There’s no denying that freelancing can require working long hours when racing against a deadline, especially in the early days. But you can – with some trial and error – keep healthy hours. Sooner or later, you’ll find your flow, learn how to automate your processes and discover what type of projects have the biggest impact on your personal goals.

Getting there, however, requires two big steps: 1) building healthy habits and effective routines, and 2) committing to trying new habit-building techniques.

Behavioral designer Nir Eyal says, “Habits are simply how the brain learns to do things without deliberation. These impulses can be put to good use, but only certain behaviors can become habits.” A routine, on the other hand, requires a bit more work. They are a series of behaviors regularly practiced, like writing daily. Eyal says, “Routines don’t care if you feel an urge or not, they just need to get done.” Building healthy habits is a great stepping stone for building routines. They get you on the right track to taking the actions that make you more productive without thinking about or dwelling on them. With that, here are five approaches to try when looking to build healthy habits as a freelancer.

1) Start small and build habits incrementally

We’ve all heard that the golden rule to building a new habit is to “start small.” Although starting small is an effective approach, it’s also overly simplified. After all, taking that first step is always the most difficult part of starting something new or changing a behavior.

To get used to building new habits, James Clear says to go super micro and start with an incredibly small habit. Make it so easy you can’t say no. James says, “Solve this problem by picking a new habit that is easy enough that you don’t need motivation to do it. Rather than starting with 50 pushups per day, start with five pushups per day.”

That “per day” part is important. To build a habit, you have to do that thing every single day – at the same time every day. That way, the action happens on autopilot without thinking about it. Like brushing your teeth, it will simply become engrained in your every day routine.

start-small build habits james clear

Now that you’ve established this small habit, the trick is to increase it in small ways. James added, “One percent improvements add up surprisingly fast. So do one percent declines. Rather than trying to do something amazing from the beginning, start small and gradually improve.” In order to make incremental changes, add one percent every day.

If that seems unmanageable and you find yourself wanting to give up, break your habit into chunks. Taking the pushup example, if you’re trying to reach 50 pushups a day, start by breaking them into five sets of 10 pushups each day. That will be much more manageable as you build up your strength.

The key to success when starting small is to be patient with yourself and celebrate the little wins. With each five pushups you add to your daily pushup routine, you’ll feel more motivated to keep going every day.

2) If-then planning for healthy habit building

Hundreds of studies have shown that deciding when and where you’ll take specific actions to reach your goal in advance can double or triple your chances for success. We already mentioned that a habit is an action spurred by a trigger. So, if you can plan what action will trigger your habit in advance and continue that “if x happens, I will do y” behavior, you will be more successful in building that habit.

Our brains are wired to understand if-then statements. It’s like programming your brain to make healthy, productive choices. Social psychologist Dr. Heidi Grant Halvorson says, “Since you’ve already decided exactly what you need to do, you can execute the plan without having to consciously think about it or waste time deliberating what you should do next.”

Examples of if-then habit planning include:

  • “If I finish lunch, I will spend 30 minutes answering emails”
  • “If it’s Tuesday or Thursday, I will hit the gym for an hour before work”
  • “If I spend one hour on a call, I will spend 45 minutes doing focused work”
  • “If it’s 6pm, I will do 50 squats”

Think about how streamlined your day would be if you strung a bunch of if-then statements together. Here’s an example: “If it’s Tuesday, I will wake up and go for a three-mile jog. If I jog, I will spend one hour writing. If I spend one hour writing, I will answer emails for 45 minutes. If I email for 45 minutes, I will spend 20 minutes meditating.” You get the point. If-then statements are simply a more habit-forming way to time-block your schedule.

3) The 3R method of building habits

Much like the if-then planning approach to building healthy habits, the 3R method is a framework built around triggers. The 3Rs to habit building are:

  1. Reminder: the trigger that initiates the behavior
  2. Routine: the behavior itself; the action you take
  3. Reward: the benefit you gain from doing the behavior

The 3R framework is also sometimes referred to as the “habit loop.” The concept is simple. If a reward is positive for an action taken, then you’ll want to repeat that action to receive that positive reward. Typically, a reminder (also known as a trigger or cue) takes place that sparks that action and reminds you of the reward given when completed.


For the 3R approach to work, your reminder needs to be something you’ll do without fail every day. Examples include brushing your teeth, drinking coffee, getting a text message or turning on your computer.

After choosing your reminder, pick a habit that’s very easy to start. Examples include walking around the block, doing one pushup, writing two sentences about your day, thinking of one thing that makes you grateful, meditating for three minutes, etc.

The final step is to choose your reward. It’s important that your reward doesn’t counterbalance the positive change you make. You probably shouldn’t down a cheeseburger every time you walk around the block. Your reward can be something as simple as congratulating yourself by saying “nice work.” Or better yet, find an accountability partner to congratulate you each time you complete your positive routine and do the same for them.

Stick with it and be patient. You may have to test different reminders but stay with it till you find the one that sticks.

4) Jerry Seinfeld’s “Don’t Break the Chain” approach

Jerry Seinfeld is one of the most successful people in the entertainment industry. Sure, it helps that he’s inherently hilarious, but his success also took a lot of hard work and habit building.

His secret? He spends some amount of time doing a desired activity every day and when he does, he crosses off that day on a calendar. This creates a chain of Xs showing your progress. If you don’t do your specified task on one day, you don’t get an X and that chain is broken. This is known as the “Don’t Break the Chain” approach to building habits and increasing productivity.


Because this approach doesn’t work when you account for sick days or vacation, it’s best suited for smaller goals like the ones mentioned above or for short-term goals. One Lifehacker writer tried this approach for writing, one exercise and keeping a clean house. His results after one week were 30 pages written, 700 push ups and 980 sit ups done, several miles jogged, and his apartment was as “clean as a catalog photo.” Here’s how he made the approach work for him:

  • Identify your goals (no more than three)
  • Set daily minimums to consider a goal accomplished
  • Set boundaries and rules (consider your chain like a mini job, it’s ok to get sick or take a vacation – just know what they are up front)
  • Print out a calendar and label it with a goal
  • Buy a fat red marker and start crossing those days off

5) The 30-day challenge approach

There’s a lot of speculation around how long it takes to make or break a new habit. Some say 21 days (which has been proven unlikely). Others say 66 days. Some studies say it depends on the person and the habits they’re trying to build.

Think of a 30-day challenge as a stepping stone to building awesome habits. Even if you’re not going to write a book after 30 days of writing, or run a marathon after 30 days of training, you will be writing a few pages a day or running a few miles a day. Doing something for 30 days gives you the opportunity to build a new habit.

30-day challenges are great because they force you to focus on one thing at a time. They also trigger our desire for reward, whether it’s a free month at a gym, congratulatory praise from classmates or to simply feel better about your health.

To successfully complete your first challenge, pick one small thing about your lifestyle you want to change. It could be cutting out alcohol, going vegitarian, running a mile a day, writing 1,000 words a day, etc. Before day one, create a check off sheet (or a calendar like Jerry Seinfeld’s) so you can mark off every time you complete your daily activity. Make it as easy as possible to complete your challenge activity. If you’re running every day, set out your exercise clothes before going to bed. If you’re writing every day, set up an enjoyable writing station for you to work from with your morning coffee.

Need motivation to build your healthy habits?

You may need to try a few of these approaches before finding which works best for you. There’s no shame in that. Just picking one and giving it a shot is a victory worth being proud of.

If you’re finding it difficult to get started, there are few things more motivating than having a support community behind you. Our community of Peeps chat with each other every day in the Facebook Group, providing advice, tips, resources and of course, motivation. If you need a new 30-day challenge buddy or want to learn about other people who’ve successfully built new habits – join the community. We’d love to have you!