How to Score Paying Clients for Your Side Hustle When You’re Short on Experience
May 2014

How to Score Paying Clients for Your Side Hustle When You’re Short on Experience

Welcome back to the Side Hustle Shuffle series! In the introductory post last week, we discussed the what and why of side hustles. Today, we’re diving into the how. Read on to learn how you really can make extra money on the side by picking up paying clients – even when you’re short on experience and just starting out.

We’re going to be addressing what many people view as the most intimidating part of starting a side hustle: actually being able to make extra money on the side. Because doing that requires picking up paying clients, something we’ve been told is hard to do when you lack experience.

Today, we’re calling BS on that nonsense. Everyone starts somewhere, and you won’t jump into a new side hustle with years of experience under your belt (most of the time, anyway). That doesn’t mean you can’t score paying clients and grow your gigs from the very beginning.

But first, we need to do a quick evaluation of our original side hustle idea.

Double Check to Make Sure You Have Access to Paying Clients

Remember how we talked about the fact that your side hustle could pretty much be anything? This is absolutely true, but some side hustles are going to be easier to get off the ground than others.

The biggest obstacle you may face is not a lack of experience. It’s gaining access to your ideal client.

If you love animals, for example, and you want to start a pet-sitting business, you’re going to have a hard time picking up your first few paying clients if you don’t know a single person in your network that keeps pets and would like someone to take care of them while they’re on vacation.

That’s not to say you won’t be able to make this work. But you need to come up with a plan to gain legitimate access to the people you could serve – and hanging around the front doors of the local pet store and harassing shoppers by shoving a flyer you made in Microsoft Publisher in their faces is not a great option.

Yes, people in your area may need pet-sitters. But if you don’t have any experience and you have no way to showcase what you can do for them, you’re going to have trouble convincing strangers to hire you and utilize your services.

If you’re working in “the real world” but have no ability to connect with your ideal client, establish trust, and grab your first paying gig, it’s going to be hard to get started.

Likewise, if you’re interested in working in the digital space online, but don’t want to have any sort of public web presence with which to establish a connection with people who need what you have to offer, it’s going to be really difficult to convince a perfect stranger that you’re the right person for the job.

So quickly evaluate your chosen side hustle. If you’re working in face-to-face situations but you don’t know a single person who could benefit from what you’re offering, you’ll need to come up with a creative solution to overcome this first problem. Same goes for wanting to do virtual work but not wanting to build an online platform.

You need to have some sort of access to your ideal clients. If you can’t think of a way to reach them in a way you’re comfortable with, it’s likely that you need to go through a fresh iteration of your original side hustle idea.

Creating Effective Channels of Communication and Connection

But, thankfully, the reality is that most of us have some sort of access to our ideal client. At the very least, we have the ability to create a channel of communication if we’re dedicated to the idea.

For example, if we want to get started with virtual work but have never done anything like it in the past, we can simply set up a simple website and perhaps a blog. From there, we can grow our online platforms into channels we can utilize to gain access to and acknowledgement from potential clients.

Similarly, if we want to pet-sit but we know exactly zero acquaintances that own pets, we can get started by volunteering at an animal shelter and building a new network of animal-centric friends who will need pet-sitters (and know of others who will need pet-sitters).

This is a long way of saying that what we think of as big challenges when we’re starting with side hustles are actually 100% manageable. Keep in mind, gaining access to your clients is actually far more difficult than scoring paying clients when you’re short on experience.

If you can get in front of an ideal client, you’re halfway to being able to make extra money with your side hustle.

Say it with me, friends: you can score paying clients even when you’re short on experience.

Let’s explore how to make it happen.

How Do You Start When You Have No Experience?

We all know we need experience to gain work, but we need the work to gain the experience. Right?

Heck no! If this were true, we’d all be endlessly stuck in a loop of work and side hustle frustration. What is true is that we all start somewhere, and the beginning of the journey may look radically different than the end. But the fact remains: we all get started somewhere.

Let’s return to our pet-sitting example, where we danced around the solution to what looks like a catch-22. If you want to pet-sit, but have absolutely no experience in doing so, you need to establish some sort of proof that you can do this.

That might mean offering to help care for a pet that your friend, family member, or coworker owns. You may need to volunteer your time or efforts, but do so in exchange for a review, testimonial, or recommendation.

You may have to start out doing some work for free in order to collect the first few pieces you can use for your portfolio or reference book.

This doesn’t mean you should do everything for free – and it doesn’t mean you shouldn’t be compensated in some way. When you’re just starting out, exposure and word-of-mouth marketing have some serious value.

If you do some work or provide a service or product to someone within your network, make sure you get something of value to your budding side hustle in return.

Just like that, you have a way to start even with zero experience.

Pick up 2 unpaid gigs, even if they’re just for a friend or family member, and knock them out of the park. Then collect a great testimonial or use those super-impressed people as a referral when you apply for gig #3: one that pays.

Make Extra Money and Secure Paying Clients by Working for Yourself

You don’t even have to work for someone else. If you’re trying to establish a digital side hustle you have the option of producing content and samples for your own site or blog.

That’s precisely how I got started with my own side hustle. In fact, here’s a basic outline of the steps I personally followed:

  • Started Common Sense Millennial in late July, 2013.
  • Wrote lots of posts that no one read. Found my voice and started writing better stuff.
  • Established a social media presence and started building connections with fellow bloggers and others in the industry I was interested in.
  • Read about how people were making a living a full-time bloggers. Reached out to several other bloggers to inquire about staff writing. Got turned down every single time.
  • Gained confidence by using my blog as my resume when applying for some content writing jobs. Pay was low but it was a start!
  • Went back to fellow bloggers. No’s all around again.
  • Decided to branch out and tried contacting others in the financial industry. Finally, success at pitching myself!
  • Word-of-mouth marketing took off and my side hustle grew exponentially after this point (including finally landing contributor spots with two awesome financial blogs: L Bee and the Money Tree and Your PF Pro)

When you “work for yourself,” or pursue your own thing – like a blog, website, or other project – you’re essentially creating your own experience. You can then use this to pitch your services to potential clients or when applying for a gig somewhere.

More Actionable Steps to Take If You’re Looking to Score Clients with Little to No Experience

Yeah, yeah, but what if I already have a blog or have been doing work for free? Now what?

Great question. If you’ve already established your own blog or have picked up a handful of clients for your side hustle, you’re off to a great start – but you’re likely wondering how to keep that momentum going.

On the last Side Hustle Shuffle post, Connie of Savvy with Saving asked about finding new clients and getting your name out there when you’re looking to grow your side hustle. E.M. of Journey to Saving had a related question, and wanted to know how to continue building on experience when just starting out with a side hustle.

Here are five actionable tips to help you score (more) paying clients and how to continue building your experience if you’ve already been doing some work for free, either on your own projects or for someone else.

Ask. The best way to pick up more clients is to put it out there that you’re actually looking to expand. You never know who has been thinking about hiring on some part-time help, but simply had no idea who to turn to.

Create a blog post explaining what you do and share that you’re looking to pick up new clients. Use social media to share a post about the kind of work you’re looking for. Turn to your network and ask if they know of anyone who could use your skill set.

Be proactive. One of my absolute best clients was one that I picked up because I sent an email asking if she’d like some help. While I initially pitched writing services, after we discussed her needs I ended up working for her as a content manager – even though I had never worked for someone as a content manager before.

It didn’t matter that I didn’t have that job title on my resume. It was much more important that I had the skills necessary to do the job and with my first view small assignments I completed for her, I proved I was capable of being a valuable asset to her business. So be proactive. And on that note…

Don’t fear the cold-call email. I know. It’s scary, it can make you feel sleezy, and it certainly seems like a big fat invitation to face a whole lot of rejection. But if you’re going to be a real hustler, a go-getter that makes their own fortune – and experience – you need to get over your fear of being the one to initiate contact.

Gather a list of people you sincerely believe you could help in some way. And then email them. The secret to creating a cold-call email that doesn’t piss people off is to be genuine, sincere, and honest.

Open with a greeting. Explain that you’ve been a fan of what they do (and point out something specific about them that you appreciate or admire, to prove that you talk the talk and walk the walk). Then share how you’re looking to expand your part-time work, and you’re interested in helping out if there’s an opportunity to do so.

And always remember your manners. That means asking about how the other person has been and saying please and thank you.

Create passive channels. Yes, you should take the initiative to pitch ideas or services to clients – but you should also have some sort of passive channel that people can find on their own that tells them about what you do and how to get in touch with you.

Most people do this via a “hire me” page somewhere on their site or social media accounts (mine actually links out to a completely separate site). You never know who might stumble across your corner of the web and be interested in working with you, so it’s smart to have an easy to access and understand resource for those who might just ask if they can be your next paying clients.

Engage in value-driven networking. When I started side hustling, networking was a dirty word (much like cold calling). It conjured images of people throwing business cards at each other. I felt like networking was ridiculous and a waste of time because what was the point of trying to connect with a group of people who only wanted to get and not give?

The good news is that networking doesn’t have to be this way. What I mean when I say “value-driven networking” is that you should be eager to make new connections and then immediately provide that person with some kind of value.

In other words, network with giving in mind – not getting. It can be as simple as providing a quick tidbit of advice or as generous as offering to write a free blog post. When you connect with someone, you should be thinking something along the lines of, “how can I help this person in a meaningful way now that we’re aware of each other?”

Keep things sincere. You should have no expectation of receiving something in return for a small gesture that you give to someone else. But rest assured, in the business world, what comes around goes around (even for side hustlers).

Also, keep things relevant. Identify who the industry leaders are in your field. Follow them on Twitter and @mention them or engage in a conversation they’ve started. Read the blogs of people you’d love to work with, comment on their posts, and send them an email with a helpful suggestion if they mention they’re struggling with a problem or situation.

Diversify your hunting grounds. Finally, if you’ve picked up a few clients but you’re looking to gain more, consider going a little outside your comfort zone.

If you’ve had luck finding a handful of gigs via one venue, search for another.

For writers, Problogger is a big-time job board that everyone is trolling. But it’s not the only source for job leads out there. Hunt around and find new places to look for postings, or try emailing a different set of potential clients next time around.

You may feel like you’re stuck in a rut when it comes to growing your side hustle or acquiring new clients. But it may be that you’re just fishing in a teeny tiny pond that everyone and their brother is trying to fish in, too.

Expand your horizons and try something new. Be sure to try something new on a regular basis and more than once, mind you, if you want to eventually have success. Rarely do things work out for us the very first time we give them a go. Stick with it. You’ve got this.

Stay Persistent and Consistent

If you do all of these things, consistently and over time, you will score paying clients.

Even if you’re just starting out. Even if you’re short on experience.

Hit on all these tactics and keep at it, and you will see your efforts pay off.

What other questions do you have about scoring paying clients even when you lack extensive experience? Did you find new strategies here, or are you still feeling uncertain of how to get started?

If you need additional tips or feel like your questions weren’t adequately answered, I encourage you to speak up in the comments. The Side Hustle Shuffle series is meant to open a two-way dialogue, so don’t be shy!

Once you’ve left a question or two, it’s time to get back out there and put these ideas into action.

And keep up that hustle!

See other posts in this series:

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Anne @ Unique Gifter

Nice write up Kali. I like how you keep reiterating that you can create the network you need, if you don’t have it already. I ended up with some writing side hustles from my network and from social media, so far they’ve been great!

    Kali Hawlk

    Thanks Anne! I appreciate it. I think your network is by far the most critical piece of the puzzle – but the good news is you absolutely can build one from scratch :)


Great advice as usual! I agree with Anne – I liked the points about going out and finding the people you can provide your service to, even if you think you have none. I also liked the timeline you provided for your own success. As much as I try and comment everywhere, I am horrible with social media! I am barely into it for my own personal use, but I see the value it holds for networking and connecting with other bloggers. I think it’s time for me to start engaging more on those platforms. Also, I absolutely love your portfolio page.

    Kali Hawlk

    You always impress the heck outta me with how much you comment, E.M.! That is one thing I wish I had more time for – I read lots of blogs, but don’t leave a thoughtful comment as much as I want to. I would definitely spend some time on social media, as well, though. I think that probably holds even more value than commenting once you develop that recognition/relationship through sharing your thoughts on blog posts. It’s a quick and easy way to connect and expand your network.

    PS – Thanks for the kind words about my portfolio website! I feel like it’s still a work in progress but hey, it’s functional and serves its purpose. I think prettying it up is going to be a never-ending process!

Broke Millennial

What a comprehensive overview! I’m with you on needing to put some content out there for free (ie: starting a blog). It helps establish a body of work and gives you credibility. I’ve found Twitter to be my greatest asset in the hunt for side hustle gigs (other than cold emailing of course).

    Kali Hawlk

    You’re definitely one of my social media heroes :) Twitter, LinkedIn, and things like private Facebook communities have all been instrumental in helping me build a profitable side hustle. Although they would have been difficult to leverage had I not had this blog first. Blogging is such a FUN way to build reputation, experience, and credibility, so I’d definitely recommend everyone give it a shot as one of the best ways to “work for free.”

Melanie@Dear Debt

What a very helpful list, Kali! I’m excited about this series, as I love side hustling! I really enjoyed your points on networking being more about giving than getting.

    Kali Hawlk

    Thanks Melanie! I think that’s probably one of the biggest lessons I’ve learned – it’s always about adding value, ESPECIALLY when you’re trying to navigate something that traditionally is all about getting.


Great article Kali. Congrats on having the guts to push through the hard moments when all you hear is ‘no, no, no’.

Thats takes real grit, and its grit more than anything that leads to long term success.

Thank about it. You havn’t been blogging for a full year yet and your becoming a success online. That is truly awesome!

Long Term Brian

    Kali Hawlk

    Thanks Brian! That means a lot to me – I consider being tenacious and having some guts as a couple of my best assets, so your comment is a true compliment in my eyes :)

Poor Student

Great tips. This is something that I’ve been wondering as well, I like how you mentioned practical examples on how to do it :) I’m wondering though, did you also advertise on freelancing websites like elance, odesk, guru, etc? Or did you find prospective contractors by emailing them directly?

    Kali Hawlk

    Good question! I haven’t done a bit of advertising, and I’ve never used oDesk or Guru. I have a profile on Elance, but only because a previous client based overseas wanted to distribute payments via the site. I’ve never actually actively looked for work via Elance — to be completely honest, I feel like it’s a huge waste of time and not worth the frustration.

    I think far better use of your time, if you have time and can be patient, is to build your own platforms from which to work. This means blogging, networking, and getting on social media. I’ve used Problogger and Blogging Pro to find a few gigs, but my absolute best clients have come through me pitching my services directly or word-of-mouth and referrals.

JRod from

It’s amazing how working for yourself for free can land you paying clients. Your series of events is just about how it worked out for me. Thanks for sharing these great tips for the new comers!

    Kali Hawlk

    That’s awesome! I’m glad to see that process does work for more than just me 😀 And I agree, it really is incredible to see the return on investment when you do a bit of work for YOURSELF even if it’s unpaid. Our personal projects can lead to some great things, which is why we should always be open to pursuing them.


Such a great post, Kali! I’ve been following your blog since last fall and it’s been incredible to see you transition so quickly. You’re nailing it and I really appreciate you sharing your journey with us! Hopefully I can pick up a few pointers :) Keep up the great work!

    Kali Hawlk

    Thanks, Charlotte! I really appreciate that – your comment made my day. I’m still amazed things have zipped along so quickly. I think it just goes to show what can happen when you basically will something into being 😉

Newlyweds on a Budget

Great post Kali!! Full of so many informative tips that are right on target

    Kali Hawlk

    Thanks! I appreciate the kind words!


Hi Kali! I’ve been a silent lurker here on your blog and this has really inspired me to push forth and be more proactive about building my blogging side hustle. I’ve tried oDesk before and got paid peanuts for all the hardwork I did. I guess, coming from a third world country, clients get the impression that they can just pay me cents when I know fully well that I am worth more than that. I also have an Elance account but I haven’t actually bid for any jobs. I find that they ask for too much and pay too little given the quality of writing they require. Twitter is a great way to network. I’m still figuring out how to go about networking with LinkedIn for my blog.

Keep the side hustle posts coming! :)


This is uber helpful information! I’m going to be sharing it with a friend who is caught in the no work/no experience cycle right now.


Hi Kali- I really enjoyed your write up about finding new clients, especially since it’s been something I have been struggling with lately. I am starting a personal training/Celiac consulting business and am having a hard time finding new clients. I am not sure if posting on other related social media sites is a good idea because they may see me as competition. Do you have any advice for me? Thank you! Kelly

    Kali Hawlk

    Hi Kelly — thanks for the comment! That’s really exciting about your new biz. I think my biggest piece of advice would be to embrace your competition, and not worry if other people see you that way. If you’re running a digital business, the pie is pretty much infinite. This means your “competition” may be your best source of great collaborators!

    That being said, I wouldn’t make posts that are spammy or self-promotional. You should engage within your community and strive to add value wherever you can — people will appreciate that you’re being real, genuine, and interested in helping others rather than promoting yourself. When you put people first, sales follow naturally.

    Don’t be afraid to put yourself out there. It’s the only way to grab those new clients you want. But do it in a way that puts THEM first. Remember, you’re there to help others and that should help you craft your message to the world!

    Let me know if this helps — and feel free to sign up for the newsletter! (You can do so here.) I’m working on creating lots of goodies and freebies for subscribers, and being a member of the community gives us a direct line of communication together if you have additional questions :)

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