I don’t know what’s in the air right now but between some of the more recent rounds of layoffs and usual B2B weirdness, I’ve been having more conversations with Creatives about going out on their own.

I don’t consider myself to be an expert in this. Sure, I’ve launched two businesses with The Creative Brand and OhSnap! but it’s not like I’m sitting here Scrooge McDuck-ing it—there’s still so much to learn. In any case, I wanted to share the big things I’ve had to learn the hard way as I’ve been building these businesses out. If you’re thinking about starting a side hustle or going out on your own full-time, there’s probably one or two things that you’re not thinking about… yet.

These are the lessons I learned the hard way

Starting a business

The first assumption I made was that I’d decide to go into business and clients would just line up with cash in hand. Turns out it doesn’t work that way. Before you start taking on clients you have some other work to do.

Looking back, these are the things I wish I did before ever getting started because without them I had to play catch up (and in some cases I still am). Think of this section as going from 0 to 1.

Start posting on social/ building your personal brand before you need it

I've been on Linkedin since April 2008, I didn't start posting consistently until December 2023. That's 15 years I could've been sharing and building my personal brand. There are missed DMs that could’ve paid off. Relationships that could’ve turned into jobs or other opportunities. Tons of value that just disappeared because I didn’t take action. When you’re ready to share news or make announcements, you want to be able to leverage a warm network and social is great for that. The only way to build a warm network is by being active.

Get your plumbing together

Start your LLC, buy a domain, publish a website, create a business page on LI (if applicable), lock down your social accounts, get a bank account, sign up for a credit card. All the annoying stuff, just do it. If you don't need it it’s no big deal, but you don't want to be stuck without these things down the road especially if someone cuts you a check and you don’t know where to put it.

You need to think about the money

Speaking of which, don’t get ahead of yourself but the goal here is likely to make a few bucks. Start thinking about pricing, how you want to get paid, tracking your expenses, potential marketing expenses, and don’t forget about taxes. Money is a funny thing in that if you don’t take care of it, it disappears quickly.

Figure out what you want to do

Not in an existential way but when I first started, I'd generally do anything for a check. It was a great way to experiment and figure out what type of work I actually enjoyed doing and wanted to do going forward. It was also a great way to learn what work I absolutely despised. If you’re working for yourself you have that choice. You can't be everything to everyone, so figure out what your thing is and lean in to see if there’s a business there.

Be ready to pivot

Since starting The Creative brand I've launched this newsletter and a podcast and a new company. I've narrowed my scope (Creative Ops) and then opened it back up again (Brand Systems which require Creative Ops). It's not indecision, it's seeing what's happening around you and adapting to it. In this world you need to be adapatable.

It's all about relationships at the start

At some point you'll probably want to make a big marketing splash but start by hitting up your network—the people that know your work and trust you. Let them know you're thinking about this path and offer to help them out. You'll make a few bucks and hopefully get a shiny new logo or two for your website. This is how you start building a client base and case studies.

Ease into it all if possible

Back when I was consulting as a side gig, getting 5 or so hours a week of work was easy enough. When I moved into entrepreneurship full-time I quickly realized that bumping up from 5 to 40 was pretty hard so if possible don't just dive into the deep end. Put together a plan to go from 5 to 10 to 20 hours a week and if you can sustain it, then maybe it’s time to jump in with both feet.

Get out of your comfort zone

This job has me posting, networking, appearing on podcasts, doing public speaking, shaking hands, and kissing babies. I'm a former engineer who just wants to sit in the dark with his headphones on. You need to be ready and willing to do what it takes to build your vision. A lot of this stuff isn’t as scary as it seems but it still took a giant leap at the start.

Understand that it's harder than you think

I've seen plenty of people go into this life only to realize it's not for them. That's ok! Building a business is hard. You're gonna win and you're gonna lose. You need to be able to deal with the lows otherwise you'll never see the highs. This is the quintessential short-term vs long-term dilemma because you’ll never get there if you don’t think about the short-term but if you’re not proactive then you’ll always be reacting.

Doing the work

Once you’ve decided that you’er going to get started and you’re in it, you should be cruising because the work is likely what you know best. That said, if you come from a large team or you were once the client or primary decision maker, things are gonna look a little different now (read: a lot different now).

It’s lonely AF

Not enough people talk about how isolating it can be to start a business. It’s just you sitting at your desk doing your work. No one to compare notes with, share wins or losses with, or just chop it up with. It’s one of the reasons I was so excited to start OhSnap! with Jenn—we're in it together now. In the past few years, new communities and networks have developed for entrepreneurs so find your people, but when it’s time to do the actual work prepare to be on your own.

You need to work on the business

It’s really easy to go heads down and focus 100% on client work but if you don’t create time to focus on the business (building your brand, updating your website, reflecting on how things are going, etc) it’ll stagnate. You’re your own greatest case study so take care of yourself and when it comes time, flex that self-care.

Build your processes

Obviously the What’s Your Process? guy is gonna tell you to build your processes but they’re how you scale. It might be too soon to worry about scale but it’s never too early to worry about lost time, redoing work, and speeding up the things you know how to do in your sleep. Use software. Use AI. Use automation. Use Excel formulas if you need to. Just don’t wait too long to do this otherwise you’re going to get in your own way of being productive.

Promotion is part of the work

I said it earlier and I’ll say it again, you gotta get in front of your audience. As more people share “thought leadership” there’s no greater proof of your ability than showcasing the work. You need to get it out there, you need to take credit for it, and you need it to hook your next client. A lot of the Creatives I’ve worked with over time have hated the spotlight but then would get upset about not getting the credit for the work. This is your time to take the credit.

Scope creep is real

You’re gonna want to help people (and make money) so you’re gonna say yes to lots of things. A few questions or a meeting here and there isn’t the end of the world but if you don’t stand up for yourself you’re gonna start losing money so put together an MSA, get a signed scope of work, and protect your time. If something is that important you can always write a new SOW.

It’s easy to be shady

You ever get tricked into buying new brake pads by a shady mechanic because you don’t know about cars? You can be that shady person too... but you shouldn't. You may get an upsell or two but it’ll get out that you're taking advantage of people and that always comes back to bite you. Help people with their problems and offer recommendations that they may not have considered but don't apply pressure and don’t sneak things in without approval. The way to grow long-term in this business is to build trust, so avoid that short-term decision as painful as it might be.

Everyone is gonna know better than you

Every relative, friend, colleague, and internet rando you talk to will somehow know how to run your business better than you. Not only that, apparently they're also experts in your niche—this will include the people who are paying you to help them. Feedback is a gift but only take what you need. The reality is if these people understood this life, they’d be quiet because what gets shared on Linkedin is only a part of the story.

You’re not your client’s priority... until you are

When you're only one person, bandwidth is tight. That's a YOU problem. Clients are going to do things when it's convenient for THEM. You may not hear from them for weeks at a time then all of a sudden you've got an urgent request you need to solve for. That's showbiz, baby! This is another reason why you need to have your paperwork together because your MSA should have language about feedback, expectations, and what happens if those aren’t met.

It’s not a collaboration

There's a lot you need from your clients or contractors but at the end of the day you're getting paid to own the work and you need to be comfortable making calls. Yes, you’ll ask questions. Yes, you’ll need their help on certain elements. But it’s on you to figure things out that’s why you were hired in the first place.

It’s not about you

You’re owning the work but the work isn't for you—it's for the client. They want a W and it’s your job to get it for them. You might be their hero when they get a promotion or raise but you're not the hero of the story, they are. Make sure you do whatever it takes to make them look good. If you do, there’s a pretty good chance you’ll get to do more work for them.

Sometimes you need to break up

This is a tricky one, especially early on. Sometimes it just doesn't work though. Maybe the working relationship isn't a fit. Maybe you're not getting paid on time. Maybe they don't like your work. There's a million potential reasons for this but sometimes it's better to just say goodbye and move on. It's hard but you'll feel so much better on the other side of it. When will you know if it’s time? You just will.

And you still have to do the work

With all of these considerations about doing the work, you still have to actually do the work. The paperwork could be tight, the relationships strong, and the money green, but if you don’t deliver then you’ve got a problem. I really hate to admit it but this is something I struggled a lot with at the start because my old fancy job didn’t require me to do work, it required me to sit in meetings (I realize that now). Getting your hands dirty again is a lot of fun but super hard!

“You’re not fired yet!” That was a joke a client made earlier this week. It still has me laughing. How do I know they were kidding? They told us that the meeting we just had—our first big one together—was fantastic and reassured them that they made the right choice in hiring us.

We’re helping them, a public B2B SaaS company, get their branded house in order after a series of acquisitions. It’s a huge project and a great opportunity to showcase the power of brand systems. That said, you don’t need 6 brands to work with us, 1 is just fine and I can promise that you’ll feel reassured in hiring us too.