A Letter to My Former Self: 10 Things I Wish I’d Known When I Started My Small Business

Man writing letter about what I wish I'd known when starting my small business

Dear Past Self,

Hey there, hope this letter finds you and your home-based business well. Oh, wait. You haven’t got that going yet? Well, I’m reaching out because I need a favor here…I need you to start making moves. ASAP.

Listen, I’m not taking the time out to hash out old stuff, but it absolutely rips me apart to see my brilliant, intuitive, gifted, and incredibly good-looking self, playing small. That’s right, wrestling with burnout and overwhelm is not a good look for you (us). Neither are the bags under your eyes from the pressure to stay in your “normal job” because it’s safe. Starting a small business is scary, but you are at a critical “make it or break it” juncture in your career, and I’m here to tell you that it’s time to step into your fullest potential. I know you’re scared, but you know what’s scarier? Another 10 years reporting to that horrendous human being who runs the company you’re at.

There are brighter days ahead, babe. And this is kind of against the rules, but I’m going to give you some insider info that’ll get you going in the right direction. Every founder has a story about what they wish they would have known ahead of time. Alright, I know what you’re thinking (because I am you). Your “perfectionism” excuse is not going to work on me.

Take a seat because I’m about to blow your mind. Perfectionism leads to procrastination because we’re afraid of making mistakes, hence, not being perfect. Instead of failing, you’d rather play it safe and not do anything at all. These tendencies are holding you back from becoming the multidimensional, forward-living, innovative (and cute) business owner you’re meant to be. Let me take you on a little journey through time — these are the things I wish we knew before starting a small business.

Find Your Focus

Have I ever told you how innovative you are? Seriously, you have so many amazing ideas, genius doesn’t even come close. But starting a small business isn’t your greatest flex (not yet, at least). When you’re getting started, it’s quite normal to be all over the place, especially when your vision isn’t clear. And by vision, I mean your company’s mission (although you really do need to make that appointment to see the optometrist). Time to get back to the basics, boo. That means focusing on your one core product — get it made and out into the world. If that seems unrealistic, start removing parts/features/layers/frosting until you get to the product at the center of your home-based business. It’s great to think big, but being an entrepreneur requires a different set of thinking caps. Stay hyper-focused on serving the customers who want your product. Become a niche rock star and bring the house down.

Find Your Why

I already know the answer, but ask yourself something, “Why am I starting this small business?” Perhaps you have a product/service that the world needs, you want to make a positive impact on society, or you’re ready to be your own boss. No matter what the reason is, keep this at the forefront of everything you do because this will be what keeps you grounded. This will be the foundation for branding your business and creating marketing strategies. If you’re not sure what kind of business fulfills your “why,” there are tons of home-based business ideas out there.

Game Plan

In order to start playing with the big kids, you’ll need to cross your T’s and dot your I’s. Get your company started right by having all the legal structures and operational formalities outlined in a…business plan. *Gasp* I know, that might be the most terrifying word to a newbie starting a small business, but it needs to get done. A business plan is a document that details your future company’s objective and how you will go about achieving those goals. Basically, it’s a written road map that plans out how you’ll approach everything from marketing, financial, and operational, goals. It may feel overwhelming but take it step-by-step and think it through carefully. This will give you a lot of perspective on what kind of business you’ll be hustling.

Money Flow

A really smart person once said, “Girls just wanna have funds,” and I really felt that. As much as you are passionate about your cause and building a home-based business, you want to make as much cash as possible. Do we blame you? No. You work hard, and you deserve those funds. Your business plan should have a dedicated section to your finances to determine what it means to fund this thing. Bottom line, will you need to borrow money to start this small business? Should you consider crowdfunding? Will you need to stay at your full-time job before focusing on this venture full-time? When financial planning, be sure to perform a break-even analysis to determine when you will be profitable.

A Legit Business

When the time comes, you’ll want to make your business relationship official. How? Register with the government. Seriously, you are so cute together! Ha. You’ll need to acquire the appropriate business licenses, incorporation documents, tax forms, trademarks, as well as any other legal needs to take your love to the next level (so happy for you two).

 One Team, One Dream

Alright, sweetie. It’s time to get really honest with yourself and figure out…what you’re bad at. I know! This is going to be really hard for you (us), but the truth is—we are not perfect. *The horror* Just breathe, I know this is shocking news. The truth is, figuring out what your bad at is going to help with the entire process. That way, you can hire the right people who are good at those things. Think about it, you hate doing our finances right? Well, I happen to know some lovely folks at Alchemy Accounting who can take care of basically anything money related. Even if you plan to be a solopreneur, you’ll need professionals who can do your taxes, marketing, small business management, change your printer cartridge, deliver your vegan Caesar salad, etc. Hire to your weaknesses, because teamwork makes the dream work.

 Romaine Calm

Okay, first of all, remember to eat more veggies. I know my puns are cringe sometimes, but staying calm (and being able to crack a joke) makes all the difference. Why? Because starting a small business is going to be stressful. Don’t let the idea of stress impede you from following your dreams, but it won’t be as simple as clocking in and out each day. You’ll have to be ready to take on tasks that you aren’t used to — a little bit of graphic design, crunching the numbers, creating TikToks, refilling the coffee machine. From the jump, be honest with yourself that this is going to be a journey with lots of highs and lows. But at the end of the day, it’s going to be worth it. Surround yourself with other entrepreneurs or join an online group for people who are building a home-base business. Stress is natural and it’s nothing you can’t handle (I know, I was there).

Help Me, Help You

Speaking of online groups, there are tons of resources out there for solopreneurs like you/us. Most people who start a small business will find that those around them will be stoked to help out in the beginning — they’ll offer an introduction, a service, or access to their color printer. They love your ideas and sing you praises, attesting to your business savvy acumen and imminent success. However, when it comes down to calling in that favor, you’ll be disappointed to find out that people won’t always come through as promised. This isn’t a deterrent to ask for help because after all, it takes a village. The point is to keep your expectations real and trust the process. Good help is hard to find.


I know you have it in you (because I’m you and you are me, remember). I wish someone had told me that if you’re serious about starting a small business, there are going to be sacrifices. More than likely, you won’t be able to take that summer-long vacay eating bread and wine all over Europe. You’ll miss out on: Margarita Mondays, Taco Tuesdays, Wine Wednesdays, Thirsty Thursdays, Fireball Fridays, Sake Saturdays, and Sangria Sundays (sorry, love). Expect late nights, early mornings, and lunch at your desk. If it were easy, everyone would become an entrepreneur. Things might look a little different, but you’ll love your life so much you won’t even miss Wine Wednesdays. And eventually, when you’ve put in the hard work and scaled your business, you’ll be going to: Margarita Mondays, Taco Tuesdays, Wine Wednesdays, Thirsty Thursdays, Fireball Fridays, Sake Saturdays, and Sangria Sundays. And hey, you may even be able to order doubles.

Lesson Learned

Every single small business starter will tell you that they have made mistakes. No matter how much research you do, advice you take, planning you implement, cocktails you consume — you will make mistakes. There is no avoiding it and the point here is to embrace them. Don’t hold onto your failures so that you become paralyzed into moving forward. Learn from what happened, move on, and never make the same mistake again. Done and done.

Following a step-by-step guide to starting a small business might seem like the simple fix you need, but you’ll never be able to anticipate what will happen. Everything will unfold as it should. However, with your determination and pure will, there is no doubt that you will be successful and live your full potential. One more thing! I do have another piece of advice because I know you so well.

Remember when we talked about finding good help and building your dream team? Well, our friends over at Alchemy Accounting are a-m-a-z-e! You’ll find out later, but they will effortlessly manage your books so when tax time comes around, you won’t be scrambling around like you usually do (sorry to call you out, but it’s true). Reach out to them ASAP because your business will be booming sooner than later — and the only way to get started is to…well, get started. So, hop to it, young me! Keep your head up and don’t forget to make that appointment to see the optometrist. And call mom, she doesn’t use email.

Love always,

Your Future Self

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Michelle Cooper

Michelle Cooper is a powerhouse entrepreneur, CEO of Alchemy Accounting & Bookkeeping, author of Confessions of a Money Rock Star, Your MoneyDate Journal, and co-author of the collaborative book, Women Rising. She has helped many business owners climb out of entrepreneurial poverty into the land of profit.