Lessons Learned From My First 12 Months of Freelancing

9 min read
By: Maddy Osman

I’ve been planning this post for many months – over a year, in fact! It’s finally the right time to share the story of my first 12 months of freelancing. Coincidentally, LinkedIn Profinder is also running a small business contest that invites small business owners to share their unique stories, and I think mine is something you’ll want to read.

For those landing on my blog for the first time, my name is Maddy Osman, and my brand is “The Blogsmith.” After months of brainstorming, it seemed like the perfect fit for my personality, leveraging my love of street art to show people that their content can be effective and fun, while still being professional. My clients range from lifestyle brands to tourism agencies, marketing agencies, and more. But my passion is writing about digital marketing, and breaking down complex topics.

After investing a lot of time and effort into learning about SEO (originally to promote my passion project/blog Chicago Cheap Ass), I help my clients create content that is easily found by people specifically seeking it out. Once searchers click through to learn more, my content is easy to read and engaging. Thanks to my marketing background, the content I write always has a conversion factor so that the brands I work for can create short and long term prospects.

The impact my business has had for my customers is obvious once you start to look at the stats. Here’s an email from one of my favorite clients, ParkWhiz:

In another case of high-impact, a series of articles I wrote (on topics of my choosing) for client BLR’s Sales & Marketing Daily Advisor were repurposed as a marketing asset to drive new email subscribers. These two instances represent examples of client wins that happened in just the past month!

LinkedIn has always been a very large part of my personal branding strategy. I attend networking events on a regular basis and try hard to be good at following up with the people I meet. At the end of every day, I make sure to use LinkedIn to connect with people not currently in my network (Rapportive is another good tool for connecting directly through email).

By consistently posting relevant content via LinkedIn status updates (client wins, relevant industry articles, local involvements, and more), I stay top of mind with my large business network. At one point in time, my profile was in the top 1% most viewed on the platform! Anyone who knows me knows that I take LinkedIn very seriously – enough to write an article about the most common mistakes people make on LinkedIn for one client, and how to write a good LinkedIn summary for another.

LinkedIn ProFinder represents a great new opportunity for creating business leads. I’ve experimented with it and have had many great conversations, and a freelance friend of mine recently closed a lead with a company paying him $75/hour – no easy task for contract work! I can’t wait to see how this new platform evolves as more companies and individuals use it to hire freelance talent. We certainly deserve better than typically high-fee, low-paying platforms that freelancers are often directed to, especially when they’re just starting out.

Now that you’ve had a chance to see the impact my business has had on my customers, I’d like to share a personal story of my first 12 months of freelancing. Here’s how my business has impacted my life, with lessons learned for others interested in taking the leap.

Month 1: October

Making the jump to freelancing full-time is a lot easier when you have enough client work to at least pay your bare-minimum bills. But even with the promise of some work, nothing is set in stone. Corporate jobs with benefits seem so much more secure, and in many ways, they are. If you’re considering making the jump to freelance, check out the Month-by-Month Guide to Starting a Freelance Business that I wrote for Sophie Lizard’s blog – it digs deep into both the things I did and wish I had done before quitting my job!


Besides the financial considerations, there’s also something to be said about losing out on office culture. It can be annoying to get up early and look presentable, then commute in traffic or crowded public transportation – I won’t argue that! But being able to work in your PJs and sleep in a little longer doesn’t make up for a lack of conversation and company. Although I’m very good about getting out of my house and regularly attending networking events, I miss consistent interactions and commiserations with my favorite coworkers, and it hit me hard after my first month on my own.


My first month freelancing was one part “OMG I’m really doing this!” excitement and another part “OMG what happens if I fail?” I think most freelancers go through the same range of emotions when just getting started.

Month 2: November

My second month was full of change. In an interesting turn of events, the client who helped me cover my bare minimum bills and I parted ways. It could have brought about an early end to my fledgling freelance career, but another one of my clients really ramped up the work they assigned to me. In the end, it all worked out. Though my main first client and I were not meant to work together in this capacity, we’re still good friends and I consider him to be my freelance mentor. Sometimes good things fall apart so better things come together – I’ve always believed that.

Month 3: December

I was grateful for the work from my new main client, but I was frustrated with the way it was going. Though there was some structure to our working relationship, I felt like I was always on call, and that I was powering someone else’s dream (instead of building my own company/brand).

As someone with a major case of #BusinessMajorProblems, I craved structure and the ability to plan ahead. After all, the main perk of freelancing for me was supposed to be the flexibility. I know that if I continued working with this client, it would be damn near impossible to take vacations without a significant amount of stress. So by the end of this month (despite the busy holidays!), I was working hard to drum up new business that would allow me to live my dreams.

Month 4: January

January was probably one of my worst months as far as business (and getting paid!) was concerned. With all of my contacts on vacation, it was hard to get new assignments. There’s really no reason to be frequenting your email inbox when you’re off the clock! #CorporatePerks


Instead of letting it get me down, I used the time I would have been completing projects to instead work on building my personal brand. By the end of the month, it was paying off in the form of inbound leads through my professional social media channels (LinkedIn and Twitter), on top of referrals from people in my network.

Month 5: February

After realizing how effective my personal branding efforts could be, I made a point to invest more time and energy into them during the month of February. This effort centered mostly around guest posting on high authority websites (like this piece I wrote for Search Engine Journal) in my industry, and being featured on podcast interviews to share my story and convey my expertise (like this one for Brand Driven Digital). Especially in terms of my guest posting efforts, I’ve created powerful portfolio pieces that I still use when pitching new clients, today.

Month 6: March

For me, March was all about being more efficient. When running a service-based business, there’s only so much you can do before you run out of hours in a day. Besides time constraints, you also get to a point when you’re overwhelmed and low on energy. So during the month of March, I started thinking about what I could outsource, if anything, without compromising on quality. I also committed to using new tools to help with organization and keeping track of client assignments. Once I was feeling good about my new processes and plans, I gave myself a raise. From this month on, I vowed to myself that I would never charge less than I knew I was worth. I wish I would have had this level of confidence months ago!

As a nod to the fact that I was missing having coworkers, I also decided to give coworking a try this month. In Chicago, Deskpass makes it possible to try multiple coworking spaces at a very affordable price. From March til my eventual move in November of this year (2016), I gave many different coworking spaces a try. Getting out of my house (and away from Netflix) was excellent for productivity! If you’re local to Chicago (or going there for business), check out my article on coworking spaces for Choose Chicago.

Month 7: April

It wasn’t until month 7 that I felt comfortable enough with the processes I put into place, and the clients I had, to actually take a vacation. Before freelancing, I think I took vacations for granted, but never again. I have to do so much work ahead of leaving, and require a wifi connection once away in case it becomes necessary to put out any fires. As long as I’m freelancing (which I hope is forever!), I’ll never be able to completely relax during my downtime. It’s the tradeoff a person has to deal with for a non-traditional job situation!

Besides taking a much-needed break, I made the most out of the remainder of the month. I began picking up speaking engagements (like WordCamp Chicago!), won well-known Freelance Writer Sophie Lizard’s Pitchfest competition (my winning entry is linked at the beginning of this post), and picked up some unexpected consulting work. Because I’m always trying to be more efficient, I spent several days reducing my email inbox from probably ten thousand messages (if only I was kidding), to organized labels and inbox zero! I highly recommend an inbox cleanse if you’re starting to miss important messages.

Month 8: May

In May, I picked up 4 more speaking events and expanded my influence and expertise in Chicago, while practicing my ability to talk in front of large groups of people without sounding like an idiot (easier said than done). I also picked up my first event live tweeting client, launching a service I have a lot of passion for. May was truly a month of opportunity, both in terms of building my personal brand, and making more money!

Month 9: June

June marked the addition of a few new business expenses, but thankfully, also many new efficiencies! I pulled the plug on finally hiring an assistant (she’s a lifesaver), and also signed a two-year contract for an unlimited/portable wifi hotspot (it’s awesome, by the way). I also started working with a few agencies both on their client projects, and on their agency blogs as a contributor (like client Mabbly).

Month 10: July

After hiring an assistant, I had to learn how to delegate and manage. The book Virtual Freedom was an essential resource for learning how to effectively work with someone in a different place. During this month, I also created more processes for my business, like a new client intake form to learn as much about the companies I’m helping with blogging and social media (or web design) as possible before getting started. One of the highlights of July was when AT&T hired me to write a number of small business articles for their Small Business Circle portal.

Month 11: August

It was near the end of my first 12 months of freelancing that I started picking up some truly amazing clients. I have a lot of clients I’ve been working with since the beginning of full-time freelancing that are amazing, but I’ve always had my eye on writing for big brands. A freelancer friend connected me with a unicorn client – Adobe! I’m happy to say that they are now a client, and my first article was about the role of UI/UX in solving self-driving car challenges. Before closing out the subject, it’s important to talk about creating a freelance squad. Even though my Adobe contact handles similar client work, she helped me expand my own career. Freelancers need to stick together – there’s more than enough work for all of us! Think of freelancers as your coworkers, not your competition.

August was an awesome month for business, and really felt like the culmination of all the time and energy invested into making freelancing work prior to this point. Thanks to a website redesign and increased efforts on LinkedIn, Twitter, and Facebook, I started getting 1-2 inbound leads each day! I also had two paid speaking gigs this month. Another highlight of August was getting hired by Nick Westergaard to help with his social media conference, Social Brand Forum. Leading up to the conference, I helped create social content, blog posts, and assisted with live tweeting during the event.

During this month, I was privileged to attend an awesome Chicago conference – Content Jam.

Month 12: September

In September I attended Social Brand Forum and made a lot of new friends while growing my network. I started using the Hubspot Sales CRM to manage prospects and client relationships. I also began playing with the Pomodoro Method (this tomato timer is as genius as it is simple) to work on my ability to focus and knock out client work in a more efficient manner.

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Final Thoughts: Lessons Learned From My First 12 Months of Freelancing

I’m writing this in November, which means I’m officially past my first 12 months of freelancing.
There have been so many ups and so many downs, but when it comes down to it – I wouldn’t change a thing. Everything I’ve been through has been a learning experience.
I can’t wait to see what the next year of freelancing brings.

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Maddy Osman

The Blogsmith

Maddy Osman is the author of Writing for Humans and Robots: The New Rules of Content Style. She's a digital native with a decade-long devotion to creating engaging, accessible, and relevant content. Her efforts have earned her a spot in BuzzSumo’s Top 100 Content Marketers and The Write Life’s 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.

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