From Corporate to Freelance/Solopreneurship: A Survival Guide

Forget everything you know. Kinda.

Hello there. You are reading this because you have likely spent years, maybe decades, in Corporate America, and you are wondering if it’s time to leave.

You’ve had enough of politics, return-to-office policies, and working with people you have to pretend to like. You think it would be great to work from a venue of your choosing, with people you like, making as much money as you can.

In other words, you’ve heard the siren song of entrepreneurship, and you’re wondering if it’s time to jump ship.

What the sirens sing about is mostly true. There will be days you can work from wherever you want, with people you like, and you can make money.

However. While your years of expertise are valuable on the market, you’re entering an entirely different world, with different customs and expectations. Before you make the jump, it is important to familiarize yourself with this world.

This guide aims to make your first year easier.

It is not designed to help you avoid falling flat on your face, experiencing failure, or pure existential/psychological panic. You are nearly guaranteed to do all three before your journey is over - but all will make good fodder for trauma bonding, cocktail party stories, and/or Substack posts.

1. You are now in sales

You need clients, and you’re the (only) one for the job. This probably the single biggest barrier to entry for solopreneurship - people realize that they have to get out there and sell. They have to put themselves out there and talk about their business in-person and online. Terrifying.

But not for you. You can do this.

You will need to get extremely specific on your positioning and practice communicating it over and over, in as many different ways/formats/stories as possible. The more you practice, the better you get at it. The better you get at it, the easier it becomes to get clients.

Pick one platform where you think your clients are and be visible there 2-3X a week, start building an email list, and tell at least one person about your work a week.

Maybe you’ve already started with one high-paying client (maybe your old company!) and you don’t feel the need to go out there and sell. Do it anyway. Talking about your business in public gives you a visibility and an optionality you will appreciate: especially if your main client goes in another direction.

2. You are now in operations

You now need to figure out how to scope, write contracts, invoice, file taxes, and manage client work.

This is often the first function that people outsource, and with good reason. At the very least, make sure you have a separate business bank account. Get a bookkeeper (yes, you need one, no they aren’t the same as an accountant). Start here if you don’t know any - this is who I use.

3. Jargon does not help you anymore

When you were in Corporate America, you said things like:

“We unleash our capabilities while sitting at the intersection of culture, community, and authentic discourse.”

People nodded then, but no one knows WTF you are talking about besides that small group of people who speaks your language.

You’re going to be out in the world, pitching your business and your work to real people who are time-strapped and may not speak corporate jargon. Clarity is your friend. Make it obvious what it is you do, how you help, and what you want.

It matters more than anything that you are clear. Not that you sound smart.

4. You do not have enemies

If you’re a shit talker, cut it out now. If for no other reason than these people may have connections to future clients. (Also, it’s mean, but whatever.)

Be kind, be generous, and if someone pisses you off, tell your friends over drinks. Don’t talk about it publicly (unless you’re anonymizing facts heavily, and even then, be careful. I once did this and accidentally anonymized the facts to fit a DIFFERENT person, and I got in trouble.)

Assume everyone knows someone who might hire you. Don’t give them a reason to refer your work to a competitor.

And by the way, speaking of your competitors - they’re not your enemies either. Be friendly with them. They have similar challenges, may refer business to you when they have overflow, and may share resources and contacts with you. When I was a brand agency owner, I had other agency owner friends. We swapped tips on invoicing software, shared graphic design recs, and referred each other business.

5. No one cares

People do not care about your burgeoning business as much as you do.

This is a blessing because you should feel less burdened by self-consciousness when you are out there talking and posting about your business.

This is a curse because no one cares enough to help you get clients out in the wild - if they mention they’re looking for a new Botox lady, an accountant, or a life coach, they may or may not think to bring you up.

There are ways around the curse (referral programs, specificity in what you do), but in the meantime, take comfort in the fact that people aren’t thinking about you.

6. Get a buddy (or several)

This is a lonely, lonely road. Your friends who haven’t tried this before will support you, of course, but they don’t really know what it’s like.

Find groups - either in the world or virtually - that consist of entrepreneurs and solopreneurs.

THIS IS NOT LAME. Seasoned, accomplished entrepreneurs already do this. In fact, some PAY to be in certain groups that do this.

Also, the power of your network is a real thing. Help other people in your network, be generous, and let it support you, too.

7. Help first, pitch later

You will get absolutely nowhere if you are just going around talking about yourself.

Be helpful to other people. Support their content and their businesses. Don’t give away work for free, but give some advice for free.

Invest in real relationships and friendships. The chance to talk about your work and your business WILL happen. You don’t have to force it into every single conversation.

8. Not all selling looks like pitching

You might post about your work, what’s happening in your industry, comment on people’s posts with your own thoughts, or even like someone’s status update. All of this counts as soft-selling and putting yourself out there.

You don’t need to be talking about your business and your offer every damn second. Shoot for a percentage of your content (maybe 40%) that looks like this. The rest of it should feel “soft” and just keeping you top of mind.

9. You’re gonna make a mistake that costs you money. It’s OK.

It will likely have to do with undercharging for a service, poorly estimating your costs, or something tax related. The last one is inevitable (unless you are an accountant) because the tax system is not meant to be understood by anyone. Even the people within it.

These mistakes will cost you money, it will suck, but you need to just call this “entrepreneurial tuition.” Learn from it, and try not to do it again. Mistakes that cost money happen to literally every entrepreneur. You are not stupid, and it doesn’t mean you’re not cut out for this life. (This is also why you need #6. People will be like, “I’ve been there!” and help you through it)

10. Be a kind boss to yourself

Nobody’s gonna celebrate you but you. No one’s gonna give you a day off but you. Don’t just brush past your accomplishments without acknowledgement or work without breaks.

11. You got this. You also don’t got it.

Both can be true in a day, and this is normal.

Either way, go do it. There’s value in executing when you feel like “I got this! (confidence building) and there’s value in executing when you feel like “I don’t got this” (resilience building).

I think that’s enough for now :)

Business [Comma] Woman is for anyone who gets hives at the thought of marketing themselves or having to go get clients. If you’re building a business around your skills, don’t let the marketing part get in the way. Whatever you’re good at: accounting, tarot card reading, window washing, marketing, therapy -if it’s legal, I want you to make money at it. If this article was helpful, please share it!