How to Prepare for the Emotional Side of Freelancing

My dad sat across the table from me, staring down at his coffee. Through the walls, I could feel the rest of the family, focusing on what was happening in the kitchen.

A little earlier, after Glen talked to my dad, we announced our engagement to the rest of the family. I knew my dad liked Glen, but he clearly had something he wanted say to me. Alone.

My dad grew up in Florence, Alabama and was two years old when the Depression hit.

“Everybody’s house was in foreclosure,” he said. “But there was nobody to buy the houses, so we all just kept living in them. Eventually, when the government offered a new mortgage program to buy your home back, your granddad was first in line. It was a very hard time for everybody.”

After flying F-80 bombers in Korea, my dad married my mom, then very carefully studied his career options (he didn’t want to fly planes and raise a family — too much time away).

He looked for the most reliable option with a bright future, and became one of the first IBM computer salesmen in the country.

Because of his past, financial security was very important to him. Which brings us back to the kitchen table, staring at our coffee.

I fidgeted with my spoon. Dad stared some more. Finally, he looked up and said, “You realize Glen’s a freelancer, don’t you?”

What a relief! Yes, I knew he was a freelancer. Since I was a freelancer too, Dad was just worried about two freelancers in the same family.

22 years later, we’re still freelancing and loving it. But my dad did have a good point. Freelancing isn’t for everyone, and if you’re thinking about leaving a corporate position to go it on your own, there are a few things to consider.

If you Google “freelancing pros and cons,” most “pro” lists include a flexible schedule, being your own boss, working from anywhere, making more money.

Most “con” lists include the feast-and-famine financial cycles, finding clients, being a jack-of-all-trades.

All important things to consider. But what’s not usually included are the emotional challenges of freelancing and how to prepare for them.

If you haven’t been your own boss, let’s talk about the emotional challenges you may face at some point, and how to prepare for them.

Do you know why you’re doing what you’re doing?

You’d be surprised how many people don’t. What’s motivating you to become a freelancer? What are your goals? Are they meaningful? Oodles of volumes have been written on goal making and finding your “why” — and for good reason!

It’s literally the one thing that fills the gap between success and failure, when things get tough. Every year, I’ve found it helpful to go through a goal setting and visioning process. Then each week, I read through it again. It keeps me in touch with why I’m doing what I’m doing, and it’s incredibly motivating.

Motivation beats back the feelings of discouragement that can creep in, so keep your goals and vision close at hand and refer to them often.

Are you comfortable with the risk factor?

When you’re getting ready to invest, your financial advisor will ask how much risk you’re comfortable taking. If the answer is zero, you might want to reconsider investing.

Working for yourself requires a bit of the same pioneer spirit as investing. Stepping out into the unknown, no matter how well planned, is a risk. If you cannot abide the unknown, do not become a freelancer.

If you’re used to a steady stream of income and a 401k, this will be new territory for you. You’ll need to create a good, honest plan for your financial future and be sure to include a buffer to weather the lean times.

Emotionally, the financial ups and downs can create stress. If you’re a prisoner of worry, you won’t be able to enjoy your new freelancing lifestyle.

Best defense against worry? Plan well, take heart, smile, and keep moving. (Tip: If you’re awakened at night by a worry-attack, writing or journaling for 15 minutes can help it to pass and get you back to sleeping peacefully.)

Getting comfortable with risk takes practice, but with time and action, it definitely becomes easier.

As the band Three Dog Night reminds us, “One is the loneliest number.”

Even the most introverted introverts sometimes like to hear another voice. Be sure to create a work environment that includes a handful of friends and colleagues you can talk to throughout your journey.

Joining a mastermind group, interacting with like-minded Facebook groups, and talking regularly with professional and personal friends can help you keep your emotional balance and make good decisions.

If you’re an extrovert, then you’ll need even more communication, so reach out and surround yourself with like-minded peers.

Rejection is a normal part of the day as a freelancer.

Marketing anything means finding the people who like what you have to sell and by definition, identifying those who don’t.

Some potential clients are going to say no. It’s going to happen if you’re doing your job, so embrace it!

You don’t need 200 clients. In most fields, as few as five (yes, only 5!) clients will keep you busy and your coffers filled. But on the way there, you have to learn to deal with rejection.

Remember “no’s” are not personal rejections. Any number of reasons could cause a potential client to say no, which have nothing to do with you.

To get over a “no,” I have a little routine. First, I grab the list of all my good qualities. (If you don’t have one, make one! Ask friends or family members what their favorite thing is about you, if you can’t think of any yourself.)

Then, I leave my desk, get outside for a few minutes, play some uplifting music, dance a little, read my list of good qualities, read my goals and vision, smile for at least 30 seconds (even when I don’t feel like it), and then — get back to work.

That’s what works for me, but experiment and see what works for you. One friend plays with his kids. Another walks her dog. Another goes crazy on her drum set. Whatever works, do it, shake it off, and get back to work.

Also, the more possible opportunities there are in your sales funnel, the less important each conversation and client is. I don’t mean each client isn’t important, but if you have lots of lines in the water, it’s less upsetting if one isn’t catching any fish.

You don’t have to know it all (thank goodness!).

You’re an expert in your field. It’s why people hire you. But you’re not a financial advisor-stock broker-graphic designer-editor-transcriber-marketing coach-chef-teacher-creative director. And who wants to be?

Most successful entrepreneurs have groups of people they rely on. As you build your business, you’ll need web designers, graphic artists, editors, transcribers … to name a few. If you don’t know any, reach out to the freelancing community for recommendations.

So, get a team together. It’s the ONLY way to win. I’m not kidding about that. DO NOT GO IT ALONE.

The world my dad grew up in is long gone, and the freelancing world is growing. So build your skill set, create your marketing funnel, get your website ready — and think through the subjects we’ve discussed here.

Then take the leap. Freelancing is a wondrous and fulfilling way to live. Stay connected — you’re in great company.

This article, How to Prepare for the Emotional Side of Freelancing, was originally published by B2B Writing Success.

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Published: April 30, 2015

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