10 Things I wish I knew before leaving my 9-5 & becoming an entrepreneur
I’m one of those people that likes to plan everything out. I take into account all the “what ifs” and make a Plan A, B, C, D, and E. You know, just in case.
So to say my transition from teacher to freelance copywriter to entrepreneur was a wild ride? It’s an understatement.
The world of entrepreneurship is one of those things where it doesn’t matter how much you read, study, learn, prepare…
You don’t truly understand those intimate details of everything until you’re in the weeds, going through the motions, and perhaps, struggling a bit 😅
When I left my cushy salaried 9-5 position and health benefits, I did so knowing the next step would be a challenge. I think we all know that when we desire to be our own boss. I was so focused on all the logistics of making this happen that I didn’t really focus on some of the lesser talked about details of what I’d be up against in this journey.
But with copywriting training and experience under my belt, and a desire to help others grow their biz through story, I decided the risk was worth it and I’d figure it out.
You better believe that I quickly realized there were MANY things I wished I had known beforehand (not that it would have stopped me but, you know, it’s nice to know)...
And while I definitely came across more than 10, these are some that really stood out to me.
One. Everything is sales
This one became obvious to me pretty quickly, and probably because I’m also wearing my copywriter hat. Because as a copywriter, I’m selling for others. But as an entrepreneur, I’m selling myself.
I think we need to reimagine the negative association we all seem to have with “sales.”
It doesn’t have to be the grimy, cringy tactics and bro-marketing strategies we’re used to seeing… and are so very sick of. Selling can be ethical.
Selling is nothing more than connecting people with a service that will help them solve a problem.
As long as you’re talking to your target audience, you’re truthful in what you’re saying, and you have a deep desire to really help them, there’s nothing gross about it! You’re in a position where you need to show others what you can do for them and what sets you apart from the competition.
And when you truly believe in what you’re writing about in your emails, social media posts, website, etc., selling really isn’t so bad. After you see the difference you make in people’s lives firsthand, it actually becomes kind of addicting 🤩
Two. Multitasking is BS
In my days of teaching, multitasking was all I knew. Some days, I thought I was slightly insane because of what I was able to do and keep track of, all at the same time.
But when it comes down to working my creative and strategic brain, I cannot have distraction. I thought I'd be good at multitasking but NOPE.
Maybe you’ve experienced this before. On days when you have a million things to juggle, you get to the end and look back like “what did I even get done?”
But days when you silence all notifications and allow yourself to go into deep work, you’re blown away with what gets accomplished.
The difference between the two is insane. So while I initially thought multitasking would be a huge strength for me, I was quickly proven wrong.
Three. People WANT story
Honestly, if I knew this sooner I probably would have felt more confident about what I was doing from the beginning because I LIVE FOR THIS SHIT.
In fact, if you’re new around these parts, I’ve got a free guide to help you start infusing story into your emails.
I promise, it’s not as hard as you think 😊 → check it out.
Here’s the deal: our brains are wired for story. It’s how we learn, make sense of the world, remember important details (way better than memorization. Just give it context and meaning and BOOM, it’s in your brain)... so when I realized that story could not only be worked into my copy, but that it actually gave it more power, I was hooked.
So as I began to write more (for clients and for myself), I focused on getting storytelling into every aspect of my copy as I could. If you want to create connections with your audience and help them relate to you on a more personal level, don’t wait to realize this for yourself. Get on it!
Four. Shit’s lonely
As an introvert, I thought this whole work from home thing would be a DREAM. And 99% of the time, it is. It’s quiet, I can do my own thing, I talk to people via Slack, text, email, etc. I don’t have to deal with loud noises and screaming children… It’s gold. But even as an introvert, I find myself getting lonely.
Definitely didn't expect that.
There’s a certain aspect of socialization we get from a more traditional workplace than what we can get from remote work life. Virtual connections are great, but it’s not the same.
And you’re also doing a lot yourself too- all of the tasks in your biz, working longer hours (while promising yourself you’ll get better at work-life balance. Guilty.), maybe even unintentionally distancing yourself from others because you feel like you have to focus more on your biz. If you don’t do it, who will?
Close the damn computer and get away from the work. My mental health and soul needed it, and I’m positive it would do you good too.
Five. Insecurity is reaaalll
Imposter Syndrome is a bitch. And as much as I work really hard to push through it, it still prevents me from doing a lot of what I want to do.
When you’re so used to doing something for so long (I was a teacher for 9 years before I said BYE!), it’s hard to jump into something new. We’re used to just knowing things and as an adult and we don’t often put ourselves into that “beginner” role again.
Yet by jumping out of the 9-5 and into freelance copywriting/entrepreneurship, I literally threw everything I knew out the window… and struggled hard.
Something that really helps me now is making things NOT about me. I got into this because I want to help others. And while I hated teaching in public schools, I DO like teaching and helping others become better at what they set out to do.
When I make it about YOU instead of ME, it becomes easier to do things. It wouldn’t be very nice if I just kept all my knowledge and experience to myself, right?
Sure, I STILL doubt every single blog post I write, thinking who the hell wants to even read this?! Yet I still do it, because even if it only helps one person, that’s a win in my book.
So if you’re struggling with Imposter Syndrome too, give that mindset shift a try. Instead of thinking things like, “what are they going to think of me? What if I look stupid?”
Remember, they’re thinking about themselves, and want to know how you can help them. Make it about them and put your magic into the world.
Six. Networking and community is everything
It can be hard for me to put myself out there. Then remove social settings and put everything online and it’s even harder (see introvert, loneliness above 😅).
Seeking groups, mentors, and fellow entrepreneurs has been a game changer. If I have questions, I can talk to people who are going through the same thing. Or I can give my insight to those asking questions I know a thing or two about. And I can be reassured that we’re all struggling and figuring out this shit together… and that we’re really not alone.
Plus you’ve got built in support, accountability, opportunities for collaboration… the possibilities really are endless.
When I get into a social mood, I can comment, message, converse with many people and build connections… and when I get a million notifications as their responses all trickle in, I can have my brief moment of “oh shit what have I done!” But then I take a deep breath and tackle them in small chunks.
Seven. Evolution is inevitable
As a multi-passionate person, I just love learning and doing SO MUCH. And I’m not going to lie, figuring out what I want to do and staying focused on building up that one path is hard for me sometimes.
People often talk about this idea of chasing the next shiny object for their biz but for me, it’s not that. It’s that I’m seriously passionate about so many things and I would love to share it with others!
Spreading myself too thin will just result in nothing being done well. BUT I’ve also realized that what I’m doing now doesn’t have to, and most likely won’t be, my biz forever. I’m allowed to change and grow and it’s okay if I decide to pivot at some point. That takes a lot of pressure off of my shoulders, knowing growth is going to happen and change might result from that growth.
Eight. Perfectionism can be a curse
It can be SO easy to get held up on waiting to do something, post something, write something, etc. until you have it down perfect. I know because I’m that way. I can’t say “used to be that way” because there are still things I struggle with that I KNOW I’m letting perfectionism be my excuse for (ahem, Instagram, I’m looking at you).
The thing is, I quickly learned that if I wanted to start making changes in my life, I couldn't wait to feel 100% comfortable or confident in what I was doing. I just had to do it.
And while that was is so hard for me, the thought of staying stuck and not allowing myself to reach my true potential was harder.
I’ve heard so many versions of the same concept:
Done is better than perfect
Take imperfect action
Action creates clarity
And they all stem from the same thought. Just do the damn thing. Waiting to feel 100% ready or waiting for everything to be “perfect” is just an excuse at this point. Definitely a mindset shift I wasn’t ready for.
Nine. Rest is necessary
Silly me thought I’d be able to manage my time perfectly from the get-go but here I am trying to do MORE because i have “more time” 😅 I may not be doing physical labor or feeling mentally exhausted from my job anymore… but burnout can still happen.
There are days I hate my laptop and want to throw it across the room (figuratively)... and when I look back, I realize I’ve been on it all day for my contract position and all afternoon/evening working on biz stuff… for DAYS in a row. Hmm… maybe it’s time to rest, Jess.
It might seem like it’s better to power through but taking frequent breaks throughout the day helps keep me focused and doing my best work.
And then making time for longer periods of rest and making sure I’m not on my laptop every single evening is also very important.
During those times, I try so hard to do things for ME. True relaxation… Not sneaking in another educational video on YouTube.
Ten. It’s now my job to learn
I mean a few things when I say this.
First, things in the tech world are always changing so I need to stay up-to-date on anything that involves what I’m doing online. Definitely didn’t realize how rapidly things shift around these parts with digital trends and whatnot. It’s a bit exhausting.
Second, I always need to be tuned in to my audience and see their struggles… and then take the time to learn about and understand what they're going through. I need to make sure what I’m doing is aligned with what they need. If I truly wish to serve people and help them in areas they really need help with, then it’s important I take a step back, listen to them, and learn. There’s definitely no room to be a know-it-all here!
Third, if I’m going to put myself out into the digital world to teach and help others, I need to make sure I’m always giving the best info I can. This includes topics like copywriting strategies, tips, and best practices, marketing approaches, mindset shifts… anything that helps me as an entrepreneur but would also help you. To sit and talk about outdated thinking would just be doing you a disservice, I need to constantly be reading, doing, learning, reflecting, thinking, etc. so I can share what I know and do with you in the best way possible.
If there’s anything I learned from my shift into this new identity as an entrepreneur, it’s this: you can’t ever truly be prepared. Putting in the time, energy, and effort into my biz is what has helped me feel more confident, but that confidence couldn’t have come beforehand.
As I said before, would knowing these things ahead of time stopped me from jumping in and pursuing this dream of mine? Hell no! But it’s nice to not be blindsided by things you never even considered, you know?
What things do you wish you knew before YOU started your biz and became an entrepreneur?
Did anything catch you off guard?
And hey, if you’re looking for random, thought-provoking stories that connect with these ideas… you know, the inside scoop I don’t just share with anyone, get on my email list!
Along with being entertaining and insightful, each email is like an example on storytelling in action 😉
