Working Alone

10 Lessons for Freelancers, Contractors, and Consultants

Jill Carlson
Jun 20, 2018 · 7 min read

Last summer, an opportunity for some contracted work came my way that I couldn’t turn down. I soon found myself working with a lawyer to set up an LLC, wading through paperwork and contract language, and figuring out how to buy healthcare.

Over the course of the following 9 months, I expanded what I was doing, taking on more projects. I have loved working for myself. Not enough people consider it an option. I would recommend it to anyone looking to learn more about their chosen industry, but more importantly learn about themselves and their work style.

I have learned a lot of lessons along the way. I share them here in hopes that others might consider freelancing or contracting as an option — and that, if they do, they can be prepared.

1. Get Organized

Get a lawyer. Take the time to explain your goals to her. Invest time and money alike in a good working relationship with your lawyer early. Send her every single contract before you sign it.

Think through your accounting. Come March, you are going to have a headache of taxes to file. Keep good records: have a file for invoices, a document for expenses, and a drawer for receipts.

Spend time optimizing your own workflows. Think about where you want to work, when you will schedule meetings, and where those meetings will take place. Give yourself structure and build a support system as early as possible.

2. Hustle Hard

Network. Start by trying to take every meeting that comes your way. As you become busier and find more direction, ruthlessly cut back on these — but in the early days, put yourself out there.

Come to those first meetings having researched the person or the company. Have concrete ideas and action items for how you can help. Share what you’ve been working on and thinking about.

3. Don’t Do Work For Free

Knowing when to draw the line between pursuing a project to work with and starting on a formal engagement can be tricky. You obviously will need to demonstrate your value before you can expect a prospective partner to pay you, but you also can’t get caught doing too much work for free.

If you find yourself doing work for free, check in and make sure lines of communication are open about expectations and timeline.

4. Take Care of Yourself

Suddenly it’s 1pm. Your energy is dipping and every problem is just a little bit more annoying than it should be. You realize you haven’t eaten anything yet today.

This used to happen to me a lot. You’ve got to take care of yourself. And it’s not just remembering to fuel up. It is also about sleep and exercise.

Carry snacks with you. Stop for lunch. Set a time every night when you stop doing work. Block off periods in your calendar for workouts or down time. Whatever it is, stay just as disciplined about your health and sanity as you are about your work.

5. Find Support

You don’t get any of that anymore.

This is why it’s so important to find support — both in and out of your industry.

I have been very lucky to have a network of a few close friends who work directly in my industry who have turned into my trusted confidants, my advisors, and my mentors. These people understand the field I work in. They know the players. They can make introductions and they can course correct me. They have been my biggest proponents and gentlest critics.

I have also had several incredible friends outside of my industry on speed-dial. For 9 months, they have put up with me pinging them urgent sanity-check questions or bouncing hair-brained ideas off of them. They have kept me balanced in more ways than they know.

6. Turn Off

It’s easy when you are working for yourself to be “on” 24/7. It doesn’t help when the people you are working with are founders and entrepreneurs who also don’t turn off.

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This is me refusing to turn off at 11pm on a Saturday. It was not cool.

But this can result in you zooming in, closer and closer to the frame — to the point where you lose perspective and your work suffers.

Force yourself to turn off. Have balance and hobbies. Do things that make you stop thinking about work altogether. This might be a sport or athletic activity. It might be spending time with family and friends who have no idea what you do. It might be as simple as listening to music. Whatever it is, find it and do it. Your work will be better as a result.

7. Have Direction

This is fine, but if you don’t have a narrow theme or focus you will find yourself context-switching constantly. There is a massive cognitive load that comes with context-switching. Don’t do this to yourself.

Pick a niche or a theme and become the go-to person for that one tiny thing. This will benefit your individual brand. It will enable you to feel like you have a consistent identity. Most of all, it will allow you to tap into the synergies between the various projects you are working on, rather than getting pulled in 5 different directions.

8. Say No

Say no to meetings.

Say no to that 11:30pm Skype call with the maybe-interesting project in Asia.

Say no to the 5:30am follow up phone call with the team in Europe.

Say no to people who want to pick your brain.

Definitely say no to conference invitations.

Say no to meetings with investors looking for dealflow.

Say no to the people trying to hire you.

Say no to projects you don’t immediately want to work with.

Contracting, even more than in other jobs, is the practice of transforming your time into money. In order to do this effectively, you have to say no a lot.

This is emotionally exhausting. You are constantly disappointing people. Be gentle with yourself.

9. Pay Tuition

Head hanging, he followed his manager into a glass office. He apologized and said he understood that he should probably pack up his things. His manager raised her eyebrows and replied, “What are you talking about? I just paid a million dollars of tuition on you. You’ve learned the lesson. You’re never going to make that mistake again.”

When you work for yourself, you are paying your own tuition. Accept early that you are going to pay it all the time. You’ll pay it by going to meetings that don’t lead you anywhere. You’ll pay it by doing work you never get compensated for. You’ll pay it by misunderstanding the terms of an agreement. You’ll pay it by not having researched a project well enough before signing on.

Make mistakes. Pay tuition. Understand that it’s part of the process.

10. Own It

Sometimes people are just genuinely curious. “But what does that mean? What do you actually do?” You will get this all the time.

Sometimes people have good intentions and are just trying to give you advice. “In order to grow your career, you should really be building something,” they will say. Or they might offer, “that’s not a good way to make money long term.” They’ll tell you that you should settle down and find full time work. Sometimes they are saying this because they are trying to hire you. Other times they are genuinely concerned. It doesn’t matter. It will send you into an existential spiral about what you are doing with your life.

It will become a voice inside your head that keeps you up at night. It might come from someone you really respected. It might come from people you used to work with. Their confusion, and your own self-doubt, will sting in a way you can’t prepare for.

You have to remember that you chose this path not because you didn’t have any options, but because you knew you could create even more options for yourself. You need to remember that the work you are doing is valuable and legitimate, even if many people don’t understand why you’ve chosen this path. You need to look back at who you were or what you were doing six months ago and remember how much you’ve shipped.

Own the fact that you work for yourself, that it’s not conventional, and that you are forging your own path. I can promise you one thing: you will learn a lot along the way.

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