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How Are You Going To Protect Your Greatest Asset – Yourself?


My favorite talk from this year’s DYFConf North America wasn’t about some new, highly profitable marketing strategy or automation technique.

It was “a cautionary tale about the awesomeness of being a superhero.”

My friend, Dr. Sherry Walling, spoke about some of the risks that affect us as freelancers and independent business owners.

Anxiety. Isolation. Failure.

These affect us all — though some of us do a better job at hiding it than others.

After Sherry gave her presentation, I knew I needed to share her talk with the DYF community and the world at large once the video was ready.

Below are my notes, and above you’ll find the full, unedited video.

Please take 45 minutes out of your schedule to really focus and take in Sherry’s talk. Your life, your business, and the lives of the people you love and care about could depend on it.

The Freelancer’s Dilemma

It’s all about us. Our mood. Our ability to follow through. Our brain and intellect. How much your life is either working… or falling apart.

Our business is all about us.

Entrepreneurship comes with a price, and that’s freedom. It doesn’t matter if you have all the freedom in the world but become a jerk. “What does it matter if you gain the whole world, but lose your soul?”

There are real threats to us as solo business owners.

It’s critical to protect ourselves from these threats and neutralize them immediately.

1. Acknowledge the risks

These are things that make us vulnerable to physical, relationship, and mental health problems.

a. Anxiety

The burden of running a business can keep us up at night. There’s often a swirling storm of emotion and uncertainty trapped within us, despite outward appearances.

You can’t breathe because your head is constantly full of ideas, things you should be doing, anxiety.

“To be alive, on some level, is to be anxious.”

Our intensity fuels our work.

Studies show that activation and physiological arousal leads to performance gains. But when our anxiety peaks, performance begins to fall off the side of a cliff.

Anxiety is contagious. You can sense and feel someone else’s anxiety.

b. Isolation

Many of us work alone in a converted closet at the back of the house. Freelancing can be a lonely path.

Too much isolation can lead to loneliness.

“It’s OK to be a lone wolf, but it’s not OK to be isolated.”

c. Failure

We need to cope with the certainty of failure.

Your talk at a local meetup might not go well. Your client might not like you work. The product you’re working on might flop.

YOU WILL FAIL ON SOME LEVEL. That’s certain.

How you handle your failure is what matters.

Do you end up convincing yourself that you’re not capable? That you’re not meant to freelance? That you should go back to working for someone else?

Don’t be afraid of failure. Don’t run from it. Learn from your mistakes, and revise accordingly.

(Some people are so focused on success that they let everything and everyone go around them. Don’t be that person either. You don’t want to ignore your failures.)

We’re fallible people who can be broken, especially when we put ourselves fully into our work — work that doesn’t always love us back.

2. Get serious about self-mastery and self-care

a. Track personal metrics

  • Write down what the high point and low point of each week was.
  • Track your daily mood (there are apps for this.)
  • Track your daily energy levels. How are you feeling? What’s exciting you?
  • What are you grateful for? Record a gratitude journal.

The point of doing this isn’t to judge or even make sweeping changes.

It’s so you can learn how to observe your inner life. Just to notice and to then make slight adjustments accordingly.

b. Be a stress ninja

Notice when you’re stressed. Your body will tell you.

If for the last week you’ve been waking up in the middle of the night to think about your business you’re unwell. You’re not at ease.

Once you’ve realized that you’re stressed, figure out why.

External? Clients, an individual in your life. Internal? Maybe you’re thinking about something from the past, or maybe there’s a big disconnect in one of your relationships.

Make a list and write it all down.

Determine if there’s something you can do about any of the items.

If there is, take action.

“I’m exhausted” -> take this Friday off and go for a walk on the beach.

If there isn’t, develop a coping plan.

“Do I need to double-down on my gratitude journalling? Do I need to surround myself with more positive things?”

Use your stress to fuel motivation, but don’t let it crush you.

c. Shape-shifting

Don’t work from bed. It’s for sleep and sex.

Have some physical segmenting in your life. This is who I am in this place, this is who I am in that place.

(Brennan’s note: I refuse to do email from my home office. I walk to the coffee shop when it’s time to do any email. When starting a new creative project, I try to escape from anything that has distractions I can’t avoid — home, my city, etc. — and break ground in total silence.)

Don’t multi-task your family and friends.

(Another note of mine: Have you ever tried to participate on a Very Important conference call from the passenger seat while you and your family were heading to a theme park? Yeah, don’t do this. Don’t mix the two.)

d. Retreats

Not time out, but time in.

An exercise in capturing personal metrics — but on steroids.

Dedicated space. No outside interruptions. No other responsibilities but to consider:

  • “How am I doing?”
  • “What am I doing?”
  • “What do I want to be doing?”
  • “What do I need to get there?”

Do this a few times a year. Work intentionally on your business during this time, and let the world around you go.

(Brennan’s note: We’re doing our first open-to-all DYF retreat next month in Colorado and have 3 spots left. In February we’ll be doing another in Thailand and have 10 spots available. Contact us if you’re interested in either.)

It’s really important to set aside the demands of the day and FOCUS.

e. Invest in relationships

The most powerful predictor of how someone will do when their world falls apart is how connected they are.

Not about having 85,000 Twitter followers. It’s about the 5 people who will drop everything to help you.

As a freelancer, much of our work happens in our head.

It’s easy to delude ourselves into thinking that we’re “special snowflakes” and that no one understands us.

There’s absolutely NOTHING that you experience daily that can’t be discussed with someone like your mom. Don’t let your work become an excuse to detach yourself from the people around you.

(Brennan’s note: I struggle with this, especially since I live in an area of the world where telling people you “make a living on the Internet” raises plenty of suspicions.)

Invest in your family and (non-freelancer) friends.

But also invest in professional relationships. Go to conferences or local meetup groups.

f. Forgetting to care about other people

All of the success in the world doesn’t matter if there’s no one to share it with.

Learn how to be generous and kind. Use your power for good. Become a mentor and supporter for other people.

You’ve been invested in, so you should invest in others.

When is it time to get help?

  • When you notice really big changes in sleep, appetite, etc.
  • When you find yourself crossing the line (you know what that means for you.)
  • Doing things that aren’t you.
  • When you really can’t focus. Not just a few days, but weeks of low productivity.
  • When the voices that live inside you that talk about hurting you begin to talk with authority.

Anxiety is the secret killer of our generation.

Even if you’re not suicidal or have no thoughts of self-harm, don’t allow tiny snowballs to form.

If you’re anything like me, you have bravado. A “can do” attitude.

“The project must be done by this date, so I’ll do anything necessary to do it.”

“I want to say yes to every opportunity brought my way, because of Fear Of Missing Out and an infinite desire to grow my business.”

Confession time… I can’t fall asleep without the TV or some other thing I can think along with playing in the background.

When I don’t have something on to occupy my thoughts, my brain will fill the vacuum with other thoughts — and then I’ll inevitably end up falling asleep nervous or anxious about tomorrow and what it brings.

I also can’t get a massage or go on a walk without thinking obsessively about what I should be doing, or what I’ll be doing next. The phone in my pocket extends my work environment to wherever I go, so I’ll end up aimlessly walking around the neighborhood, face in phone, scrawling out what’s next when I’m back in front of my iMac.

These are problems.

And for too long, I rationalized them as being part and parcel of running a business.

Like Sherry said, this is the freelancer’s dilemma. And it’s up to us to do everything in our power to put an end to it — the things that matter most in the world depend on us doing that.

“Everything has been figured out except how to live.”  —Jean Paul Sarte

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