J.D. Moyer

sci-fi writer, beat maker, self-experimenter

11 Ways to Succeed as a Freelancer


Lance at the ready!

I’ve worked as an independent contractor for about twenty years (with a few breaks to try out working full time, or not working at all). I always came back to “freelancing” (I love that word — it implies you’re in armor, on your trusty steed, ready to ride into battle in exchange for a full coin purse) because of the flexibility, high compensation, and variety.

Blog reader Marcin asked awhile back for insights on freelancing. I’ve done my best to compile a few insights below. Some of these came easy, others “the hard way.” My own field is database application development, but I think the ideas will carry over to most types of freelance work.

1. Go Where the Work Is

It doesn’t make sense to take on the uncertainty of working for yourself unless there is work to do. Generally it’s not a good idea to develop a specialized skill set and then spend time searching for a where to apply that skill (and try to get paid). Successful freelancers find the work first, then find a way to do it (learning new skills as needed).

I think many freelance careers get started with a regular job. If you and your current employer can come to an agreement — specific work for specific compensation — it may benefit both of you. You’ll gain more time, more freedom, and higher hourly compensation. Your employer stands to pay less tax, and less money overall to retain your specialized skills.

2. Your Client’s Success = Your Success

Help your clients succeed. Own their problems and provide solutions. If you adopt this attitude, your clients will come to trust you and depend on you.

3. Underpromise and Overdeliver

Build “buffer time” into your estimates and quotes, both in terms of billable hours (or days) and actual time. What initially sounds easy invariably isn’t — if the work were easy they wouldn’t be paying you good money to do it. Expect hidden complexity, additional requests not included in the original specification, and unanticipated problems, all as a matter of course.

Once you’ve underpromised, work hard to come in below budget and ahead of time. Once again this will build trust in the relationship and you will come to be seen as reliable and dependable.

4. You’re only as good as your last job.

If you blow it, don’t expect to be hired for the next project. As a freelancer, you’re free to say yes or no to both projects and clients, but so are your clients. Don’t expect loyalty.

So try not to blow it. Come through for your clients. Deliver results, not excuses!

That said, you might get fired, and then rehired, and never know it. If you mess up, salvage things as best you can and don’t burn any bridges. You might receive a call in a year or two, when your client realizes you didn’t do such a bad job after all (maybe they tried hiring someone else who did an even worse job).

5. Try to maintain at least five active (or semi-active) clients.

Usually one or two clients will take up the majority of your time. But invariably, even if you have been delivering quality work, things will slow down. Maybe your main contact at the organization will go on vacation, or get a new job. Maybe your client will switch technology platforms, or business focus, or even move operations to a different city. Expect change.

The only way to have a steady flow of work as a freelancer is to reach “critical mass” in terms of the number of clients you support. This will require you to be able to handle multiple simultaneous projects and “crunch times,” but it will provide security in terms of income flow.

6. Expect your clients to mirror your behavior.

Your clients will probably mirror whatever standards you set in terms of communication style and habits, so consciously set a standard you are comfortable with.

For example, if you don’t like working at night, don’t call or email your client (or respond to emails or calls) after 5pm. They’ll quickly get the message.

When I communicate with a tone that is friendly but semi-formal, my clients respond in the same way.  I prefer it when communications are concise, clear, and specific, so I apply those standards to my own communications and generally find them mirrored back.

7. Don’t tolerate abuse.

One of the joys of working for yourself is that you never have to tolerate tyrannical or even unreasonable behavior. This has almost NEVER been an issue — I really like the vast majority of my clients — so when recently someone associated with one my clients was unreasonable and rude during a phone conversation, I was genuinely surprised.

I resolved never to speak with that person on the phone again. I expressed this intention to my client and they were 100% supportive; it turned out there was no need for the two of us to directly communicate. Problem solved.

Very rarely you may find that you can’t tolerate the communication style or demands of a client. In those cases you can “fire” your clients, or explicitly state your communication requirements and allow your client to either conform or find someone else to do the work.

8. Understand and master your internal monologue.

It’s likely that as a freelancer there will be times when you feel confused, lost, and overwhelmed. This could be a result of taking on more work than you can handle, encountering difficult problems, asymmetrical expectations, or communication breakdowns.

At times like these, don’t talk yourself into a pit of despair. Problems feel unsolvable until you solve them (and then, with hindsight, you usually realize they weren’t that hard).

Use language to reduce the intensity of your emotions, when necessary. Why not consider an “impossible” problem to be “a tad challenging”?

Usually, when you feel overwhelmed, you need one of the following:

  • a break
  • a good night’s sleep
  • someone in your field to bounce the problem off of
  • more information from your client

Try to avoid words like “impossible” and “can’t”. Instead, look for ways to deliver value to your client. And remember most clients will be open to alternate solutions and unconventional approaches as long as they work.

9. Bill fairly (fair to both your client and yourself)

Your client should have the experience of getting good value for the money they pay you. That feeling is more important than the actual amount of money, so make sure they get it. Regardless of how many hours you put into the project, the client’s feelings about the end result will have more to do with:

  • Did the deliverable match or exceed their expectations?
  • Did the deliverable make them look good?
  • Did your work make their job easier?
  • Did they feel listened to and respected during the work process?
  • Did you respond to change requests and other service needs in a timely, helpful manner?

Your clients will feel much better paying $10,000 for a product and process that feels high quality than $5,000 for a difficult process and a shoddy deliverable. Fairness in your client’s mind corresponds to value received, not the actual amount of money.

The amount you bill should be fair to you as well. As a freelancer you will be paying for things that most regular employees have covered or subsidized (health insurance, self-employment tax, savings plan, and so on). Of course you need to consider what price the market will bear, but don’t charge too little for your services.

10. Don’t disregard “small” clients

Make sure you maintain your high standards for quality at all times, even for “small” clients. You never know when a “small” client might turn into a tsunami of work and money. The tiny project you’re working on might only be the tip of a gigantic iceberg.

11. Love What You Do

Even more important than “doing what you love” (though I’m not knocking it) is loving the work you do have.

But how?

For most people, helping people feels good. And getting paid well to do it doesn’t hurt. So that’s a good start. Deliver great value to your clients and feel good about it!

Often the “bad” parts of a job can be eliminated by simply choosing to do things a different way. I have a “don’t” list that I’m strict about. I just avoid the following, because I’ve learned over times these are the precise situations and circumstances that make me miserable (and life is too short to make yourself miserable on purpose).

  • working with a slow or unreliable internet connection
  • working nights or over the weekend
  • working when I’m tired or hungry (take a nap or eat instead)
  • working more than about twenty-five hours a week
  • working for organizations or companies who I don’t think are acting ethically or creating real value

These rules aren’t hard and fast — sometimes I’ll do some work in the evening for a client if it will really help them out. But there’s no reason to work under poor conditions when you have the choice not to.

So avoiding pain is half of the equation. The other half is actively enjoying the work. I find that I consistently enjoy my work more when I do the following:

  • when I’m friendly with clients and get to know them as people
  • when I strive for the highest possible quality
  • when I take the time to learn new techniques and methods
  • when I frame problems as puzzles or challenges
  • when I push myself to learn and use new tools and languages
  • when I take time time to optimize my working environment (light, sound, music, fresh air, ergonomics, etc.)

Remember that deferring happiness until you are successful is always the wrong strategy. When you succeed, your mind will simply pick a new success target, and you will be stuck deferring happiness forever!

Instead, find ways to be happy moment to moment, in the work. Feeling good will increase your effectiveness and chances at success.

Square One

If you are just starting to think about a freelance career, I would recommend this post from Ramit Sethi. Ramit makes the excellent point that everyone has marketable skills, and he provides some tools to help you think flexibly about your own skills (which you might take for granted … it’s easy assume that just because you know how to do something that everyone else does too).

I hope this list was helpful for you freelancers and aspiring freelancers. Please share your own insights below!


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  1. John C Moyer

    Since your mother is a Lancione (Lance person) this all makes sense!

    Sent from my iPhone


  2. Kuze

    Genius stuff as always, sir! Thanks for being a friend.

  3. grantsky1

    Awesome post. I too freelance and sometimes feel the highs and lows of working solo. That’s the point. In a regular employee workplace it felt monotone. Too level. Many of the points you mentioned are right on. I’ll use your post as important reminders. Thanks much.

  4. Marcin

    Thanks for the post, very useful stuff. Just one question, how do you get new clients? Is it all word of mouth or do you use some freelancer websites?

    • Yes, word of mouth. The rates tend to get driven down really low on freelancer sites I’ve seen, and I prefer to have longer-term relationships with my clients. In general the “piece work” that the internet encourages is bad for workers of all kinds … a real step backwards in terms of working conditions. Already as a freelancer you don’t have the protection and benefits a large organization or a union can provide (though there are unions for some kinds of freelance work).

      This is a personal bias and based on limited experience — if you’ve had good experiences with freelancer websites please let me know.

      If the work isn’t coming in, I’d recommend trying to get a job, or partnering with a reputable consulting business that hires freelancers (many of my own clients are via the latter … in those cases I’m the subcontractor).

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