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5 Lessons from 5 Years as a Business Owner

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There are certain milestones every business has, like special anniversaries in a marriage that require special gifts — paper, silver, gold! People say if you make it to 1 year, you’re set… or at least, that’s what I always heard. I feel like that’s true and there are other milestones to pass. Your first 6-figure year. Your first “oh shoot, I need a lawyer” situation. Your last “taking them just for the money” client. I recently passed 5 years as a full time business owner and I have hit all of those milestones and then some.

I posted about the date on Instagram and asked if anyone would be interested in a blog post talking about what I’ve learned in these 5 years of business ownership and got an overwhelming “YES!” response. Hopefully this helps you navigate your earlier years in business (or renews your love for your business if you’ve been around for a while, too).

1 – Organize Everything

I love a good to-do list. I also love containers and having everything in its place. At the same time, I can also let the mess balloon around me. However I always know where things are. Oh, my checkbook? Look under the pile of scratch paper near my blue-light blocking glasses. And that’s the point. Organize things so you know where they are.

Have a Dedicated Space to Work

Listen, I don’t care if you think you can work well in front of the TV with your feet up on the coffee table and some show that you’ve seen a thousand times already on for background noise. I guarantee you can’t work well like that.

We’re sold this laptop lifestyle where you can work from anywhere. And that’s true. But sometimes you need to really focus without distractions. You also need to be able to walk away at the end of the day. Otherwise, you’ll just keep working because there’s no distinct difference between “work” time and “life” time.

Having a dedicated spot to work will help you concentrate and it’ll also help you separate work time and life time. You can close the door to your office or move your laptop off the corner of the dining room table and practice “Out of sight, out of mind” so not every moment is dedicated to work.

Invest in Systems and Processes and Get Them in Order Before you Need Them

I spent way too much time trying to bootstrap things together with duct tape and bubble gum. Sometimes that works in a pinch. But sometimes that also means it’s hella frustrating to create these workarounds to save a buck or two when you could just grab a monthly subscription that does exactly what you need it to do.

Same with having a routine or a set workflow of doing something. Take the time to set it up on the front end when you aren’t super busy so you save yourself time and energy (and maybe even avoid an expensive mistake) when you get into the heart of working on your business.

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2 – Find What Works For You

I tend to get stuck in a loop where I feel like I need to have the exact right system and process from the jump and it can never be updated. That’s so ridiculous. The likelihood that we’ll have the right answer the first time…all the time…is a bit like saying you’ll never eat a disappointing cookie. Cookies should be awesome, yet some just aren’t great. But you don’t know that until you try it.

Finding what works for you and being open to experimenting as you go is necessary. But beware, it’s a fine line between “finding a new tool” and getting stuck in analysis paralysis. Just pick something and make the best of it for now.

Tools and Processes that Work for Me

Pen and paper! I spent a lot of time feeling bad that I wasn’t using Asana / ClickUp / Trello for my business. It’s what we “should” use and what’s always recommended!!

That said, when it comes to tech tools, I have a few ride-or-die ones that I use for me (there are others that I use when I work with teams, which I’ve talked about here as well as a few other tools I’ve used). 

I recommend Dubsado to house contracts, forms, and schedulers. I know others prefer HoneyBook or 17Hats to manage client information. I thought about switching, but for now, this is fine. Wave sends my invoices and tracks my expenses, although I have a client who is all about QuickBooks, so I imagine it’s only a matter of time until I switch, too.

UberSuggest + Pinterest is also my favorite way to do keyword research for blog posts. CoSchedule is so helpful, especially to continue promoting links to your content after your blog post is published. I don’t use a social media scheduler now, but I have used Buffer, HootSuite, Tailwind, and CoSchedule at various times to manage publishing to social.

Work With Your Energy

Knowing your energy is so important. I know I am more creative and work best at the beginning of the day and also at the beginning of the week, so I set up my days to allow me to do my client fulfillment and other creative work when I’m the most sharp and can get the best result.

I also know I prefer to workout in the morning. Usually, I feel good afterwards and have really good writing sessions. So I will usually start my day in the same way (dog walk, work out, breakfast, writing). I’ve tried to write or focus in the afternoon or evening and nothing very good comes from it. Unless I’m on a deadline, I don’t push my creativity to try to be amazing at 4pm on Friday.

Charge What Works For You

Knowing your numbers is a big lesson I learned. I was working hard yet barely making anything. Everyone says to just raise your rates…but to what? Pricing is always a big conversation, especially for people just starting out and/or getting serious about making a sustainable profit.

Notice I didn’t say charge what you’re worth. I don’t think that’s helpful and it makes you feel like shit when no one takes you up on investing in a brand designer who’s just starting out yet charging $600,000 per hour.

When you do a job for a lower amount than what you need to sustain your lifestyle, you run into resentment for the project and/or client, you risk doing half-assed work, and you may even burn yourself out working overtime to make the money you need.

My favorite tip is to add up all your bills and obligations and that’s your “can’t make below this or I’m effed” number. That’s your baseline and you can go up from there. For example: Want to work with a coach who charges $2,000/month? Add it to your tally.

Eventually, you’ll get to a place where you have a good, better, best figure for your income. Then, you can look at your availability and decide how many people you have to work with to hit that number. Adjust as needed until you find a number that matches for you. Of course, pricing goes a bit deeper than this, but it’s a start.

3 – Know That It’s Okay to Change Your Mind

I think something that happens is that it’s seen as “bad” to change your mind. Right now in our society, changing your mind when presented with new information is seen as flaky, flip flopping, inconsistent, and so on.

Normalize Changing Your Mind When Presented with New Information

Surely, you’ve seen the memes on Instagram that say “Normalize Changing Your Mind When Presented with New Information.” I am here for it! As someone who can get stuck in that analysis paralysis loop trying to pick “the right thing” or perfect answer from the very beginning, I remind myself of this concept a lot.

There’s nothing wrong with trying something, then moving on when you find a solution that fits more fully where you are in business/life. For example, I started by sending invoices through an Excel spreadsheet and collecting payment with a check. Then I found FreshBooks, then I decided that Wave was actually the right accounting tool for me. Same with how I send contracts.

Will it change again in the future? Yes. But knowing what your requirements are, picking something to meet yourself where you are now, and working with that until it doesn’t work anymore will help you to just get started. It’ll take the pressure off and normalize that act of trying something new. 

Release People That Don’t Fit

We’re always evolving and so it should be okay that what works then versus now evolves, too. As such, the people you surround yourself with will ebb and flow as you grow. You may outgrow your business coach or your favorite client is a good person, but they don’t fit with your new services yet you feel obligated to work with them.

When things, people, and situations become more of a drag than a joy, being open to releasing them (kindly, gently, in integrity and alignment with your values) is helpful for your mental health. Someone better will come in and fill that spot because the Universe hates a vacuum and will plop something in that hole eventually.

4 – Protect Your Energy

The lessons I’ve learned around energy management are probably the most important ones and the ones I A) Got the most questions about and B) Always feel are the most necessary pieces to work on in order to create a business you want to have and live with and work on.

Release the Shoulds, Comparison, and Pressure, Especially with Social Media

If we were talking in terms of a Facebook relationship status, my feelings about social media would fall squarely into the “It’s complicated” camp. I’ve been most active on Instagram lately. But I also have a Facebook Page and thought I’d try my hand at running a group. If it were a plant, it would be so neglected, you’d just find a shriveled stem and some dusty soil that’s pulled away from the walls of the pot.

I spent a lot of time doing what others were doing. I’ve also hired marketing strategists to help me create a plan for my accounts… And then did nothing with that plan. Part of me is jaded. Listen, I know what you’re doing when you like a bunch of photos in a row, follow me, then leave me a comment or DM me about my most recent photo.

Bottom line: I invested a lot of energy into a “should” version of social media. I also invested a lot of time in making myself feel bad that I wasn’t sticking to a plan or I didn’t have the amazingly branded accounts of some people.

What really helped (but also took forever to learn) was releasing that comparison and how “other” people do it “better”. Once I let go of that belief that “I should do it like X does” and embraced a way that I do it and a way that feels good for me, the relationship got better.

I mean, I still won’t do that like-like-like-comment shuffle, but I pay more attention to being genuinely thoughtful with how to interact with social media. And I think that pays off. Formatting relationships isn’t strategic. It’s what we as humans do.

Take Time Off

This past year has been challenging for time off. Society tells us to hustle and grind anyway then you add on top of that the fact that we were all home and productivity was glorified. I mean, how many memes did you see that were like “If you didn’t come out of lockdown with a new business and a new language learned, what were you doing??” Um, surviving, sir.

Like I said above, I try to notice my energy and schedule time off or slower work times for when I know my energy dips. Summertime, end of the week/month, etc. I also hold pretty firm to weekends. I know it’s important for me to have this downtime or else. Personally, I know I’m much better working in moderation rather than cutting things out entirely. So I try to be moderate in my energy. Otherwise, I know if I binge on work and go for 14 days in a row, it’ll take me as long to get my energy back up.

Humans weren’t designed to stare at a computer for 16 hours a day, 7 days a week. Experiment with how it feels to take a half day off every week, or a week off every month. It may take a while to discover what works for you, but I’d encourage you to do so.

Get Help

No one exists in a vacuum. Throughout my time in business, I’ve hired coaches for general business help and specialists to address one specific area of business. I’ve worked with subcontractors to assist me with writing when my load got too heavy to carry alone. I sought out a therapist to support my mental health overall. I’ve also made countless coffee dates, co-working sessions, catch up Zoom calls, and Voxers venting to business besties.

Once more for the people late to class. We cannot do it alone. And no one is asking us to. But in this system that values “being self-made,” I know I have to be very careful that my naturally independent streak doesn’t cross over into martyr territory. If that’s you, too, I can tell you that investing in help has always generated something positive for me, whether it was more money, more time, or more happiness.

5 – A Few Random Thoughts

Anyone else get to the end of a list and thinks, “I have so much more to say!!” Yeah. Here are a few ‘sound bites’ of tips that feel important to include.

Rushing Will Get You Nowhere

The workout I do focuses on fatiguing your muscles through slow, repetitive movements. You haven’t done a lunge until you try to only do 3 reps in 45 seconds. Just the other day, the instructor leading the class said, “Rushing won’t make the clock go any faster.”

Embracing where you are now and being in the moment is hard, y’all. But it’s a good practice to get into. When I do rush and try to go faster and further and think 5 steps ahead, it’s inevitable that something goes wrong that makes me double back or re-do something, thereby wasting more time. That is not the way to go. When I feel like I’m in those grips of anxiety with time and pressure, I remind myself that time will go just as fast as it’s going to go. Rushing won’t help anything.

Know Where You Want to Go

One of my clients was a coach who also sold a vision board kit. In my time writing for her, I learned so much about the power of a strong vision. If where you are now doesn’t match where you want to end up, hold that vision for yourself and keep working toward it. Progress and taking the next right step toward that is more helpful than wishing for a big, “overnight success” type of change to take you from here to there.

What Goes Up Must Come Down

One of the hardest things to manage as an entrepreneur or business owner is the ebb and flow of it all. I don’t know about you, but I always want to feel progress and growth. To me, that used to look like things were always better. More in the bank account, more clients, more sales calls.

In time, I’ve learned that “better” actually looks like doing things with more intention. Or just doing things a little bit more in integrity with your values and wishes than you did yesterday.

That’s why I think it’s important to know where you want to go and do things for yourself, not for others. Embracing this rollercoaster of entrepreneurship is to be okay with the peaks and valleys. To know what you’re building and believe in it. Even if your actual business changes, it’s likely that your values will stay consistent. Make decisions based on your values and you will ride out the valleys and feel more joyful on the peaks.

Always Keep Learning

I feel like entrepreneurs are so good at this. We’re always learning through other people, whether it’s from coaches, masterminds, podcasts, books, etc. Our own bodies and intuition also house a host of knowledge. Staying curious, being open to ideas, and growing with that knowledge has helped me pivot and work through these last 5 years.


While this felt like an extensive post (congrats for making it through!) I feel like I just scratched the surface. There are always new lessons or bits of advice that I pick up as I go along. 

Are you an entrepreneur (solo-preneur, creative-preneur, soul-preneur…any-preneur) or business owner? What tips have you learned throughout your time working for yourself? I’d love to hear about them in the comments or share with me on Instagram or email me!

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angelica ross

Hey, friend! I’m Angelica.

Let’s create copy that’s relatable, fun, and reaches the people who need to hear it! I help bold, brazen, change-making entrepreneurs tell their story and write copy + content that’s as true and powerful as possible. And since cookie cutters should stay firmly in the kitchen (or wherever it is you like to bake), the work we do together will be as unique as you — but it’ll still create a powerful connection with your audience! Learn more about what we can do together!

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