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Freelancer Spotlight: Maddy Osman from The Blogsmith

Maddy Osman is a true pro and people connector. And one of the few freelancers I’ve met who doesn’t dread networking events. 😉

In fact, Maddy helps organize networking events in Chicago, where she is based. And today, Maddy agreed to answer our Freelancer Spotlight questions and let me tell you… she was fast!

Here are her insights into working for yourself and how to raise your rates as a freelancer.

What do you do and how long have you been in business?

I’ve been freelancing full-time for about a year, but part-time for over six years. Before going full-time with freelancing, I’d been a brand ambassador for Sony and Zipcar, did outbound sales for Groupon and a small digital agency. I also worked as a web designer my entire time in college. My eclectic past has taught me the various skills I needed to be good at what I do now.

For my business, I write SEO copy (blogging and other web content) primarily for digital marketing agencies and individual thought leaders.

How did you start freelancing?

When I was designing websites back in college, my boss recommended me to his friend as someone who could help put together a nice website. From that point forward, I almost always had some kind of side gig, including writing and social media jobs.

While I was stuck in sales, I met Brent Jones, who encouraged me to go after a freelance career. He helped my transition with work and by sharing lessons learned from his experience. Freelancing was really hard in the beginning, but every month it got a little easier as I created structure and processes within my business.

(Gina’s Tip: Brent Jones is a great guy who’s making a killing online. Check out this podcast episode in which Brent and I chatted about how to transition into freelancing.)

What has been the most challenging part of solopreneurship so far?

Each month is a new challenge when you’re just getting started, but my current biggest challenge is finding time to do everything I need to do.

When you first get started, it’s unlikely that your client roster is full. You have free time to pursue new clients and focus on branding efforts. Once you have a full book of business, those marketing activities fall a bit to the wayside.

I’m in the process of hiring a full-time virtual assistant to help me with administrative tasks, research and other simple tasks I don’t need to complete on my own. I’m hoping this will give me time to refocus on personal branding efforts and other activities I enjoy with growing my business!

Freelancer Spotlight_ Maddy Osman on How Freelancers Can Raise Their RatesDid you ever want to quit or give up?

There are days where I definitely want to curl up in bed and leave things until the next day, but I always push through and give work my all until it’s done!

I can’t see myself quitting – I love the flexibility that freelancing has allowed me. I hate asking for permission, like when trying to schedule vacation days. Life is too short to live every day by someone else’s rules.

And as long as my clients are happy, I take personal time to live a balanced life.

What task in your own business would you like to do more of?

Blogging for my own brands: ChicagoCheapAss.com and The-Blogsmith.com. I also love attending networking events and try to fit in as many as I can, as they’re great places to meet potential clients and collaborators.

My portfolio website is in desperate need of a facelift. And I have so many ideas, but such limited time to act on them.

What are some big successes you’ve had recently?

I’m starting to be recognized at some of the networking events I regularly attend, by people I’ve never actually met in person before.

And I’m starting to get a lot of inbound leads for jobs, coaching requests and even training workshops. Sometimes these inquiries lead me to new service offering considerations I hadn’t thought of before.

Each month I feel more and more convinced that I’m doing the right thing for me, which is reinforced by the fact that I can more than pay my bills.

I’m starting to respect my time and my skills more and more – raising my prices on a regular basis!

What’s your strategy for raising prices?

I wait until I become indispensable.

At this point, the client is probably asking for work past the scope of what we originally discussed. So I tell them I’m happy to do it, but my time is becoming more valuable and I have to charge accordingly. I don’t do big jumps, just incremental changes.

So far, none of my existing clients have stopped working with me because of this and I’ve made more money off those contracts because I wasn’t afraid to ask!

What are some specific strategies, tactics or pieces of advice that helped you grow?

In general, I like learning from and talking with people who are successful who have had some tough breaks. It makes me feel like even when I deal with setbacks, they’re just stepping stones on the way to the next thing.

A lot of success is getting in the right mindset.

(Gina: I like this attitude, Maddy. I shared some of the setbacks I had mid-summer in this income report.)

Never underestimate the power of your network.

Connect with everyone you meet on LinkedIn, proactively grow your Twitter, go to local networking events and conferences. Tell people what you do and that you love referrals. Try to grow your network and give help or advice before asking for anything in return.

What are you most excited about for your business next?

I have two partners for two projects that are vaguely related to my main business. I’m excited to kick those things off and see where they take me! I know that offering services can only take me so far, which is why I’m attempting to diversify my income.

Maddy OsmanMaddy Osman is a content marketer and the founder of The Blogsmith and Chicago Cheap Ass. You can connect with Maddy on Twitter or at one of the networking events that she co-organizes in Chicago. 

What about you? Do you have a love-hate relationship with networking events, or are you a networking pro just like Maddy?

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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