5 Questions to Ask Yourself Before You Start Your Own Business
So, you’re thinking about starting your own business?
Exciting. Scary. A little bit both, right?
When I started my own business back in COVID, I didn’t really think much about it at all. I just knew I wanted freedom, so I jumped in headfirst.
Looking back, it worked out — but when people ask me now, “What should I think about before I start?” these are the five questions I always share.
They’re not complicated, but they will make your path a lot smoother. And by the time you’ve answered them for yourself, you’ll feel much more prepared to take this step with clarity and confidence.
So, let’s dive in.
1. What’s your why?
I know, I know — you’ve probably heard this one before. But even years into my business, I still believe it’s the most important thing to know for yourself.
Here’s why: having your own business is one of the most fun things you can do, but it’s also one of the hardest. There will be moments you want to throw in the towel. There will be moments you wonder why you’re doing this at all. Having a strong reason is what will carry you through.
For me, that reason has always been freedom.
I still remember hiking the Camino trail in Spain. Most people spend six to eight weeks walking the whole way. I only had three weeks off from work — the maximum I could get. I kept asking people, “How can you walk the whole thing?” And their answer was always the same: “I have my own business.”
That was it for me. I wanted that freedom. To travel, to work from anywhere, to decide for myself.
And honestly? That’s what kept me going in the early months. Even when things felt uncertain, there was no way I was going back to a 9-to-5. The vision of freedom was too strong.
So ask yourself: what’s your why? Because when the excitement fades and the hard days come, that deeper reason is what will keep you moving.
2. How do you feel about sales?
When I first started my business, I honestly didn’t even think about sales. I worked with my first client, the project ended… and I had no idea where to find the next one.
That’s when it hit me hard: Until then, I thought running a business would just be doing the work I loved. The actual “thing” I was good at. I didn’t understand that, in the beginning, the biggest part of your job isn’t the work itself. It’s finding the people who want to hire you.
And I’ll be honest: I lost sleep over it. Nights lying awake, worrying what would happen if no one else showed up.
If I had really thought about sales before I started, I might not have even taken the leap. And honestly, I’m glad I didn’t — because yes, sales was my biggest struggle at first, but it also turned into the thing I care most about helping women with today.
So before you jump in, ask yourself: how do I feel about selling? Am I willing to learn? And where might my first clients actually come from?
Because here’s the truth: if you want to do the work you love, you first need to figure out how to connect with the people who need it.
3. Are you willing to do the inner work?
You’ve probably heard the phrase inner work before. But what does it actually mean when you’re starting a business?
It’s the stuff no one sees: regulating your emotions when you’re stressed, picking yourself up after a tough day, calming the voice in your head that says you’re behind, and leading yourself through uncertainty when there’s no boss or team telling you what to do.
For me, this was such a surprise. I’d been great at my corporate job — always on top of things, always moving fast. And then, in my own business, I felt like I needed baby steps for everything. I was coaching myself all day long: reminding myself it’s okay, slowing down my breath, pushing through scary moments of showing up.
Truth is, business really is at least 80% inner work. Strategies are easy to find. But without the capacity to lead yourself through the messy parts, you won’t actually use them.
So ask yourself: am I ready for that? Am I willing to do the daily inner work it takes to lead myself?
4. Do you have a support system?
Here’s something I didn’t fully expect: starting a business can feel lonely.
Unless someone has their own business, they’ll likely not get what you’re going through. It’s not that they don’t care — it’s just a different world. That’s why, from the very beginning, I worked with coaches and mentors. Later, I also found a few ‘business buddies’ on the same journey. That mix, guidance from mentors and connection with others building their businesses too, made all the difference.
But support isn’t only about business. It also matters to have family and friends who love you no matter what, who remind you you’re more than your business, and who pull you out for a walk when you’ve been glued to your laptop all day.
Because yes, you will spend hours alone in front of your computer wondering if you’re making the right decisions. Having people who get it to celebrate the small wins with — like your first email subscriber who isn’t your mom — and people who ground you outside of it is what makes this whole journey lighter.
So before you jump in, ask yourself: who’s in my corner?
5. What do you need so you can sleep at night?
Here’s something most people don’t think about until they’re already in it:
leaving a steady paycheck changes how safe you feel.
When I first started my business, I was actually making more money than I ever had before. And still, I’d lie awake at night worrying I didn’t have enough. That monthly paycheck I was used to did more than cover the bills — it gave me peace of mind. Without it, even with plenty of money in the bank, my body still felt on edge.
Because that’s what this is really about: not the number in your account, but whether you feel calm enough to actually rest at night.
I know plenty of millionaires who still can’t rest because they don’t feel stable without predictable income.
There’s absolutely no shame in creating a baseline for yourself. For some, that’s a savings buffer. For others, it’s keeping a part-time job while they build. Whatever gives you that steady ground to breathe and sleep at night.
Because it’s so much easier to grow a business when you’re not panicking about money, but building from a place of calm.
So ask yourself: what do I need in place to feel calm and steady while I build?
If there’s one thing I hope you take away from this, it’s that having your own business is as much inner work as outer work. The more you can lead and coach yourself, the easier it becomes to do the things that actually move the needle.
It’s not always simple. There will be learning curves and messy days. But if you know that going in, you won’t be caught off guard — you’ll be prepared. And that preparation makes the whole journey lighter.
Because building your own business really can be one of the most beautiful and rewarding experiences of your life. And whatever your big why is — freedom, impact, creativity, or just more space to live life on your terms — you get to have that. It’s totally possible.
