I’ve been working for myself for the last decade and I’ve learned some lessons along the way, some of which I’ve had to learn more than once. While I’m a B2B (business to business) consultant, most of these lessons could be applied to any type of business.
In no particular order:
Desperation stinks and your potential clients can smell it
Any time I’ve felt anxious about income in my company and lowered my prices, given a potential client a deal, or offered additional work just to secure business, it’s totally backfired. I’ve either ended up with zero work OR with a terrible client.
As Beka Hicks commented on one of my more recent Notes, “This past year my most difficult clients were the ones that I had temporarily lowered my prices for when I felt scarcity mindset. So true every time!”
Before you give somebody a sweetheart deal just because you’re concerned about cash flow, pause, breathe, and reconsider. Are you going to regret this later?
Hire slowly, fire quickly (yes, this includes contractors)
When I was finally at a point in my business where I could hire someone, I opted to hire a friend of mine. She immediately proved to be a terrible hire (and we are no longer friends) but I continued to give her chances. She was consistently late with her work, full of excuses, and half-assed any work she did turn in. What did I do? I kept her on the books way past when my gut told me to cut her loose.
I repeated the same mistake with a couple more team members including an awful payroll company. I second-guessed my gut instinct thinking, “But what if they’re doing everything correctly and it’s just me?” Lesson: trust your gut.
Low prices = difficult clients
I used to think that lower prices = more clients.
It took me years to realize that lower prices = difficult clients.
When I raised my prices, my client workload decreased…but my time freedom AND my income grew.
Jennifer Stanley HR & Coaching wrote, “Thank you for sharing that valuable insight! It reminds me of some advice I recently received from a seasoned entrepreneur who’s grown and scaled his business internationally over a decade. He advised me to never discount my rates. Aligning with my own values, he said I should continue to do pro bono work for not-for-profits which fill my cup, but to never discount for my target client. I am still thinking about this guidance to this day!”
Take payment before you deliver the service
To make a long story really short, I met a guy at a networking event who invited me to consult for his company. He quoted my own rate to me on the phone and told me he would pay me when I arrived at his building. Although my policy was to always accept payment upfront, I gave this guy a pass because he was only 20 minutes away and I’d already met him in person—plus, he’d quoted my own rate to me!
Instead of trusting my gut (again), I showed up at the building and pulled out my credit card reader. The guy played dumb and tried to get me to provide my consulting services. I’m proud to say I got up and walked out, but I was furious with myself for ignoring my gut and my own business rules.
Not everybody is going to “get it”
I used to feel really lonely in my business.
I remember sitting around the table talking with friends who had “normal jobs.”
Bad boss? I was the boss.
Funny story? No one to laugh with.
Water cooler drama? My cats were my coworkers.
It wasn’t until I connected with fellow entrepreneurs online that I finally felt like somebody got it. Not everyone is going to “get” what you’re doing or understand what you’re working towards, but that doesn’t mean it’s a bad idea.
Working for “exposure” or “referrals” are the surest ways to ensure you never get paid
There’s no pitch that annoys me more than, “We’d love to have you speak at our event but we can’t pay our speakers. But you’d get great exposure!”
Unfortunately, I can’t pay my bills with exposure.
Anytime I’ve worked for free or for promised business, the money never arrived. People don’t value stuff they get for free, so your work is inherently devalued.
Clients who don’t pay on time are more effort than they’re worth
I had a client in recent memory who was consistently late to pay. When I say “consistently late to pay” I mean they were always months behind, every month. To make matters worse, they were paying via multiple channels and had multiple payers, all of whom we had to follow up with, track down, and generally bother in order to get paid. It was awful.
I was worried that if I dropped them, I’d miss that $5k monthly payment. As my accountant joked, though, “Rachael, they’re barely ever making that $5k payment as it is. I’d say you’d miss the money, but you’re not really getting that money in the first place.”
I was surprised at how relieved I felt when we finally dropped them.
If you stay in your PJs, you’re going to sleep on the job
I discovered something pre-2020 that most of my friends stumbled upon when their jobs went remote. Working from home isn’t easy, but if you stay in your PJs, it’s going to be even tougher. There were plenty of days at the beginning of my entrepreneurial journey where I’d hop out of bed and go right to my desk—big mistake.
Suddenly, it would be 1 PM and I’d be hungry, cranky, stiff and tired. I realized that if I was able to wake up, get dressed (even in athleisurewear), stretch (or work out!) eat and sit down, my day went a lot better.
Passive income is far from passive
If you’ve been online for more than five seconds, you’ve heard something about “passive income” and “how easy it is” to make. This is massive lie.
You have to protect your intellectual property—even though it’s going to piss people off
I have a number of trademarks and copyrights filed with the USPTO. The challenge with having IP, though, is that you have to continuously protect that IP.
Many people believe that once you have your official trademark letter, you’re safe, and nobody can use your trademark. Unfortunately, that’s just not the case.
We have an IP attorney and pay good money to have her track down infringers and reach out to them. It’s great when that takedown process is smooth and conflict-free, but ofttimes people get rude, aggressive and downright mean when they’re asked to stop infringing on your IP. (I even had a woman name me on LinkedIn in a long-winded post about how my attorney asked her to stop using our trademarked phrase!)
Block out lunch (and maybe Fridays)
2025 became the year I started (finally) protecting my time on my call scheduler. We use Calendly —you can use any product you want for people to book calls—but certainly use a product instead of emailing back and forth.
On Calendly, I started blocking out my lunchtimes every day so that nobody could schedule with me all the way through my lunch hour. I found that if I didn’t block out my lunch, I’d just skip it—and then be hungry and cranky.
Halfway through the year, I also realized that we could easily switch to four-day workweeks and not see any interruption in our work. I blocked out Fridays and haven’t looked back.
