite simple.

More on how to do that in a second. First, let’s talk about what a coach is and doesthen we’ll talk about how to start.

A good coach is able to:

  • listen really well (your client always wants to feel heard)
  • ask questions that help the client identify their problems
  • help brainstorm solutions for the problem
  • help their clients put together a plan of attack for implementing those solutions

If you boil it all down to the simplest terms, that’s really all a coach does. There are lots of different types of coaches, with different sets of qualifications and specialties. Some will be experts and propose solutions. Others will just walk with you through the process of finding solutions for yourself.

Your approach will depend on the level of expertise you bring to the table, but most beginning coaches will start out just walking beside their client (I like to use the word “facilitating”). That’s certainly what I was when I started out.

You don’t need expertise to start. All you really need are people to coach.

To become a full-time coach, you’ll need other things too — a little business savvy, a brand, and a steady source of income. Each of those topics deserves a post all to itself. I’m just going to focus here on the raw coaching itself, and all that requires are the people to work with.

So where do you find those people?

I’m going to backtrack for a second — because how does a 20-year-old college opt-out (no credentials here) get a paid coaching gig?

Full disclosure, it was a long road to get there. I started developing my coaching muscle in high school, while I was working as an editor. Being an editor requires a) helping people refine/get better at what they do, and b) explaining the logic of the changes you’re making, so the people you’re working with understand them too. Editing made me good at teaching, and at seeing where people were struggling and needed to get better.

After I graduated high school, I decided not to go to college, and I started teaching writing classes instead. I worked with homeschooled kids age 7–14, and I learned a lot about teaching, mentoring, and facilitating people while they refined their capacity as writers. I got even better at communicating the places I was seeing where my students needed to improve.

When I started working for Praxis in August of 2016, I was in the operations department, but our team had a full staff of coaches (since we’re an education startup!). I’d been at the company for almost a year when I finally pitched myself to become an advisor — and when our education director said yes, I put my profile and my Calendly (pictured above!) up on our private participant site. I was so excited when I got my first booking — which then turned into nervousness, and then terror, and then excitement again when I not only survived my first coaching call, but proved myself as a valuable resource.

I’ve been coaching with Praxis for almost two years now, and full-time for a year and a half. I train our coaches now, too. So what I did seems to have worked. 😉

To turn the above story into general advice:

It doesn’t really matter where you start. The most important thing is to find people to work with and start coaching. Once you start to get reps under your belt, you become more legit. People start to notice. You become more confident. It starts to get a little easier.

If you don’t have a track record as a coach, finding existing structures to coach within will help you get off the ground (like I did by working as a writing teacher, than as a coach at Praxis).

If you don’t want to work within an existing structure, find a pain point you can help people resolve and start to create a niche around it (helping young people figure out what they want to do after high school? Helping yoga teachers turn their passion into a business? Helping writers actually sit down and write, and finally break through their creative block?). Make sure it’s something you know something about, but don’t worry about being an expert. You’ll become an expert through the act of coaching.

Take some clients for free to start, to get testimonials and experience. Ask for referrals.

Over time, you’ll start to build up a client base — and with each new client helped, every new problem resolved, you’ll become a better coach.

And again — do not, I repeat, do not, worry about being an expert.

I’m going to reference that story I told again. Remember how terrified I was?

If I’d waited until I was “ready” to coach, I never would have started. Two years later, I still wouldn’t be coaching. I’d probably still be too scared to start — because I’m still not an expert, and no amount of “preparation” can ever make you ready.

Have you heard the adage “we don’t know what we don’t know?”

Here’s the other side of the coin, and one of my favorite truths about life: we also don’t know what we do know. I learned this on that first coaching call — and the countless calls and meetings I’ve taken since.

We have a lot of information we collect on a daily basis but never force ourselves to actually stop and acknowledge. You don’t realize you have this information until someone asks you a question and you’re in a situation you have to answer — or at least try.

You might panic a little. You ask clarifying questions to stall for time, while in your head you’re trying to figure out a way to tactfully say “I’m sorry, I don’t know.” And without realizing it, your stalling questions turn into resolutions to the problem, and your client is happy, and you’re happy too, because you’re coaching and it’s working.

The point being: you don’t have to know everything to be a coach. Don’t expect yourself to, and don’t use that as an excuse to not begin.

If you want to be a coach, start coaching.

Note: read the original Quora post here!

The Fine Line Between Poetry and Truth

As a writer, it’s easy to fall in love with the words.

They have such beauty to them, after all. Such form. When you say them, they sound musical. When you write them down, they grace the page. It’s like magic; the results are like a drug. They make you giddy.

Your writing is not matter-of-fact; it’s art. You are not mere scribe, but poet.

Many writers have fallen into an endless love affair with their writing. It’s no crime — it happens. It’s happened to many of us. But it is an ineffective mode for telling the truth — which is a writer’s ultimate goal, even when the truth is entirely made up.

Hemingway said it best — “just write the truest sentence you know.”

This requires you to be true to the ideas, not the words. The concepts you’re trying to get across, not the words you’re choosing with which to do so.

You must treat this as principle, as absolute: Content over words. Ideas over poetry. Always.

You can’t sacrifice the right word for the prettiest one, nor the most musical turn of phrase at the expense of saying what you truly mean.

It’s easy to get caught up in the beauty of your words and steer away from the truth.

For example — Faulkner and Hemingway. Faulkner is a writer known for his love of the sound of his own voice. He wrote paragraphs that seemed to stretch for miles — on and on and on. And that’s the edited version. He loved the words so much he got lost in them, was consumed. On the flip side, Hemingway was a pragmatic man, anchored in reality and constantly grappling with it — and his work reflected that. Before he spoke of writing truth, he’d already found it — for himself.

Words are beautiful. In shapes and designs, they become art. Their beauty compounds. They take your reason away, like a hard drug; disillusioning.

Make sure you never sacrifice truth in the name of beauty, nor pursue beauty from a place other than truth.

How to be Successful Without a College Degree

I recently came across the following question: “How can you be successful without a college degree?”

This is one of my favorite topics — and the answer is much simpler than we’re often led to think.

You become successful without a college degree the same way you’d become successful with a college degree — by building skills, building a portfolio that showcases the ways you use those skills to create things of value to other people, and using that portfolio as leverage to work your way into positions of greater and greater responsibility (which, typically, is equated with “success”).

For example, imagine you want to work as a marketer. Here’s how this might look in action:

Step 1: learn how to run Facebook ads (building skills)
Step 2: run ads for small local businesses at a low cost to gain experience (building a portfolio)
Step 3: use those as examples to land a marketing role at a startup (leveraging your portfolio to gain a position of greater responsibility).

Once you’ve gotten your foot in the door with that first role, the process repeats — create evidence of your ability to be valuable (bringing in clicks/subscribers/purchasers through your marketing work), and then use those results as leverage to sell yourself for a higher-paying role at another company, or for a promotion.

The thing employers are looking for is your ability to create value on the market. That’s all.

Their opinion on what’s required for being successful on the market (the hard and soft skills you need to bring to the table) might vary, but the underlying principle is the same

Having a college degree doesn’t change your process for success at all. With or without a degree, the approach is the same — build skills, create (and showcase) results, use those results to sell yourself for better opportunities. Rinse, repeat.

Here’s the thing that most people don’t talk about: employers don’t actually care whether or not you have a degree.

A degree is just a proxy for your ability to create value.

I want to be clear on the logic behind why you don’t need a degree to be successful, but to obtain that clarity, we’re going to have to get into the weeds for a minute and get philosophical.

Bear with me.

A proxy is a substitute — a stand-in. In this case, a college degree is a proxy for your ability to create value in a job.

Here’s another example: money is a proxy for value. Fiat currency doesn’t actually have inherent value. It’s just a way of measuring the amount of value people owe each other.

A college degree is the same way. It doesn’t actually tell employers what skills you bring to the table, or what your individual potential is for being useful/creating results. It’s a generalized way of measuring someone’s predicted ability to create value, based on a set of hypotheticals (the person successfully completed college, which hypothetically signifies that they can: commit to something until it’s finished, consistently show up and get things done, communicate, think critically, manage projects, etc.).

The things the employer actually cares about are the things the degree signifies, not the degree itself — the same way someone who has $20 doesn’t actually want the piece of paper, but rather the things that piece of paper signifies (your ability to purchase $20 worth of things).

Having a college degree isn’t even that great of a signal of your ability to create value. Lots of people have them, but still aren’t effective in the professional world. And even if you have one, there are a lot of missing links of information an employer is looking to fill — like your ability to complete the actual tasks you’d be responsible for in a business. (Having a marketing degree doesn’t mean you can effectively drive results in a Facebook ads campaign. You have to have a Facebook ads campaign under your belt to prove that).

Which is why, degree or not, you’ll still need to follow the above formula to obtain success — build skills, create (and showcase) results, leverage results to land higher positions, ad infinitum.

Here’s another data point to consider: after a couple years in the professional world, people stop caring whether or not you have a degree at all. They care about what you’ve done and what you’re able to do, not where you went to school. Once you have some experience on your resume, nobody even thinks about your degree anymore.

Here are a few practical pieces of advice to help you not only execute on this process, but excel at it:

  • Build a digital footprint. We live in a digital world. If there isn’t digital evidence of your work, it doesn’t exist. Write blog posts, answer questions on Quora, establish your LinkedIn, post your projects on an online portfolio. Document everything of value you do. Anything you don’t document is as good as shorting your own stock.
  • Work hard. This is another absolute that’s consistent both with and without college. No matter what you do, you won’t be successful if you don’t put in the work to earn it. Success is a derivative of effort.
  • Don’t be too precious to do hard things. You have to pay your dues before you can rise.
  • Don’t hold out for the “perfect” opportunity. Take the opportunity that’s right in front of you, and then leverage it into something better. There’s no such thing as a perfect opportunity, only a perfect time to start — which is right now.
  • Get smarter. Make building your knowledge base your most consistent hobby. If you can, become obsessed with it. In its ideal sense, college is designed to make you smarter. Depending on the college you go to, it’s possible to make it through without becoming smarter at all — but if you embrace anything from college, it should be the ideal of knowledge. Knowledge — information — is one of the most important factors in the equation of success.
  • Stay curious. Cultivate your curiosity as much as possible. Curiosity is the road that leads to knowledge (which fulfills the point above), but curiosity is an end as well as a means. Build your curiosity muscle. It will make you better at tackling and solving problems — which, in turn, will make you a more valuable employee.
  • Maintain a definition of success. Don’t be afraid to change it as you learn and grow and evolve (because it will change — probably often), but make sure you always have a definition — and make sure it’s one that’s created based on your own values, not general societal definitions of “success.” Everyone’s idea of success is different, and knowing what yours is (what you’re striving towards) helps you bring purpose to your work— and purpose is the fuel that drives you forward.

This post was originally inspired by a question on Quora. Read the full thread here.

Photo by David Beatz on Unsplash

Quora Answer: What are the Benefits of Not Going to College?

There are a variety of benefits to not going to college. College is an expenditure of a number of resources — time, energy, money, etc. If you aren’t using those on college, you can be spending them elsewhere — namely, on something that’s in more direct alignment with your goals.

A few tangible, easy-to-measure benefits:

  1. You save money. Even if you’re working with scholarships, college is expensive; $20,000-$60,000/year is a steep price to pay as you’re starting your adult life. It isn’t guaranteed to pay off.

    Debt is a limiting factor in your decision-making process. You have to make choices that accommodate that debt until you pay your bills off — which will take years. Nearly 40% of students default on their loans.

    Not carrying the burden of debt means you’re able to make strategic financial decisions without factoring for your student loan bills. You can take a lower-paying but more strategic jobs. You can use that $20,000-$60,000 a year on something else — cars, a house, travel, other training resources, etc. College is a general investment. What specific investments might you make with that money?

  2. You save time. Why spend four+ years in school when you could be spending that same amount of time getting four+ years of working experience?

    In a lot of careers (especially in the business world) experience makes you more valuable than a degree does. Getting four years of experience means you’re four years ahead with savings, earning potential, competence, and status.

    Arguably far more valuable than four years of theory (but no real-world, tangible proof of your ability to create value in the workforce).

Those two quantities are objective and easy to measure — but there are a lot of other variables to measure, too.

College is a very general thing — a one-size-fits-all formula for launching your adult life. While it’s more specified than high school (different majors, etc.), it’s still a generalized system moving you towards generalized goals. There’s a lot more room for customization if you’re following a unique and specific path.

If you want to run a travel photography business, college might help you get there — but there may be much more direct ways of obtaining that goal (picking up photography gigs, building a presence online, networking with people already established in the space, establishing mentors, funding your own trips to build up your portfolio).

If you want to work in business, you might be able to get a degree in business from college — but going and working for a couple companies, gaining resume experience, building skills, obtaining references, and building your real-world competence is a much more direct route.

You’re working with finite energy and resources. The benefit of spending those resources on the most direct route to get you where you want to go is very high. If college isn’t the most direct route to get you where you want to go, then the benefits of not going to college will be substantial.

And as an extra bonus — not going to college makes you interesting. The world is becoming more and more friendly towards people who aren’t traditionally educated (the questions around college are becoming more and more prevalent) — so people will be tolerant of your decision, but they’ll also be interested, because you deviated from the norm and did something unusual.

Unusual = interesting.

Interesting = the formula for a good story.

Humans are storytelling creatures. We’re compelled by good stories. So on a human-interest level (and most of our interactions are impacted by human interest), you’ll get people’s interest when you tell them you didn’t go to college — and that’s beneficial too.

Read the full Quora thread here.

How to (and How Not to) Measure Value in Opportunities

My colleague T.K. Coleman says “If you want to be a developer at Google, don’t go be a developer for another company. Build your development portfolio on the side and do anything you can to get in with Google, even if it means sweeping the floors.”

There are two reasons why this is a valuable approach to take:

  1. It allows you to build relationships within the company. People hire and promote people they know and enjoy working with. The stronger your network, the stronger your potential for opportunity. In most cases this is a direct correlation.
  2. It allows you to better understand the company. When you’re on the inside, you’re constantly learning — about how the company functions, about the company’s philosophy and ideas, and ultimately, about its opportunities (which is what you’ll need to capitalize on in order to grow).

Here’s the key to this whole philosophy, though — sweeping the floors at Google isn’t just about doing time until you earn a spot on the development team (which in and of itself is a circuitous process, and will likely take a number of jumps from role to role before you make it to your final destination as a developer).

This is so important I’m going to say it twice — it’s not just about doing time.

Again, there are two important reasons why:

  1. “Doing time” implies that, if you fulfill your time commitment, there’s a guaranteed end result, which there’s not (you have to earn this stuff!)
  2. It implies that there’s only a payoff if you fulfill your time commitment and land the full-time offer. It implies you’re only getting something of value of you get the end result you’re looking for — and that’s a deeply limiting thing to believe.

Here’s the thing: both parties in this relationship are free agents, and that limits the potential for guarantees. There are so many variables at play. You might not do anything beyond sweeping floors to get attention, and therefore never open up opportunities for growth. Google might not need you. Google might have needs, but you might not be a good fit. You might sweep floors for six months (or even work your way up into a customer success or support position) and then realize that you don’t want to be a developer after all, or that you actually want to be a developer at a different company.

But, more importantly, this is a limited (and limiting!) mindset. It’s only counting the end result as a worthwhile measure of value — when really, that end result is a small piece of a very big puzzle, and a single source of value (out of a large number of sources).

Think about it: if you sweep the floors for six months and realize you don’t want to be someone else’s employee, but rather start your own company, is that wasted time?

It is if you only measure the value of outcomes based on a success/failure metric. You didn’t get the developer role you were shooting for. You failed.

But there are so many other forms of value you’re overlooking. In this scenario, you’re smarter than you were before. You have a better picture of how you want to move through life, and the things you want to be building. You’re better off (and better equipped for success) than you were six months prior when you started sweeping floors.

Might, then, this also fairly be measured as a success?

Even if you get let go (i.e. the opportunity ends, and it’s not on your terms), it can still be chalked up as a success. Maybe after six months Google goes through restructuring and lets go all of its floor sweepers. Might that also be measured as a success? You may not have landed an opportunity, but you have a better understanding about how a company like Google is structured internally. You’ve learned more about tech startups by being immersed in one. And you have some experience under your belt. You’re still better off than you were before you started.

Rather than thinking about success in terms of outcome, think about it in terms of internal value. If you’re smarter, or stronger, or faster, or more competent, or more skilled than you were before you started (even if it isn’t in the ways you initially intended) if you’re measurably different in a positive direction than you were when you started, then value has been derived from the experience.

This is a valuable way to analyze past experiences, but it’s also a valuable way of analyzing the opportunities in front of you.

I did an interview last week with Isaac Morehouse for his new podcast Career Crashers (episode should be releasing this week or next, so link coming soon). In the interview, we talked about my journey from college opt-out to career coach at Praxis — how I decided not to go to college in the first place, and how I built my way up to becoming the Apprenticeship Advisor and Community Manager at Praxis.

One of the points we talked about was my journey from intern (how I started working at Praxis in the first place) to full-time employee. The journey was a slow one — it took more than a year for me to ultimately land a full-time role. This is, in part, one of the realities of setting your sights on a small startup. The keyword in the last sentence is small — the staff isn’t substantial, opportunities are limited, and bringing on a new team member is a big deal (and a big investment). It isn’t something that’s done lightly, nor often.

I worked as an intern — and then as a contractor — for a long time before I was brought on into a full-time position, and throughout, the guarantees of a potential role were tenuous., and purely speculative I was never guaranteed a full-time offer, and it certainly wasn’t my reason for staying. I wasn’t busy holding out for a full-time offer. I was learning and growing in the role I was in.

Of course, I wanted the full-time position, so I could spend all of my time doing the work I loved. But the full-time role was never a measure of success in what I was doing. I was working for Praxis because it afforded me the opportunity to grow in ways I wanted to grow, gain experience working at a startup, gain proficiency and aptitude as an educator and a coach, be around my favorite thinkers writing about the alternative education space, and become a better and stronger employee and person. If things had turned out differently and I’d never ended up working full-time with Praxis, it still would’ve been time well spent, because it made me as an individual better.

Titles are an easy proxy for measuring value — that’s part of why we crave them. It’s a good thing to covet specific roles and jobs, especially as you grow in your career. But when you’re building towards something — especially if you’re in the early stages of your career, and have lots and lots of room to figure things out — don’t limit yourself by measuring the value of an opportunity based only on outcome, and don’t be afraid of taking a circuitous route to get you where you want to go.