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.

I started my content marketing career, officially, by title, less than a year ago. I had my first writing job for a year and a half before that. Getting into and then out of the entry level was really difficult, really stressful, and I felt alone most of the time. This is the advice I wished I had.

What I might lack in expertise, (I hope) I make up for in relevance to anyone just starting out.

This post is a personal, non-comprehensive list of tips, lessons, and principles I've learned. Your experience has varied or will vary, but I think there’s often something usefully general in the sufficiently personal.

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 planned to be a novelist through high school and college. 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 I thought the working world only opened to those with pre-experience. (I was wrong.) 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 eventually discovered that's essentially what I've always wanted to do.

I'll analyze my lead up to content marketing more in the following sections but know first that I came to this career obliquely.

Here's my timeline:

2010-2014: College.

English major throughout. Junior year, I declared a Professional and Technical Writing concentration. I graduated with a 3.9 GPA and highest honors. I now consider most of that academic effort a waste of time. I worked summers as a bagger at a grocery store, host at a restaurant, and minimum-wage intern 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: Moving to and around Massachusetts

I moved from Maine to Massachusetts on the promise of a technical writing job that fell through. I moved around a lot and worked various retails jobs: baker, merchandiser, candlestick maker, etc.

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–and I get to write two articles a week for ambitious tech companies. I love it.

Here are 15 blunt, honest tips based on my brief, but so far successful, experience pursuing and starting my content marketing career.


1. 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.

2. Don’t apply to hundreds of jobs

I've applied to about 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 related role. Anyone who advises 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. Prioritize your targets and the effort you invest in them. Track their careers pages. Follow their employees on Twitter. Read their blogs.

When you apply, write a resume and cover letter that's made for them. If you communicate one thing, show that you know them, and that you want to work for them. Like, really know, and really want.

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 show 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. 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. They don’t want to have to keep applying external motivation.

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 application 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. That doesn't make them wrong, and it doesn't mean you shouldn't explain them confidently; it just means you're figuring it out as go, 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. 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 keywords into every job search engine. (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.

I then built a content marketing career database. If I were to do it again, I'd make a spreadsheet, but I was scared of spreadsheets at the time, so I made a big bulleted list.

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, the title I saw, broadly what they did, their location, a link to their careers page, and any extra interesting details I may have seen.

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 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 skillsets and tech stacks in different companies. One "content marketing manager" might 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. 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 career path 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 followed 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 the niche you're pursuing and the valuable perspective you bring to that 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. Mine was on Medium, but I republished it here.

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.

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 get to great. You're always going to need inspiration from people that are in relatable positions, doing things you can 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 might 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 these tasks, the harder it will be to appreciate how hard they were to learn.

When you apply to the next job, you'll have all the material you need for a new resume, cover letter, and interview right in that journal. More importantly, you'll be able to look back on all your growth and feel confident about your future.

Track your successes and failures closer than your 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 an outsized effect.

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 most 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 is 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 that instinct 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 boss
  2. You risk only getting good at the job you have rather than the job you want

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'd be 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.

If you master the tasks assigned to you, you'll become the master of doing those tasks. That's all.

Some people, usually older, 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 how 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 (key performance indicator) was articles created, but I knew the KPI behind that was traffic. Instead of working as I was directed, I worked for the primary 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 educational 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. At the time, this was unthinkable. We couldn't compromise, and I lost the job. I worked 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 $32K 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 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 publisher. You have to do a lot of work to find a job that suits your spirit so well 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 difficult to carry out.

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 get "imposter syndrome," the sense that you're faking the value you offer and that 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 encourages your confidence. If you're confident, you grow through your incompetence. You can embrace it.

As you do 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 eventually 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 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.