I'm not a model of success. I haven't founded any startups or started any popular blogs; I don't even have a passive income.
What I have done is start a career in content marketing. What I might lack in expertise, I (hope) I make up for in relevance for anyone just starting out.
I started my content marketing career, officially, by title, in 2019. I had my first writing job for a year and a half before that.
This post is a personal, non-comprehensive list of tips, lessons, and principles I've learned, and thought hard about over the intervening years.
Your experience has varied or will vary, but I think there’s often something usefully general in the sufficiently personal. That's what I'm focusing on.
Nothing I prescribe is actually necessary, but if I could go back in time, I'd require it of my younger self. That's the best prescription I can offer.
How I started my content marketing career
I never dreamed of content marketing, nor did I even dream of marketing. Through high school and college, I assumed marketing was synonymous with advertising.
I wanted to be a novelist. But the unlikeliness of that possibility gnawed at me. Occasionally, the gnawing would hit a nerve and I'd declare a new path: psychologist, professor, editor.
Editor was my last chosen life raft when I graduated, so I went with that. I went to graduate school because the working world seemed to require experience I didn’t have.
A year in, I took a course on content marketing. I had only planned to learn more about "web publishing," but the subject consumed me.
I was, and am, in content to create and to help. I like creating things that help other people do things. That's what it comes down to. I'll learn all manner of tactics, skills, and strategies to make things that are more helpful, and to better distribute them to the people that need help.
I'll analyze my lead up to content marketing more in the following sections but know first that I come to this career obliquely.
Here's my timeline:
I was an English major throughout. Junior year, I declared a Professional and Technical Writing concentration. I graduated with a 3.9 GPA. I worked summers as a bagger at a grocery store, host at a restaurant, and a minimum-wage internship at a food and wine magazine.
2014-2015: College Associate.
I worked a yearlong, temporary position as a glorified teaching assistant/admin assistant, mostly to get paid while my partner finished her last year.
2015-2017: Moved to Massachusetts
I moved from Maine to Massachusetts on the promise of a technical writing job that fell through. I then worked various retail jobs: baker, merchandiser, candlestick maker.
2015-2017: Emerson College.
Meanwhile, I pursued an MA in Publishing and Writing at Emerson College in Boston. I don't recommend it.
2016-2018: First writing gig
I worked as an Assistant Editor for a technology business site, writing and editing content for IT administrators.
2019-Present: Content Manager
I'm now a Content Manager at Animalz—a fully remote content marketing agency. I get to write two articles a week for exciting tech companies, develop and track ambitious content strategies, and work with the smartest group of people I’ve ever met.
Below, 15 things I’ve learned that have gotten me this far and, more importantly, will propel me even further.
1. Don’t apply to hundreds of jobs
I've applied to about a total of 80 jobs in my entire life. I kept most of the resumes and cover letters so this is a pretty accurate count. Not even a fourth of those were for content marketing jobs.
The fewer jobs I applied to, the higher my proportion of success was.
Common sense tends to be the opposite. I've seen advice to apply to dozens of jobs a day, hundreds a week: anywhere in the country or the world for any remotely related role. Anyone who says this will follow up to say that you should of course tailor your resume and cover letter to each job.
But they don't mean it.
The logistical incentives don't line up. So don't do it that way.
Figure out what you really want to do, and what you can actually convince others you can do. Put all your effort into the jobs. Track the careers page. Follow employees on Twitter. Read their blog.
When you apply, write a resume and cover letter that's made for them. If you communicate one thing to them, show that you know them, and you want to work for them. Like, really know, and really want.
2. Build a support network
Entry-level is hard. Find friends and family who believe in you—fancy job or no. Early on, that's more important than a professional network.
Much of this article, for instance, was inspired by discussions with my partner. I wouldn’t have articulated or codified any of this without that support network.
3. Demonstrate internal motivation
Companies want to see motivation, but it's a hard thing to show.
Some cover letter advice will tell you to demonstrate your desire to work for the company you're applying to.
It's more important to demonstrate an internal motivation that carries you from your origins to that company—and beyond.
Write a narrative that supersedes any one job or client. A good company will know how to exploit and direct that energy. They don’t want to have to keep applying external motivation.
If your only motivation is to get the job or do the work, they can't trust you to keep going when work gets tough, or the challenges change.
The more distant your goals, the more impact-based and open-minded to means they should be. If you can convince a company that they can be a means to your goals and vice versa, you can turn a job opening into a moment of serendipity.
You want your employer to feel lucky they found you too.
Life has no narrative. It’s nonlinear and complex. It’s up to you to make a narrative—it’ll become true as you pitch it and live it.
Maybe you only discovered content marketing recently. That's fine. Don't focus on that. Focus on the narrative that supersedes it.
In my case, it was my desire to help people at scale. There's a lot of ways to do that and the means I described shifted depending on who I was talking to, and how I was most recently thinking about my future.
Don’t be afraid to feel like you’re lying. I've explained my ambitions to companies many times, and it felt wrong at first. I was so far away from living up to them. And they'd change as I tried to live them out.
That doesn't make them wrong though, and it doesn't mean you shouldn't explain them confidently; it just means you're figuring it out as you go, just like everyone else.
4. Turn your job search into career research
Applying to jobs is awful. It feels awful. You're inviting rejection, and it's dispiriting.
I used to dread opening up Indeed, scanning through listings, and feeling not good enough. I'd internalize it sometimes, and wallow for weeks without even emailing anyone.
Don't do that.
I did that because that was the only way I knew to look for jobs. But I eventually stumbled into a better way.
The job search sucks because you're one person, looking for one thing, in a world of options that almost always rejects you. If you don't reframe it, it'll always be failure after failure.
Instead, use all that time to learn more about your career and your industry.
Job listings are better sources of career information than any career counselor, industry guide, or helpful manager. Advice is good, but companies are accountable to their ability to get employees, and you can learn a lot from what they look for.
The first step in this career research project, for me, was to put "content marketing" or "content writer" as a keyword into some job search engines (I recommend Indeed, Lensa, and We Work Remotely to start). Depending on how much energy I had, I'd also enter similar roles like "assistant editor" and "technical writer."
Emails will overwhelm you. Many of the listings will be repetitive. But your job isn’t to pore over every one.
I built a content marketing career database.
Every time I saw an intriguing job listing, for me today or me in 10 years, I made an entry. Each entry included the company's name, a link to its careers page, its size, what it did, and whether it was remote.
This started as a simple bulleted list but eventually evolved into a Notion spreadsheet.
The more comprehensive my database became, the less I needed to rely on email notifications. Once I had a new resume I wanted to try out, I could click through my list and see who had openings.
I started to see a distribution of jobs.
Some companies only ever wanted mid-level or senior content marketers. Presumably, their teams were small and they only wanted people who didn't require much training.
Some companies had numerous senior level positions. They tended to emphasize "content teams" rather than direct reports ("you'll be working with X team" vs. "you'll be working directly under VP so-and-so").
Only a few companies actually seemed to regularly hire entry-level content marketers. They often had bad reputations: long hours, low standards, high stress.
I also started to see a distribution of skills.
Jobs with the same titles emphasized different skill sets and tech stacks in different companies. One "content marketing manager" might need to set up a studio and produce videos; another might be a full-time writer; another might design landing pages, email funnels, and PPC campaigns. "Manager" might mean you manage employees, clients, or content—or none of the above.
My database showed me I couldn't be all things to all roles—at any level. I couldn't start anywhere; I had to start somewhere.
5. Break jobs into their component parts
Job listings are wish lists, and companies often wish for a lot.
One listing might say they want you to know how to interview, optimize for SEO, and write. It'd be logical to think you need all three, but in many situations, they'll be willing to train you on two if you know one.
Look at their content. If their writers are publishing a lot, you can assume that writing really is a necessity. If some posts are written for social or newsletters, or if they are written for SEO but badly, then you can guess SEO knowledge is more of a nice-to-have. They'll likely train you or learn with you.
As you start to break jobs in your industry and vertical into component parts, you can figure out which skills are most valuable. In most content marketing roles, writing skills are non-negotiable. So get good at that first.
Use the skills you do have as leverage. I pursued a business journalist role because I knew I had the writing skills and the industry curiosity. They taught me SEO (among other things), and when it was time, I leveraged those new skills to get my current position.
When you break jobs into component parts, you'll start to see different trajectories. Don't pursue a marketing assistant job because it's the lowest job in your category. You don’t need to start at the bottom rung to climb.
6. Build and leverage collateral
I don't have any special resume or cover letter suggestions to offer, so I instead recommend adding content to your application arsenal.
Some people will advise you to hustle, and build an entire blog or newsletter or social media fanbase. I don't doubt this is effective if you can pull it off, but it's much more practical to focus on one really good piece of content.
I felt the temptation, numerous times, to launch a project but the effort never fruited anything impressive. Depending on how much time or money you have, you might need to prioritize getting a job over building something independent.
This content should demonstrate your understanding of your niche and the valuable perspective you bring to the industry. One good article is better than a whole rickety operation.
Pin it to your Twitter feed so that people see it every time they click through to your profile.
I recommend owning your own platform, but it's not a necessity if the cost or time is impractical. My post was on Medium. It's also not worth worrying too much about going viral or optimizing for SEO.
It's easier for an employer to teach you how to write an optimized listicle than to teach you to be interested in the industry, and willing and able to offer an interesting perspective on it. The other stuff will come later—be interesting, first and foremost.
7. Find pragmatic inspiration
It's perhaps not surprising that marketers give out some bombastic marketing career advice. They're marketers, after all.
But if you only follow "rockstars," you'll start to think you need to leap numerous standard deviations beyond the mean to succeed.
First, embrace the possibility of being average. Most people are. Average people can be successful and happy and fulfilled.
Second, if you want to be great (whatever that means), you're going to have to keep finding things you're terrible at, and getting to average before you can be great. You're always going to need inspiration from people that are in relatable positions, doing things you can at least imagine doing.
There's a whole industry of people who profit on envy and followers who feed on self-deprecation. The success-thirst industry is fueled by outliers at best and frauds at worst.
I'd avoid it as much as you can. Find people like you and grow with them.
8. Make an accomplishment journal on Day 1
Get a journal before your first day on the job. No one will tell you to put a journal down like they would a phone, and you won't have to swipe away to another window when your boss walks by.
Write down every tool and process you learn. Every time you succeed, no matter how little, write down your accomplishment, the date, and what you did. The longer you're doing the tasks, the harder it will be to appreciate how hard they were to learn.
I track my successes and failures closer than my employers. You're working for yourself first, your career second, and your current job third. An accomplishment journal will keep you in that mindset.
9. Hard work is a vanity metric
Working hard isn't necessarily good, and it won't necessarily reward you.
As far as I can see, the inherent value of hard work came from a previous working world (most likely mythical) where there was always a boss to notice you coming in early, staying late, and cleaning up.
These days, if you're at the entry-level, you're most likely getting a running start for a series of job hops. It's a waste of time to impress your boss or perform dedication.
Instead of working hard, find points of leverage and press hard enough to create outsized effects.
Finding leverage might entail work that's invisible to people around you. At my business journalist role, I spent more time on SEO research than others. I received some skepticism for my lower article output but raised eyebrows for my higher traffic.
Pressing that leverage might entail a lot of hard work. But the hard work is incidental to your means and your ends.
10. Focus on your next job’s KPIs
When you get a job, you want to do well at that job. That's natural, but it primarily serves your boss. Your devotion to immediate tasks does you a couple disservices.
1. The only person you're working to please is your immediate boss
If you come in every day, and do what's assigned to you to the best of your ability, you'll likely please whoever assigned those tasks. That's all.
Your boss doesn't necessarily know much more than you do—especially at an entry-level job, where your boss might only be one "step" ahead.
The worse the company, the more likely you're trying to impress their translation of what their boss said to them. If your boss's boss demands more good articles, and your boss asks you to write more, and you sacrifice quality to meet demand, you'll end up with two displeased bosses, even if it's your immediate boss's fault.
It's always your job to understand the full context of your position, and the role it plays in the company at large. Only when you understand context will you figure out leverage.
You'll limit your progress to the progress others let you have if you let them express your limitations for you.
2. You risk only getting good at the job you have, rather than the job you want
If you master the tasks assigned to you, you'll become the master of doing those tasks. That's all.
Old people will tell you that you'll learn something about working hard or showing up on time or putting in your dues. They might also say raw effort will impress someone who'll give you a chance.
But why waste your time on raw effort when you could figure out a way to refine it? If you're looking to impress, you'll always impress more with the real thing than with evidence of it.
An example. At the business journalist job, our primary KPI was articles created, but I knew the KPI behind that was traffic. Instead of working as I was directed, I worked for the real KPI.
I knew my next job would be more interested in my ability to grow traffic than to churn out articles. So I carefully optimized every article to have the biggest effect it could. I produced fewer articles but more traffic.
No one could really criticize me (it was a pretty low pressure position, to be transparent), and no one really praised me. SEO was a factor, but it wasn't how they measured success.
This made me a “B” employee there, but it made me an “A” employee for different companies. But that's okay—I was working for my next boss.
11. Watch out for diminishing returns
Being entry-level is hard on your ego.
You have to believe you have a lot of potential but know you have little experience. When you interview, you end up arguing you'll definitely for sure live up to that potential you definitely for sure have.
If you're lucky, you'll find a company with great mentorship that's willing to cultivate and encourage you. Call me cynical, but I don't think there are many of those.
Extract experience, growth, and evidence of both. Then get out.
At many entry-level jobs, diminishing returns will begin early, likely way before you’ve mastered the job. Don't become perfect for a role you don't want at a company you don't like.
12. Pay isn't linear
I've worked a lot of minimum wage jobs.
When I moved to Massachusetts, I did so thanks to a job offer from an ed tech company. I did numerous phone interviews, drove down to an in-person interview, did a drug test, and signed an offer letter. Suddenly, they gave me hours that demanded I quit school. We couldn't compromise, and I lost the job. I worked many more minimum wage jobs after that.
Don't view pay linearly. My next job was salaried and paid me nearly double minimum wage. After an annual raise, I moved to my current job, which paid me almost double my prior job's starting pay.
When I was sketching my content marketing career plan, I imagined broad steps from $30K to $45K to $60K and on. Perhaps 1-3 years in any of those stages. But as it turned out, I spent a year and a half in the first stage and skipped to the third.
The next job was willing to pay me more for the skills I had built at my previous job. Because I focused on my next job's KPIs, I translated my tangential responsibilities at my previous job to core responsibilities at my next.
You won't know exactly how much though, so never offer your previous salary. There's a good chance you can get more than you'd expect.
13. Craft > passion
The most consistent career advice I've received is to "do what you love" or "pursue your passion." It sounds good, but I think it's misleading and impractical.
When you frame your career as a mechanism for facilitating happiness, you tend to limit your work to expressions of your passions.
With that frame, you might, like I did, pursue scarce jobs in an under-paying industry. I wasted a lot of time trying to become an editor at a prestigious book publisher. You have to do a lot of work to find a job so suited to your spirit that it doesn't feel like work.
Think about craft instead of passion. A craft is something that brings you satisfaction, not necessarily happiness. A craft is something that's rewarding to master, even—and maybe especially—when you struggle and fail.
The earlier you are in your career, the more you should focus on mastering a craft. This doesn't mean you have to hustle or work long hours. It means you need to explore what you can do now, and what you'll find rewarding even when it's hard.
I assume carpenters aren't passionate about chairs or plumbers about pipes. But I know they aren't unhappy. When I'm writing an article, I think in those terms.
Every day, I try to build something sturdy and useful, and that's enough.
14. Confidence > competence
Feeling incompetent is a sign you're in an environment that's challenging you to grow. But it's not proof.
Anyone can feel an imposter experience, a sense that you're faking the value you offer and you're poised to expose yourself.
Imposter experiences are primarily the result of bad work environments. Bad workplaces don't encourage growth or care about psychological safety.
Good work environments, however, don't necessarily make you feel competent. A good workplace instead encourages your confidence. If you're confident, you grow through your incompetence. You can embrace it.
As you start to build competence, be careful not to rest it on a fundamental.
Don't fall into the trap of thinking, as I did, that you've got writing mostly down, and you just need to learn some new optimization tricks. Nope. You're going to refresh those fundamentals for (I assume) the rest of your career.
You'll grow, but you'll learn new angles and apply them in new contexts. Competence is nice, but focus on confidence.
15. Beware of advice
All advice expires and neither the giver nor the recipient knows when.
I wrote this post as an attempt to optimize for relevance instead of expertise. I'm sure I'll eventually complicate, retract, or disavow some or all of it.
My hope is that this is a counterweight to advice that's wise but irrelevant.
This next part is hard for me to admit. My parents, professors, and advisors have all mostly led me in wrong directions.
My parents are lovely people, but their advice is 20+ years out-of-date. It's relevant to different industries in different areas in eras gone by. My professors were sometimes in the right industry, but their advice was decades older. At Emerson, many of my professors hadn't worked professionally since computers became a thing.
These were my two primary categories of guide and they failed me more often than they succeeded. Their intentions were always good (and they helped me out in many many other contexts) but the career world was simply too dynamic for them.
They'll be a broad swath of other advisors too, especially online. Their advice will often be out-of-date too. If they're tweeting or blogging into the air, it'll also likely be simplistic: do Work A and get Success B.
The longer they've succeeded, the more likely their experience will suffer from survivorship bias. They won't know which of the many things they did that led to success. Luck played a role they won't be able to quantify.
Don't consume advice as rules. Listen deeply and widely, but listen for ideas that'll last. Extract principles and methods—then move on.
Principles will keep you focused, and methods will help you move faster and better. Otherwise, get active and generate experience you can learn from. The best advice is first-hand.
I hope this is helpful! Now, move on.