How to Start Freelancing Without Having a Mental Breakdown

Sean Smith writes:

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.

His list is good, go check it out. I would add a few things to it:

  • Bench — The online bookkeeping service that does your bookkeeping for you. I used to do my own books (ahem, I mean I used to plan to do my books… they only got done when tax time came around or I convinced my wife to do them). No longer. And it’s all online so I don’t have to visit an office anywhere or wait for an appointment.
  • CFO Andrew — An independent CFO/CPA for Freelancers & Solopreneurs. I used to research my own tax questions and prepare my own taxes. No longer, and I don’t even have to go see anyone or wait for an appointment— I just send off questions from my phone as needed. My understanding is Bench can prepare my taxes too, but I like using a CPA because I often have other questions that come up throughout the year that aren’t just return preparation related.
  • A small business credit card (I had a good experiencing getting a Capital One Spark Business Credit card when I had very little credit) — Put all business expenses on this card and set the balance to be paid in full each month if possible. Doing this builds credit for things you are going to be paying for each month anyhow and also buys you another ~21 days of cash flow (since the credit card balance will carry it at 0% interest until your next statement is due). I have mine set to automatically get paid each month in full, but from time to time I may override this and only pay the minimum (or some other less than full payment) for cash flow management purposes. This gives me additional flexibility in that way too.
  • Fundbox — a simple way to fix cash flow (on occasion) by getting advances on outstanding invoices (you get a loan against the invoice amount immediately after you issue an invoice to a client — it gets deposited in your checking account the next business day — regardless of when the client pays you). This is handy, albeit costly. Use it when cash is tight and clients are slow to pay, but come up with ways to solve your cash flow issues in other ways over the long run. Even so, cash flow is key when you’re a small business and having multiple tools available is handy when cash crunches crop up. Fundbox integrates directly with Freshbooks.

The Business of Freelance: Tales of a Full Service Freelancer (Video)

Freelancer Michael Jones (of Mograph Mentor) did a pretty bad ass presentation (video) for a user group on The Business of Freelance based on his personal experiences and a broad economic examination of working as a digital creative services freelancer. His video presentation is 19 minutes long and well worth it. The good stuff starts just under 2 minutes in, but the first part gives you some context on his professional experience.

Do Freelancers Need to Have an LLC/Corporate Entity?

Over on the Dr. Freelance Jake Poinier answers a reader’s question about LLC/corporate entities for freelancers.

My own view on this is that even if you don’t form an entity (initially or ever), at least acquire an EIN (also known as a Federal Tax ID Number) just for your business activities so you don’t end up giving out your Social Security Number (SSN) to clients…

Getting an EIN was one of the first things I did because there was no way I was going to be handing out my personal SSN to clients. And doubly so when I’m doing information security consulting for them. 🙂

It was a pretty simple online process a few years ago and I even got it instantly (which was good because I needed it for a new client request that day)! It looks to be the same straightforward online application process to get an EIN from the IRS these days. Anyhow, go see what else Jake has to say on the LLC/incorporating topic and decide what makes the most sense for you. (The specifics of this are US-centric, but the principles apply elsewhere I imagine.)

What are you afraid of?

Alan Weiss writes in the Million Dollar Consulting Mindset newsletter:

Too often our personal “driving force” isn’t composed of our strengths and passions but rather of our fears. We are afraid to confront an issue; to start a conversation; to pick up the phone; to try something new. We are “driven” in another direction entirely, to procrastinate, make excuses, abandon a plan, endure a poor relationship.

As the same poles in a magnet repel, we are “repelled” in a different direction, antipodal to our intended goals. “Fight (our fears) or flight” results in flight. This makes us not only unsuccessful, but also uninteresting.

As with any problem, to remove it we must find the cause. And in this case the cause is almost always an ego problem, poor self-esteem, “baggage” being borne for no rational reason at all. We fear rejection, we fear a “loss,” we fear ridicule, we fear “defeat,” we fear fear itself. Our fears are, of course, irrational, because they create a far worse future than any pain in confronting the obstacles would actually produce.

How one person provides high quality support to 4 million application users

Brian Cervino on how he supports Fog Creek Software’s four million strong user base for Trello:

As we pass four million Trello members I thought it would be a good time to share with other small software development teams the fact that providing high quality support doesn’t have to be expensive or impossible.  This includes a one business day initial response window for all newly created cases and making sure to follow through on all open cases until resolution.  With just a few tools and some dedicated time, it is possible for even just one person like myself to support our entire member base.

Pretty damn impressive.

Is “sales” a dirty word?

Justin Jackson writes:

“Making sales” feels kind of sleazy, doesn’t it?

For a lot of us, our feeling about sales stems from a bad experience with a salesperson.

The problem is, most salespeople are selling someone else’s product; they’re not directly invested in the product itself. A car salesman is a good example: he doesn’t design, build, or distribute the cars, he’s just responsible for moving them off the lot. This can lead to the kind of predatory behavior that we dislike about salespeople.

But you’re different.

You’re not selling someone else’s product.

Sales and marketing are very difficult topics for a lot of solo consultants and freelancers (and entrepreneurs generally). So much so that it often kills their business aspirations (or makes their lives far more painful than necessary during the first few years).

It’s important to unlearn the belief that marketing and sales are inherently bad. (They’re not.) Both are tools, necessary ones at that. How you choose to implement them in your own business is entirely up to you. You can create more cynics… or create more value in the marketplace.


Be authentic in your communication with said marketplace.

An advantage most solo entrepreneurs and small businesses have over corporate marketing: it’s easier to be “human” because there is less abstraction between the market and the creator. Take advantage of that strength.