How I Started Making a Living Writing in 60 Days

5 critical lessons from a CMO turned freelance content writer

Two months ago, when I lost my job as Chief Marketing Officer (CMO) for a tech startup, I set myself a new goal — creating my own content marketing business. And with just two months of severance pay in my pocket, I knew I needed to get busy if I wanted to keep the wolf from the door.

Now, with the severance pay running out, I can say I’ve already started making some money writing white papers, blogs, and marketing copy. Better still, I can pick and choose my projects and can work anywhere. Even southern Italy, if I so wish.

Although I’m just getting started writing for Medium, I’m nonetheless learning how it works, slowly gaining momentum in terms of views and followers.

Admittedly, I want immediate, meteoric success. Instead, I’m getting a chance to learn new things and meet new people, which is probably better in the long run.

Throughout my twenty-five-year career, I’ve taken pride in my work. Until now, however, I didn’t have much personal skin in the game. Instead, my ego was tied to my title and salary. If the companies I worked for didn’t meet their goals, I always had plenty of others to blame. Now, with nothing but my name on the door, the stakes are much higher. This time it is personal.

Yet now, ironically, with my ego on the line in ways it never was before, I’ve discovered that the more open and honest I am with people, even potential clients, the more they trust me. I learned a long time ago that nobody likes perfect people.

I’ve also learned that the best way to become truly successful is to help others succeed. Success, it turns out, is not a limited commodity or a zero-sum game. It’s there for the taking. For everyone.

In that spirit, I want to share what I’ve done in the hope that it helps you.

Here are some of the critical lessons.

Lesson 1: Ask for help

You would think that with more than 25 years of corporate marketing experience, building and promoting my own business would be easy for me. It isn’t.

It turns out; there’s a lot I don’t know, especially when it comes to hanging out a shingle. Namely, how do I create quality content and build the business when I have almost no budget?

The answer is, get creative and ask for lots of help.

While I was busy building my website and trying to gin up some business, I was also reaching out to my network. Using LinkedIn, Facebook, Instagram, and other platforms, I sent messages, emails, and texts to all sorts of people, just asking to chat. Nearly everyone agreed to meet me virtually, for what I call a “Zoom coffee.”

I didn’t go into these calls expecting business; that wasn’t my goal. Instead, my goal was simply to reconnect, catch up, and, most importantly, find out what they’ve been doing. People like it when you ask them what they’ve been doing.

In this regard, the most important thing I learned is that I’m not alone. Many people have had to rethink the work, as well as reframe some of the underlying narratives about life.

By going into these conversations with a sincere desire to learn, I’ve ended up rekindling some old friendships and even being introduced to some new people.

Without asking directly, when I told people what I’m doing now, I got a lot of support and encouragement. Many of them even said things like, “you should talk to so-and-so; she could use your help.”

A couple of dozen calls later, I had put together a robust support network. Many of these people are incredibly successful, experts in their own right. What’s more, they were more than happy to help me, in whatever way they can.

And in these conversations, I learned that the trick to asking for help is showing interest in others. In other words, you don’t need to ask, just talk to people. And listen.

Lesson 2: Demonstrate your value

If you know your work has value, don’t just tell people that it’s valuable. Prove it. Show them. In my case, I decided to write a few white papers for free, in exchange for case studies and testimonials.

I was confident that once they saw the results, they’d hire me to do more. At the same time, while researching and writing the first of these white papers, I got connected with two other companies in the same field. They both wanted to hire me outright.

Again, by simply speaking to and interviewing people in the field, I demonstrated my competence and acquired new business — without hammering people with emails.

Also, in some cases, I’ve entered into valuable barter agreements for free design and video help. Such quid pro quos provide immediate value and can lead to numerous referrals.

In one case, working with a consultant, I made a profit-sharing arrangement. Realizing she couldn’t pay me out of pocket, I agreed to let her pay me a percentage fee from any new business she gets from my work. Again, it’s about being creative.

Likewise, I’ve set aside a few hours each week to mentor emerging businesses and young entrepreneurs — for free. Why? Because being generous with my time and experience not only helps others, it also inspires generosity in them. Which often leads to even more paid opportunities.

The point is that good work is good work. In other words, the path to generating income as a writer is not always a straight line. Sometimes it takes a lot of patience. But show people what you can do for them and eventually, you’ll be rewarded tenfold.

Lesson 3: Always be curious

I am a naturally curious person. If you’re reading this story, I suspect you may be too. Curiosity, in my estimation, is not only one of the keys to good writing, but it’s also the key to better marketing.

As I said, the day I went into business for myself, I was no longer marketing someone else’s business. For the first time, I was selling myself. As such, I faced a steep new learning curve.

Without a team or much budget, I was faced with mastering new a whole new set of skills, platforms, and tools.

Despite having decades of marketing experience when I started down this road, I knew very little about building a following on Medium, Facebook groups, podcasts, and other channels.

Honestly, at times the process has been a little daunting. I continually need to remind myself that learning is its own reward. Not only that, by carefully documenting everything I learn along the way, but I can also repurpose what I’ve learned for resale later.

Just last week, I recorded a mentorship call in which I explained the difference between countering and dissolving objections, and, more importantly, why the latter is more effective. This week I’ll transcribe the conversation and turn it into a blog article for a paying client.

In the meantime, I’ve got other goals. One is to learn how to publish and sell ebooks and online courses. To that end, I’ve started researching and reading articles, as well as connecting with experts and joining groups.

And it turns out that there are groups for just about everything you can think of, and they’re full of helpful folks. For instance, even though Italy is closed to American travelers, I was able to join an expatriate group in southern Italy and start learning about what I hope will be my future home.

Lesson 4: Contribute to communities

One of my chief complaints about my fellow writers and artists generally is our selfishness. Too often we are so busy looking for affirmation and recognition that we forget that no one is in this alone.

To be sure, creative people spend a lot of time alone, but that’s not the same as going it alone. Trying to do everything alone is a recipe for failure in any endeavor, especially creative ones.

So, the next time you join a group, try to be a good member first, instead of seeking validation (or clients).

Human connections, even online ones, are enriching and inspiring. By participating in communities, we can cultivate new relationships and, in turn, create more opportunities.

Lesson 5: Measure your successes

I’m still a long way from earning the salary that was mine as a full-time marketing executive. Nonetheless, I’m feeling happier and more fulfilled.

Which dovetails with my discovery that when it comes to building your own business, revenue is only one measurement of success. Equally important are other, less tangible mile markers, including product-market validation, effective time management, and productivity, as well as physical well being.

At the end of each day, I try to add up all my accomplishments, no matter how small they seem, and give myself credit for a job well done. Likewise, I surround myself with people who like me and encourage me. In turn, I try to do the same for them.

I call it “the ROI of being nice.”

Even though 2020 may be on the lean side in purely financial terms, I’ll get by just fine. Moreover, it’s already been a very successful year in terms of learning and personal growth.

Ultimately, I find I’m happier when I define success by what it means to me. And measure it on my terms.

By next summer, I plan to be working from Italy. I will keep you posted on my progress.

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Sean Smith is Founder and Chief Iconoclast at Virtù b2b.