How to Start Freelancing Without Having a Mental Breakdown

Systems, tools, lead generation, tactics and tips to keep from going insane as a freelancer. The 101 to your freelancing business.


Freelancers have a unique position, it’s just you.

You are the only one standing between a lean work environment and a convoluted mess.

Your focus should be on automation & efficient systems first and foremost to easily manage the monotony while you get to work for your clients.

So, from my experience I’ve put together sort of a 101 for new freelancers and experienced ones alike.

I’ll talk about:

  1. Tools & systems to use
  2. How to generate leads
  3. How to go about outsourcing projects
  4. Negotiating with clients
  5. Following through

So, first off here are some tools and systems you can put in place to tremendously help your freelance work glide along with ease.

Tools & Systems;

  1. Sales funnel & CRM — Stride is perfect for this. If you want a very simple dashboard and platform to work from, sign up for Stride and add your clients to their sales process. You can easily uptick who’s a prospect, who’s been pitched, who’s signing up, who’s signed up, who’s an active client. All from one easy dashboard. No need for a huge, elaborate CRM. Keep it simple.
  2. Proposal solutions — BidSketch is a very simple & effective proposal software solution. You can set up professional looking proposals in seconds, using templates designed with high-conversion rates in mind. This is probably one of the most annoying pain-points with pitching a new client. Ruben, the founder of BidSketch, worked at an agency that created one of the largest proposal programs in the world, constantly converting 7 and 8 figure deals. He knows how an effective proposal works, and these proposals work. That knowledge coupled with a very easy to use and affordable web-app is absolutely a no brainer.
  3. Accounting — Freshbooks, simple, easy reporting, invoicing, accounting, and tax filing. It’s just a very simple solution for Freelancers and small businesses alike. Best part, it’s free unless you elect to use one of the paid options.
  4. Invoices & Billing — Stripe + Freshbooks. This combination is a invoice + payment processing dream team. It saves tons of annoying hardship, instead of having to get clients to send you Paypal or some other form of payment, it’s just a very simple and professional system. Stripe is an exceptionally simple payment processor with backend analytics and invoice tracking, easily syncing into Freshbooks and tons of other web-apps.
  5. Banking — Simple is an easy solution to banking for the tech freelancer. It has all of the integration you want, easy setup, easy dashboard interface and flawless design interfaces. Obviously you can use whatever bank you want, this is just a very effective solution if you don’t have a business account already.
  6. Communication — Skype, a no-brainer but sometimes over-looked. Skype is an easy way to have face-to-face calls, screenshares and have easy interface with your clients without annoying phone-calls. Aka they’re phone calls that work. Another way to communicate in a synced up fashion is through Basecamp, but more on that in a second.
  7. Notes & Information Saving — Evernote & or Google Drive. Keeping Evernote synced is simple and easy, searching within Evernote is a dream, and it’s easy to create a journal for each client. Google Drive is also an easy way to share documents, spreadsheets and information and keep it synced across all of your devices. If all you’re looking for is a repository for your information though, Dropbox is a great alternative to Google Drive, more on that in a minute.
  8. Project Management — Basecamp is the epitome of the perfect project management system. It’s very cheap (only $20/m at the lowest) and extremely powerful. Sync all of your discussions, text documents, plug in your time tracking (more on that in a bit) and integrate Google Docs. To-do’s and everything else you could need to manage your project are simply achievable with Basecamp. Invite all of your clients and have a very nice, clean interface to work from. It’s always nice to have a “home” for your client or project, and this easily suits that need.
  9. Website & Hosting — Squarespace or Wordpress + GoDaddy. Buy a domain for your freelancing business and set up a quick website. This is a fundamental but absolutely essential. You want a page that shows what you’re all about, examples of your work or at least a home for your practice that referrers can point prospects to. If you have a blog, keep it all together. Squarespace is a simple way to quickly set up a minimalistic but beautifully designed site in minutes and integrate all of your social media, blogging and other accounts under one roof. Wordpress is a little bit more of an elaborate solution, but you can easily find affordable themes on Themeforest or Themezilla and get rocking in no time.
  10. Business Email & Document Storage — Google Apps + Google Drive or Dropbox. Google apps is a quick way to set up a business email. Meaning “yourname@yourbusinessdomain.com” instead of having a “bigdaddy69@gmail.com” type address to send clients to. That’s a big no-no, get a business email ASAP. You have to pay for it now with Google Apps, even though you used to not, but it’s still the best solution. You get a nice Drive storage and other benefits. If you need more document storage, Google Drive is an awesome solution, but so is Dropbox for file sharing and affordable cloud storage.
  11. Time tracking — Tickspot or Eon. Oh, time tracking. My absolute bane of existance. If you have a client who demands hour reporting, you will undoubtably need a good system for it. If you prefer to work off of an hourly rate and hourly model, this is actually the perfect system for you. Tickspot has direct integration with Basecamp so you can keep your time tracked for each project all in one location, but it also has it’s own dashboard if you would rather not use the integration. It’s very easy to set up and simple to use. It even has it’s own time-tracking widget and desktop app, so you can quickly track time and switch between projects. Otherwise you could use Eon to track hours and simply add them to tick or another system.

Systems, however important, mean nothing without clients. As with any freelancer, you will realize quickly that most of your clients come through referrals. Here’s a quick way to generate more leads through referrals.

Generating Leads;

  1. Referral lists;

There are plenty of sites out there for generating referrals, some are more to-the-point than others. Some sites like Credo are aimed directly at generating leads for freelance marketers. Others like Dribbble.com act more like a “social network” for designers, but drive a ton of referrals for designers who’s work stands out.

There are plenty of these in every industry. The other form that these referral lists can come in is through an “Experts directory” which essentially is set up to establish who can work on a certain framework effectively. Some CMS’s like Shopify do this, creating a “Marketers”, a “Designers”, a “Developers”, and a “Photographers” list. Being listed on some of these lists can seriously improve the amount and the quality of leads you get, as they are already prequalified, and already interested in a platform that you have experience in or enjoy developing for.

2. Blogging;

Industry blogging can be one of the fastest and most effective ways to establish new clientele. By targeting topics, painpoints and struggles, or by just showing your quality of work, case studies and research you can gain credibility and clients through putting your work out into the world. It’s like a press release but not as salesy, and actually helps the potential customer. This really ties back to SEO and the effectiveness of organic traffic. If you set up your blogging correctly, you can get a ton of leads without ever having to buy inclusion or go through the death-race of cold calling.

I personally can root almost all of my clientele back to blogging. Post on industry blogs to get your name out there, connect with other bloggers in the industry, create a group of bloggers and pass around critiques to get better acquainted. Just as an example, I am an SEO and internet marketing consultant, so I’ve guest-blogged on Moz, Credo and some other industry blogs, as well as have my own pretty well established blog.

Share information on social networks and provide genuine value to others in your industry. You will get leads from both ways — referrals from friends in the industry, and through actual leads reading your content.

3. Social Networking;

Create relationships with people in your industry. Better yet, create relationships with people who don’t do what you do but work on the same field. So if you’re a designer, create relationships with marketing agencies that might need design work, or their clients need design work. They will most likely ship those leads off to you if they trust you enough. If you’re a developer, get relationships with designers who might need developer work done.

I personally am an SEO consultant, and I established a network with these types of personas, as well as ones in my direct industry. I’ve had plenty of referrals pour through from this avenue. The real golden egg though has been creating relationship from within SaaS companies within my niche. They don’t do consulting themselves, they provide a product for consultants, but they get tons of leads for consulting just because people recognize them as the leaders in the industry. My best and favorite leads have come from here, all prequalified and all well known and well established — all converted into current awesome clients.

Be real, be valuable, be straight-forward, be grateful and reciprocate anything anyone gives you with your own referrals. Spread the wealth.

Outsourcing Projects;

The true test of how successful you will be as a freelancer is how well you can markup and how well you can outsource the parts that aren’t your strengths.

There are plenty of ways to outsource this stuff, the most notable being Odesk, but you can find outsourcing opportunities everywhere. Essentially outsourcing could tie into the relationship building you do within social media. Refer clients off to a designer or developer with a markup and you keep the dividend. It’s simple but effective.

Negotiating Clients;

The true secret to outsourcing is being comfortable negotiating clients and marking up costs. You have to work like you don’t “need” the money. If you can do this you can succeed at marking things up. It’s easier when you really don’t need the money, albeit, but you should still work from that frame of mind — even if you do.

This also comes back to knowing budgets upfront and being able to gauge your negotiation. If you know a client rakes in $30 million a year, don’t be afraid to charge an arm and a leg. It’s obvious they can pay it, and even though it may be a ton of money to you, it may be nothing to them for the value they are getting. Always negotiate off of value, not hours. If a client says, “Woah you charge $5,000 a month for SEO?!” keep even-keel and reply, “You have a $30 million/year business, I am confident that we can get at least a 20% increase in your organic revenue in the first 12 months. Do you think it is too much to charge $60,000 for that time period when you will have a $6,000,000 revenue up-swing? It’s your call.” This will usually leave them speechless and ready to sign up. (caveat: make sure you can deliver and I recommend not making guarantees, wording is very important in something like this, don’t over-promise — under-promise, and over-deliver.)

Following Through;

Here’s the fun part — the actual work.

Once all of these systems are in place you still have to actually do the work. Everyone works differently, everyone has different systems to deal with different situations and everyone has a different checklist they go through when dealing with site designs, optimization, social media management, ppc management or whatever it may be. The point is when you are following through with a client, analyze everything. Be very aware of what efforts you are putting in.

Ask these questions;

  • What’s taking 80% of your time and only yielding 20% of your results.
  • What more can you automate?
  • What more can you create systems for?
  • What is falling through the cracks?
  • What helps your clients the most?
  • What is your favorite part of the workflow?
  • What are your strengths and what are your weaknesses?

All of these questions are absolutely essential to how effective you will be as a freelance worker, how many more clients you will get, how happy you will be doing what you’re doing, and at the end of the day, how successful you will be.

The followthrough is where you see the lapses in your systems. This is where you can improve and refine your process. Always be creating new efficient systems, this will make your work scale. Always find solutions to outsourcing, to communicating and the like.

The follow-through, the actual work is the most important piece of all.

But not for the reason you might think. Yes, this is what you actually make your money off of, but it’s in finding your weaknesses and establishing new systems that makes this the most important part. It’s what will make or break you from being an effective freelancer and gaining more money, or having to unfortunately find a day-job.

The last portion (but not least) is the emphasis on your clients. With all of these systems in place, you need to focus on following through for your clients. Everything revolves around them. You don’t have the luxury as a freelancer to lose all of your clients, or to not give them the time they deserve. You have to follow-up, you have to give them a good experience, you have to constantly help them and build the trust that they want to have. This wraps back around to the initial phase of getting referrals. The best referrer is a pleased client, end of story. If you have someone to vouch for your work, that’s golden. That is why you need to put systems in place to handle the rest, because if you don’t have time for your clients, you won’t have time to succeed.

Be smart, create systems, follow-through, be connected and work well.


I’m a content marketer and SEO consultant, having worked with brands like Best Western, Holiday Inn, MFG, Bidsketch & Olo to boost revenue through clever content and organic search. I’m also a consultant for hire.