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I wrote previously about some tips for Freelancers working with small business, and while that’s all relevant today, I still see freelancers missing the mark when they speak to me and offer me their services.  Likewise, I hear the frustration that they’ve worked with other small business.

One thing that I think has continued to negatively affect the way that our two groups can work together, is that we’re too often looking for something that’s a perfect fit, instead of being more flexible and offering a broader set of services. 

So, as you might expect, I see some ways to bridge the gap.

I’m going to make some suggestions for how to bridge the gap and as a freelancer, to drum up some repeat business, even when a small business isn’t actively looking for the exact thing that you’re selling.

If You’re a Graphic Designer

I think that graphic design might be the most popular work currently on Upwork.  But the real question is, how can someone that is a graphic designer continue to pitch what they do when a company isn’t actively looking for a graphic designer?

If You’re a Graphic Designer: Offer Keyword Researched Content (No, seriously):

One thing I think the graphic design freelancer could do, not only could they provide an agreed-upon piece of artwork, like the ones they are already submitting, but offer fundamental question and answer articles based on keyword research. 

This is something that I struggled with for some time.  I was creating blog content for quite some time.  Like hundreds of blogs.  Often, according to others within the industry that I asked about it, they thought it was interesting and insightful blog content. So yeah, people within the wine industry LOVED my material.

Exactly 0 consumers were looking for it.

What would have helped?  If one of the graphic design freelancers I hired over the years, had said, “look I checked into your niche” and “there are 4k people searching for this every month”.  “Let me build it and let’s get those people onto your site.”

I would have said yes, without question, and without thinking about it for long. A graphic designer runs one of the most successful wine blogs out there, so someone could also pitch me additions for some of my cornerstone content that already exists.

If You’re a Writer

Okay, so most Upwork postings are for people willing and able to commit to writing a blog.  That’s cool.

But, what happens after you complete that specific assignment?

First, a bit of background, this is a big one. I accept guest posts on my site just like (just like Nissar does here, at Career Metis and I’m sure he can talk to the struggle that it often entails more than I can) because I legitimately want people to offer their perspectives on the wine industry, what I get is a lot of generic spam of course.  There are a few folks that do reach out and provide an article that works for me and my readership, for some time I found myself wishing that there were more opportunities to help writers who were doing a good job.

What would I hire for immediately?  Someone with a list of sites that they could guest blog on, on my behalf.  I’m not talking about a list of sites where you google “Accept guest posts” and then submit, but instead an actual list of curated sites that only accept real guest posts.

Of course, there’s an incredible amount of link equity to be gained from that type of list, but there’s a legitimate amount of PR value to be found as well. Both of those draws me to the guest post (admittedly like this one) but someone else that had a curated list, would be golden and could gain quite a bit of side-business from me.

Freelancers - Freelancing Website to Write - Freelance career- Routes to Freelancing Success-Freelance writer-Freelancer

Customer Service Specialists

Often, I see that customer service specialists are advertising or looking for jobs as freelancers, tend to focus on delivering service in one way or another.  Some are available to take calls.  Others will respond to emails.  Still others, live chat.

Given that most of my customer service tasks involve logging into my software system to look up information for wine shipments (like tracking numbers) someone who provided all of the above types of service would be a better fit, especially if they only charged me per action, or per their time.

In my opinion, a customer service freelancer can provide value and create long-term relationships, by branching out and offering their services via more than one medium.

Lastly, 1 Job to Not Offer Me


Seriously, this happens every so often with a freelancer.  The offer is typically something like $10 a minute to transcribe my video blog entries.  Freelancers have to understand that if you’re pitching something outside of the mainstream, small business owners are going to check.  Rev and similar online transcribers, charge something akin to $1 a minute for their services.  They’re fast, they’re efficient, and really, these transcription marketplaces don’t leave a lot of space for an individual to provide the same level of service, at the same cost.

In Conclusion

We often tell a freelancer and small business owners to put themselves in each other’s shoes to create better, more lasting relationships.  That’s true, of course. But, we also need to find ways to help each other, without being specifically asked for help. For freelancers, that’s helping small business owners with tasks that will grow their business, even if they don’t know that those tasks need completing.

For small business owners, it’s also helping freelancers to create ongoing streams of income, so they aren’t spending so much of their valuable time looking for short-term assignments. I hope this, as well as my other writing on CareerMetis, helps to bridge the gap a bit.


Written By
Mark Aselstine is the owner of the Uncorked Ventures Wine Club an online business based in the San Francisco Bay Area. A father, husband and lover of all things politics, sports and entrepreneurship you’ll often find Mark on Twitter, arguing about pretty much anything other than wine.

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