Why you’re going to freelance sooner or later (and how to prepare)

Most of you reading this have a job. You have a steady paycheck and health benefits. Good for you. A job is great if you don’t want to think too hard about what you’re going to do every day — your bosses mostly figure that out for you.

But even if you have a job, you’re going to be a freelancer one of these days. Here’s how that might happen:

• You might get laid off, downsized, RIFfed, whatever they’re calling it. A million people have already been let go this year. And chances are, you won’t find a new job right away, and might need to do something else to have an income.
• You might get fired. It happens. Bosses and workers often don’t see eye to eye, and sometimes it’s just because a new person is in charge and wants to make room for their own people.
• You might become a prominent enough thought leader or speaker that you’d like to strike out on your own.
• You might take some time off because you’re burnt out, want to spend time with your family, are dealing with a health problem, or find yourself needing to take care of a loved one in need.
• It might be time to retire, but you’re not ready to completely retire yet.
• You might just make the leap to freelance because you’ve always wanted to, and have the financial resources to try it out for a while and see if it works.

Take some steps now to prepare

Whether it’s voluntary or involuntary, if you find yourself as a freelancer, you’ll be a lot happier if you prepared resources for just this moment.

Here’s a list of what you might think about doing.

• Register a domain based on your name (bernoff.com, jbernoff.com, joshbernoff.com, joshbernoffconsulting.com, something like that). Build a basic web site on it. You can make it better when you need to.
• Write and post. Blogs, substack, or LinkedIn are all possible places. Just post a few of your ideas with the thought that you’ll want to go back and add more when you need to.
• Polish up your LinkedIn profile. You should update that at least once a year.
• Put aside six months’ salary in the bank or liquid investments. Hard to do, I know. But if you need it, you’ll be glad you have it.
• Join a professional association. Go to a conference. Make friends and network.
• Fool around with AI tools like ChatGPT, Perplexity, Claude, or Gemini. The time to learn them is now, not later when you’re desperately in need.
• Make a list of key networking contacts from your career. Maintain it. (You can use LinkedIn for this if you want.) Reach out at least once a month to smart, connected people who you’re glad that you know.
• Buy your own computer. It doesn’t have to be the fastest or thinnest — it just has to work for you.
• Consider where in your home you can most easily work without being disturbed during the day.
• Ask yourself: What do I know how to do that people would pay for? Consider taking classes to boost that skill.

When you actually get started freelancing, you’ll need a bank account and a way to make yourself more visible online. But that will be a really busy time. That’s why it makes sense to do the rest of this stuff when you’re still working.

A lot of freelancers started by accident and now they love the freedom to work on what they want, when they want. I did that almost 11 years ago and never looked back.

But even if that isn’t you, you’ll be a lot happier if you prepare for the possibility now.