Getting the ball rolling with freelance work

over 5 years ago from

How did you get the ball rolling as a Freelancer and what should somebody with limited examples of work do to start picking up jobs?

Background: I've been working full time for the past 4 years, mostly in-house, and I'm proud of most of what I've achieved so far.


  • Hayden MillsHayden Mills, over 5 years ago

    One thing that surprisingly worked for me was to ask people on Kickstarter if I could design and develop a website for their project.

    I would go to a Kickstarter category that interested me, narrow the results to only "successfully funded" projects, then email those projects creators and ask if they would like some help. Some I did for free and others they would pay me with the money they just made off the Kickstarter project. It was a great way for me to get some freelance work and start to build a portfolio for sure.

    Hope that helps!

    26 points
  • Jon MyersJon Myers, over 5 years ago

    Don't talk like a designer.

    I see this rookie mistake often.

    Make it your mission to understand people's complaints, competition and business challenges.

    Your network is everything. I would focus on building that first and foremost.

    Surround yourself with entrepreneurs, and other makers, and avoid the kind of deep geek talk that goes on in here

    Make it about them.

    Think and communicate strategically through the lens of design and specifically, process those conversations as a business analyst who happens to use design as his/ her weapon of choice.

    If I were going to try and get the freelance ball rolling at this moment in time, obviously, you need the basics covered, but here is what I would do:

    • Focus on a slice of industry - consumer, medical, finance, etc..

    • Focus on funded startups - you can find out who is getting funding on a daily basis by having a process for monitoring Crunchbase - http://crunchbase.com/ - and Angel.co - http://angel.co/

    • Create a cold email outreach process - tailor custom cold emails that are extremely brief, which focus on 1. establishing that they may have interest in what you are offering and getting a follow up. 2. The next email that goes out should be focused on getting them on the phone (Skype, Hangout, etc..) as quickly as possible.

    • Have a proposal, onboarding process - have your standard proposal, contract and PM software ready to go, as you wanna look pro.


    Hope that helps.

    21 points
    • Tyreil PTyreil P, over 5 years ago

      Can you elaborate further on your onboarding process?

      0 points
      • Jon MyersJon Myers, over 5 years ago (edited over 5 years ago )

        Hey Tyreil, sure.

        That would be:

        1. Proposal creation in Pages. I have a standard template. It starts like a brochure that captures the big vision, then...

        1.1. Try to get to the exact details of the deliverables (screens/ pages, functionality) as you can in the proposal. Itemize that list.

        1. Set up a Dropbox for the prospect. I have a generic Dropbox folder hierarchy I use for projects and just copy it, and relabel it for the prospect/ customer.

        2.1. Add the proposal to an “Administration > Proposal” folder in Dropbox.

        2.2. Set up a Slack Team and create a “Private Discussion” for the proposal. This way their team or your team isn’t privy to all the details.

        2.3. Send prospect an invite to Dropbox and Slack to view and discuss the proposal. I have a standard email template that goes out with instructions on what to do.


        At this point - the customer is already (bought in to some degree) and this way, they are already on with two key tools we use in the design process, Slack and Dropbox.

        1. Prospect decides to move forward - I use Docracy, have a standard contract template, and cut and paste the exact deliverables list into the contract.

        2. Invoice via RoninApp+Stripe - Customer can wire the money or pay me via credit card on a secure payment page. Sometimes companies as us to break up the invoices, so they can earn points with credit cards. I insist on half up front for projects 50K and under. For larger projects, 50 - 150K+ we negotiate those terms and develop payment schedules that are tied to pre-agreed upon milestones and deliverables. Once we hit a payment that is tied to a body of deliverables, they have 5 days to pay.


        Will skip over Discovery, Plan, and Exploration (Ex., brainstorming, sketches, wireframes, etc..) here, not to say that is not as important, but much of that happens in Dropbox, hard documents, on paper, over Hangouts, or in-person. Here is a snapshot of my high-level Dropbox structure:

        Image alt

        1. Onboard the Project - this means, to get the project set up in Trello and integrated with Slack. Based on the features and spec in the contract, I create Trello cards so all details are accounted for and then here is my Trello category structure:
        • To Do

        • In Progress

        • Pending Sign Off

        • Needs Revised

        • Signed Off

        • Future Features/ Design

        As we complete the screens/ cards (there would be a checklist of the features) we will move those cards into "Pending Sign Off" - the customer will then review and either move the card to "Signed Off" or "Needs Revised" with the description (on the card) of what needs revised.

        This is all linked to Slack.

        As the cards are moved that is updated in the Slack Design Channel.

        This ensures we hit every single thing noted in our contract, and the customer is literally signing off on everything as we go.

        1. Typecast, Sketch Setup - After we have gone through research, the plan (gathering user stories, etc..) and exploration (wireframing, flow analysis) - I like to begin designing with typography first if the customer has no existing identity.

        I usually design with type right inside Typecast. Love that tool. I get buy-in from the customer, and if they sign off on the type, we move to the next steps and finalize the visual identity.

        At this point, we would also proceed with other style(s) creation, and/ or - use a customer's existing identity specifications.

        In this case, we open up Sketch.

        We start with creating a custom styles, UI kit - on a page, with it's own set of artboards.

        We then, get all the type set on artboards and turn those into styles, all the colors are set, all the form fields are specd, buttons and other elements are specd - and then - - - we set up other pages, for the actual layouts, and begin the layout process.

        1. Invision App - Lately (don’t hate my LV guys, do love the product, I have been using Invision App on some projects. For one, we are working exclusively in Sketch these days, thus, I love that integration. But more so, what I like about Invision - is it keeps some stakeholders from mucking around in the guts of a project when they don’t need to be.

        For example, I’m currently working with a venture capital firm and helping them launch a full on Bank. We’re doing designing the online banking system, mobile applications and will have involvement with in-Branch interactives at some point.

        Invision is good for this scenario, because I have a lot of stakeholders (investors) whose eyes will be on our final product, we will need their feedback in order to move forward, and Invision allows us to present things in a way to get that feedback without too many people mucking up the process to get there.


        The bottom line though with all of this - is this - the more you systemize the boring stuff, the more you can focus on design. It doesn’t really matter what tools you use. Just have something.

        Simply, you have to visualize the path of prospect to customer - have a process to support that path and leverage all these tools we have at our disposal to run the processes.

        Finally, this helps you look pro, and it attracts and retains customers.

        Again, hope that was helpful.

        Take care everybody.

        14 points
        • Tyreil PTyreil P, over 5 years ago

          This was a fantastic write-up. Thanks for taking the time to respond, and for being thorough. I hadn't thought of using Trello with Slack, or even using Slack to communicate with clients. I'll definitely have to adopt a significant portion of your process when I start freelancing.

          2 points
        • iñi goiñi go, over 5 years ago

          Thank you for writing this up, very helpful.

          0 points
        • Andrei ScarlatescuAndrei Scarlatescu, over 5 years ago

          Thank you for sharing this, it's great to read about other people's process.

          0 points
    • C___ F_____, over 5 years ago

      Thanks for all of the detailed replies, would you be able to let us know what kind of tone you set in your cold emails? It'd be great to see a sample if you're willing.

      0 points
      • Jon MyersJon Myers, over 5 years ago

        Honestly, it has been about 6 or 7 years since I sent a cold email. :/

        If I were going to do it today, I would be very, very targeted, specific and brief in my outreach.

        0 points
  • Spencer HoltawaySpencer Holtaway, over 5 years ago

    Be really clear and focused about what your offering is the companies you talk to. Being proud of your work is good, but it's essential your offering matches with their needs.

    When I was freelancing I realized my best bet to do work I wanted to do (and get paid for it) was to find startups so early that they had an idea and maybe a really rough MVP. What I could do from there would be to take the idea and focus it to: 1. work better for business (i.e. help get investors) 2. work better for users (i.e. just work better!) 3. look like something someone actually designed (visual stuff).

    I had a lot of interest but then, boom, a full time opportunity came up that I didn't want to let pass by so I took it!

    2 points
    • C___ F_____C___ F_____, over 5 years ago

      Sounds interesting and similar to the kind of work that I want to do. Thanks for the help.

      0 points
    • Kai HuangKai Huang, over 5 years ago

      Most of these early stage startups are quite strapped for cash unless they're already funded, though. Did you do pro-bono work, get paid in equity, or how did you convince them to pay you in cash?

      0 points
      • Spencer HoltawaySpencer Holtaway, over 5 years ago (edited over 5 years ago )

        I ended up not actually working for any of them as the opportunity at Shuddle came in, and I was really excited about it. I was working with another client at the time so didn't have time to get anyone else on the books.

        I wouldn't work for anyone who couldn't pay me my rate above the table, and I talked to plenty of those companies. It's a shame because some had great ideas but didn't have the cash to support themselves.

        I would have considered equity as part-payment in the event the product/service was something I truly believed deserved to exist (and therefore "had legs", so to speak). However, cashflow is the most important thing in business (even if you, yourself, are the business) so I would never make a no-cash agreement.

        When I got hired full time I was talking to four or five who had the funds to pay me for a couple weeks of work, which would have been plenty to keep me paying bills for some time.

        I'm sure other people have opinions and ways they do things, but these are the boundaries I was willing to work in.

        0 points
        • C___ F_____C___ F_____, over 5 years ago (edited over 5 years ago )

          How about pointing some of those startups in my direction? Ha. Just kidding.

          It's cool to know how people operate as freelancers. How did you weed out timewasters?

          0 points
          • Brian PelayoBrian Pelayo, over 5 years ago

            I've worked specifically with tech startups for the last two years in New York. And I promise you, at least here in NYC, a majority of startups here have money—either from outside investors, or personal funding. I've met many founders who are ex-stock brokers, ex-lawyers, or ivy league MBA grads. You don't have to work for free.

            The key is to be very clear and confident in your skills and your worth. Startup founders will ask how you work and your costs—be upfront and don't charge too low. And don't get discouraged when you get turned down, or people don't respond. I've found out that out of every 10 people I talk to, only about 2-3 of those conversations convert to actual business.

            The hardest part about freelancing is starting. And the biggest hurdle to get over is others knowing your freelancing. Don't be afraid to just tweet, facebook post, email, or yell that you're now freelancing. Even if it doesn't bring you work right now everyone will keep you in mind when something does come up.

            1 point
            • Spencer HoltawaySpencer Holtaway, over 5 years ago

              "The key is to be very clear and confident in your skills and your worth."

              That's the biggest thing I learned. A big part of that is being very clear about what you won't do for them and framing it as to why it wouldn't be valuable to them, but backing that up with why what you're proposing would be valuable to them.

              It's always a partnership in freelance, the way I look at it. You have to be giving them something, but they have to be giving back in working the way you want to work (that's why you're a freelancer, right?). If they can't, no deal!

              0 points
  • Savelle McThiasSavelle McThias, over 5 years ago

    Tweet people from agencies in your area and ask them out to lunch. It's rare that you will get rejected. Ask to talk to them about what they do, their thoughts on the industry and ask for advice. They always ask to see your work lol. But, don't ask them for a job or for work. If you make them feel great, they'll remember you next time they need someone for a job.

    1 point
  • Guillermo MontGuillermo Mont, over 5 years ago

    The best advice I can give is to make sure what is it you specifically do, and if necessary partner up with someone (like a front end dev with a designer). I started off by having people come to me asking for a design or illustration. Something like dribbble is helpful for that, but I would actually encourage networking. Designers that are too busy will happily pass design work to another willing designer. The same goes for developers, they'll always need someone to crank out a design for them to implement.

    0 points
  • Nick LooijmansNick Looijmans, over 5 years ago

    Back when I was a freelancer, I remember that I got the ball running after participating in the 2010 Rails Rumble—which is a 48 hour programming competition. I was asked by some devs I'm friends with to join their team. They all worked for the same software development company and they knew that I was going freelance soon. After the Rails Rumble our project got quite some traction on social media and my friends' bosses were impressed. They invited me for a meeting and asked if I was interested to work for them on a freelance basis. That's how I signed my first client. Since they were a development studio taking on client project, they were able to give me a lot of work. Meanwhile other companies got the word that I was taking on freelance work (thank you Twitter) and after 6 months of freelancing I had to say "no" more than I could say yes. My schedule was full for 2-3 months in advance, which is a great situation to be in.

    0 points
  • Suleiman Leadbitter, over 5 years ago (edited over 5 years ago )

    To promote yourself you sometimes have to go for the long run. Pace yourself and stick to your goals. Most of the time it's about promotion and being the guy that did 'xyz'.

    Ages ago I did something where I had no work coming in so I designed just in Photoshop (didn't even code) a WordPress theme a day for just ten days. I kept it simple I only designed the front page. I managed to get half way through day four and calls were coming in. I never even finished the ten.

    Currently, I'm doing something similar for promotion, education and fun. Creating a icon each day for the whole of this year. This is quite a dedication and I would usually recommend doing something so long but it's also a personal goal.

    You can view how successful or a failure it all is here - 2015 Icons.

    0 points
  • Sarper Erel, over 5 years ago

    There'a book of interviews on this particular topic is coming out this month by a very close friend of mine. You can check the Kickstarter campaign here : )


    0 points
  • John HowardJohn Howard, over 5 years ago

    Shameless plug, but I created www.devboxdaily.com specifically for those in the design/development fields to obtain leads without the headache.

    Other than that, try and work with existing agencies. I have found that partnering with agencies (as a freelancer) allows you the freedom to work freelance and charge a higher rate, while they don't have to worry about the tax situations and managing an employee.

    Also, make sure you have your own website (not just a dribbble account) with work that you have done and an easy way to get in contact with you. Obviously elance and those sites compete on price so I wouldn't even mess with them.

    My first two months as a freelancer were tough but I just put my name out there to friends and family (as well as agencies that knew me) and I worked my tail off for little money. Once I had a few months under my belt and more example work (since my previous agency wouldn't let me show all the work I did for them due to NDA's), I was able to then promote myself based on legitimate work and charge what I wanted to. Hope this helps. If you have any other questions on the leap, feel free to hit me up on skype at 'blackairplanelabs' or twitter at 'freeosin'.

    Good luck!

    0 points
  • Adam ConradAdam Conrad, over 5 years ago

    I got started by checking the HN freelancer posts at the beginning of every month. I did it from time-to-time when I had spare cycles and extra free time.

    0 points