Things I learned the hard way.

Every friend group has a know-it-all friend. The one whose sentences always seem to start with “well actually…” 

I confess that, in many groups, I am that friend. My childhood memories are studded with recollections of my mom pleading with me to, for the love of everything, “stop correcting your brother.”

I know it’s annoying. I can feel it being annoying, even as the words march righteously out of my mouth. So I try to reign it in, I really do.

But when writing a blog post titled “5 Lessons I Learned…” doing whatever I did, not being the know-it-all friend becomes incredibly difficult. So at the risk of being the Monica Gellar of the group, I’m just gonna take the filter off and give you this disclaimer:

Take the advice that feels good to you and leave the rest.

(Though, to be fair, it’s less an advice column for an aspiring business owner than a “note to self” that ~me of the past~ will never have the pleasure of reading. She learned these lessons the hard way.)

1. Your low seasons won’t define the big picture unless you let them. 

If your personal definition of success doesn’t allow for ups and downs, you’ll never feel successful.

There’s something about being a business owner that makes you feel simultaneously invincible and utterly broken. Like maybe you’re an irrefutable genius, or maybe you should just phone it in and never get out of bed again because you have NO idea what you’re doing. 

Entrepreneurship is not a game. It requires a strange cocktail of grit and fluidity, and not everyone can hack it.

One day, you’re poppin’ out of bed like a Disney princess songstress that has birds help her get dressed in the morning. The next you’re burrowed under the covers hoping that if you don’t make sudden movements, no one will notice you’re not “showing up.” 

The emotional whiplash can take a toll. Especially in the beginning, before our experiences shape our priorities. So when sales are down and you’re burned out (like, really crispy), overwhelmed, or feeling utterly directionless, it’s easy to think you’re just not cut out for it.

But a low season won’t define the big picture unless you let it. 

The truth is, the hard things never stop being hard. But your capacity for hard things increases. And as it does, business stops feeling so much like coal-walking barefoot and blindfolded. 

2. If you have a bad feeling about a project, don’t take it. If you take it and regret it, learn from it.

Trust your gut. If something feels weird, figure out why. If it’s up for negotiation, have a conversation. If not, say “thank you, next.”  You don’t have to explain your “no.”

While it’s borderline unavoidable to (even accidentally) take on less-than-optimal projects during your first year of business, checking in with your intuition can save you from a world of hurt.

Try your best not to ignore red flags because you want the paycheck. (I want to acknowledge privilege here. It may not always be possible to reject a project and risk forfeiting income.) 

There’s a difference between a project that will stretch you and a project that’s a stretch. Between being nervous to take on a big client and being wary of the scope. Between a client who wants to know what they’re getting and a client who’ll nickel and dime you to death. 

I’ve never thought to myself, “man, I wish I’d taken that project that didn’t feel right to me.” I HAVE grumbled “I knew I shouldn’t have done this” to myself more than once when the latent concern reared its ugly head halfway through the project.

If you do end up in a situation that leaves you banging your head against your desk, wondering how everything hit the skids so fast, resist the urge to beat yourself up. 

Whether you get smacked with scope creep (been there), ignore a red flag because you need the money (done that), or get into some other sticky situation, know that the experience is valuable, and will sharpen your discernment when it comes to future projects.

Things happen. Sometimes they’re your fault, sometimes they’re not. There’s always something you can do better, even when things go well. Don’t waste time dwelling on the “should haves.” 

3: Invest in the essentials & DIY the rest.

Repeat after me: you don’t have to start the way you want to finish.

You don’t “scale” a business that’s in a foundational stage. Starting a business and growing a business are different. Both are valuable, and both take time. 

The business you start isn’t going to be the business you end up with. There’s infinite room for growth, polishing, and streamlining. (This is either inspiring or overwhelming. TBD.) 

Unless you’re coming in hot with significant funding, the first year involves a lot of DIY’ing, self-teaching, and trial and error implementation. And that’s a blessing. It refines you- forces you to face what you don’t know, learn by doing, and form relationships. 

So don’t get caught up in all the Insta-noise telling you what your income goals, work schedule, and outsourcing timetable should look like. (See also: vetting your online resources. Everybody’s an expert on Instagram.)

However, there are places where an early investment can prepare you and act as a catalyst for sustainable growth. I call these my “early essentials.” They’re major things that I couldn’t have grown my business without in year 1. They were, in ascending order of expense:

• Client Management Software
  • (I use Dubsado, sign up with my affiliate link to receive 20% off your first year’s subscription.)

• Monthly Bookkeeping

• Brand Design

Everyone’s early essentials look different, and the investment timeline/priority scale does too. These weren’t my only investments, but they’ve had the greatest ROI.

Lesson 4: Things will change. It’s for the best.

Discovering new information and acting accordingly doesn’t make what you were doing before “wrong.”

As an Enneagram 1, I’ve always been a black & white thinker. Things are good or bad. Right or wrong. Allowed or not allowed. Helpful or destructive. And once something is labeled, it’s hard for me to redefine it, even as I grow, change my mind, or broaden my perspective. 

But business is basically saying “lesson learned” over and over again until you either quit or die. You’re always facing challenges that force you to think quickly and critically. A rigid mindset will shatter under that kind of mental pressure. (Hi, personal experience speaking.)

A growth mindset grounded in foundational values (these rarely change), will keep your head screwed on tight if nothing else.

It adds another layer to the whole “you don’t have to start the way you want to finish” thing. It’s not just that you don’t have to. You can’t. You won’t. Things change, and that’s good. 

This goes for business (strategy, service offers, systems, etc.) and relationships.

As you grow and change, you’ll likely outgrow some relationships. Maybe even ones you swore would be ~biz besties~ forever. It hurts, but it doesn’t make you bad or flaky. Treat the person with respect & gratitude, but remember that business relationships ebb and flow.

Most of all, remember that your growing pains aren’t failure.

You’re allowed (and encouraged) to change your mind when you learn a better way, find out you’re going 100 miles per hour in the wrong direction, or outgrow something you once loved. 

5: Build a business that works with your brain.

Not liking something about your business is a valid reason to stop doing it. Pivots in your strategy are allowed to be personal. 

I spent the first 6 months building a business that didn’t work for my (neurodivergent) brain. Coincidentally, I wanted to rage-quit everything 6 months in.

Not in a “this is hard, maybe I’m not cut out for it” kinda way. But in an “I hate everything I’ve built” kinda way. 😬

I was working too much for too little and never saw my husband, my friends, the sun, or the insides of my eyelids for more than 5 hours at a time. I started to resent the business and the work I was doing as I churned through fierce cycles of burnout.

As I explored the root of my resentment, I discovered that the problem was actually very simple. It boiled down to two things. 

1. I don’t like long projects. (I work better in sprints.)

2. I prefer to work with one client at a time. 

I was operating within a system I’d built for myself based on what I saw as the industry standard. (In this case, taking on multiple clients at the same time for 4-6 week projects.) What I didn’t realize was that doing things the “right” way was killing me. And as I am my only employee, it was really bad for business. 

I still objectively loved being a copywriter and a business owner. But the way I offered services had to change, lest I rage-quit everything with a dramatic flourish or feel one fry short of a Happy Meal forever. 

Long, harrowing story short: I started offering exclusively VIP-style services, which provide the quick turnaround and high-touch experience my clients want and love while letting me work with my brain instead of against it. (Check them out here!)

Lo and behold: they’re my most booked, most lucrative, and most enjoyable offers ever. It’s opened doors to create other services that honor my brain and my energy cycles. And business is fun again. Love that journey for me.

It’s my party blog and I’ll cry write if I want to.

The initial idea for this post included 10 lessons. As you can see, I only talk about 5. That’s because when I sat down to write, I didn’t feel like fleshing out all 10. So I tabled the ones that weren’t coming naturally for another post. (#contentstrategy, yeah?) 🤷🏻‍♀️

In reality, it’s just me taking my own advice (see: lesson 5, sentence 1) because hypocrites are annoying, and I already met my annoying quota being the know-it-all friend.

So help us all out. Leave some of your first-year business lessons in the comments! (And cry if you want to.)