The First 5 Things I’d Do if I Were Starting My Business Over Today


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A habit that has woven itself through many facets of my life, like parenthood, my health, and entrepreneurship, is a consistent check-in I like to do with how I’m growing.

I often call it a ‘life inventory’ where I scoop up everything I’m working on, learning, and feeling, and ask myself about what’s going well and what needs to shift.

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Inevitably, I spend a little bit of my check-in time wandering back down memory lane to the beginning stages of starting my business. With over a decade’s worth of experience, successes, trials, and a whole lot of teachable moments, it’s normal to wonder what I might’ve done differently if I knew then what I know now.

While I could wax poetic about all the things I wish I could share with my 20-something self, the advice I would give for starting my business is rather simple.

‘Keeping it simple’ might be the best way to summarize what I’ve learned about almost everything in life. So, take a step back with me to those early days while I share what I’d do first, without overthinking, if I was starting my business over today.

Maybe you’re looking for a fresh start in your business or a little insight from a seasoned entrepreneur as you start on your own business journey. I hope this advice helps not only give you that clearer starting line you’re looking for but also combats that pressure to start perfectly.

I know you want to mitigate risk and avoid as many pitfalls as possible. But the learning curve is part of the journey. In the meantime, let these five insights guide your vision and keep that process as light, fun, and adventurous as possible!

The First Things I’d Do If Starting My Business Over

1. Start an email list.

Starting an email list has to be my first piece of advice for you because I cannot count how often I’ve guided new business owners and entrepreneurs to do this over the years.

I learned how much easier growing a business can be when you don’t have to count on platforms you don’t own and can’t control to deliver your valuable messages to the people you’re creating for.

While social media is important it can also be a space where you waste time, money, and creative energy trying to engage your audience that lives on the other side of a strict, ever-changing social media algorithm.

My advice? Start an email list as soon as possible before any of those resources are spent in places that won’t deliver tangible results. A nurtured email list means you’re showing up in the inboxes of people who want to hear from you, buy from you, and stick around for your stories and growth.

On social media, they might tap that follow button, but from there, they might not see your content for weeks, months, or even years.

And unlike your social media pages, your email list isn’t one hacking incident away from being totally erased, it’s an asset that you own. That’s a powerful difference from what any other platform can offer you online.

As you create new offers (paid or free), you’re able to see if what you’re serving up is irresistible enough for people to want to exchange their email addresses for it. As a new business owner, this is an easy, free way to start gauging what your audience wants most from you.

2. Find a mentor.

Mentorship can feel like a big move for a new business owner … with an even bigger price tag. We crave answers and guidance in the beginning, but usually with a beginner budget, we tend to keep mentorship on the back burner.

I spent a little too much time piecing together my own plan out of stubbornness and feeling like I needed to earn all my advice.

But, as someone who eventually would become a mentor to many, I realized how much mentors want to give their advice to newbies! And not all mentorship needs to be one-on-one or costly. There are mentorship opportunities all around us if we know where to look.

First, look for free learning pathways. Tune into a podcast, like Goal Digger, my business and marketing podcast, where I share not only what I’m learning in business but open up conversations with amazing thought leaders, entrepreneurs, and visionaries to pull out their insight, too.

Plus, I even drop episodes that are live mentorship and coaching sessions with all kinds of people who are at their own starting lines or turning points in business.

Learning from other leaders who inspire you can also be as easy as taking a digital course. They can teach you through their course that can come at a more accessible price point while delivering their brilliance right to your screen.

Find someone who’s gone before you and is doing something similar to what you want to do or how you want to do it. Look for people who align with the kind of business owner you want to become. If they have a course, take it. If they have a book, read it. If they host live classes or have an online community, grab a seat.

Eventually, whenever you’re ready, you might even go out on a limb and ask them to mentor you in whatever capacity they can. You might just land your dream mentor!

3. Share your focus and goals.

This can be a tough part of starting a business because the pressure to be impressive or show off our success can keep us from showing the building process.

The journey doesn’t always look ‘pretty’, and it can be tempting to hide those parts (like when we clean up our entire house before the house cleaner comes over.)

But looking back, I regret those moments when I hid my learning process, waiting for everything to be ‘perfect,’ keeping me from growth because when is anything ever perfect? Letting people in on my journey is when my business completely shifted and growth started building in huge waves.

My audience responded to these seemingly messy or incomplete glimpses into my process with a resounding “This is so real!” We related on a whole new level and more people wanted to work with me, trust me as a client, and buy into my new offers.

Beyond ‘being relatable’, here’s why sharing your process and focus is so effective: you want your offers to make sense to the people you’re making them for. The only way they’re going to get the clearest picture of your offer is to let them in long before you finally share the ‘tada!’ moment.

Surprise drives way less results than anticipation. Show your people what you’re working on and allow them to support and champion you!

4. Get clear on your brand vision.

Starting your business is already a massively pride-worthy moment.

I was so proud to finally get out of my corporate, windowless office and launch into my career as a photographer and then as a digital marketer, but what I needed to get grounded with was my brand. Early on, I genuinely didn’t know the difference between my business and my brand.

An easy way to boil it down is that your business is simply your offer. It’s the solution you give your clients, the service you sell, the products you produce! But your brand is your personality behind every offer, service, and product. Sure, Audi makes cars, but how a person sells them makes all the difference, right?

From your social media, your website, your ads, your blogs, and everywhere else you show up online, your personality should be visible. Don’t hide behind your offers or think that they speak for themselves.

In fact, you’re their best advocate. Your excitement and confidence in what you’ve created is what resonates with your audience!

Your personality can show up long before you even have something to sell. Think about how you show up on social media.

  • Do you know why you’re posting or creating?
  • When you take a step back, is your brand vision clear with everything you post?
  • Can you see your own unique perspective, flavor, and approach woven into your captions and images?

If you’re struggling here, I’ve coined a social content approach called the JK5 that might help keep your creative flow simple.

Every time you go to create a post, choose one from your five unique content pillars that guide your content creation and show your brand personality to your followers. It could be parenthood, pets, style, interior design, poetry, or anything that shows who YOU are!

If you want to learn more about the JK5 and your brand pillars, listen to this episode of my podcast!

Starting business over graphic with the JK Five for brand pillars

5. Choose your tools wisely.

I learned this analogy through my experience as a photographer, juggling a variety of lenses in my camera bag. I felt this pressure when I was just starting out to have every single lens for every possible scenario.

As my business grew, I bought new lenses but learned that there were just a few that I would reach for over and over again. I didn’t need all the shiny tools right away, and in many cases, never needed them at all.

When you’re just starting your business, you’ll probably be inundated by all the options for the best tools and platforms out there. It’ll make your head spin.

But most of them aren’t necessary for what you need on day one. You don’t have to spend your time and money merely looking like a business when that could easily distract you from being able to do the real work.

Take a few steps back and analyze what your biggest needs are. Differentiate between the ‘nice to haves’ and the ‘need to haves’ to keep your growth moving forward.

A key to helping yourself know the difference is by looking at the tasks that are already on your to-do list vs the ones that you’re looking forward to doing in the future.

For instance, you might need to invest in accounting software before the bells and whistles for your website. In fact, I’ll fully admit that I didn’t have a real branded, designer-made logo until THIS year.

You can go farther than you ever imagined with much less than you think!

Honor Your Own Journey

Overall, the biggest surprise to me is that I don’t actually want to redo any of it.

As someone who takes so much joy in the learning process itself, it’s only through the hiccups, the guesses, the mistakes, and the early days that I was able to awaken the unrelenting life-long learner and educator in me.

My learning journey is the only reason I can have hindsight enough to meet people at their starting lines or messy middles and be able to help them skip some of the confusion. I love helping smooth out the starting lines.

You’re so much more capable of amazing things than you might know, so any chance I get to help people like you get there is a joy.

So, while these are in some ways insights born out of moments of ‘regret,’ I would say I have a much greater appreciation for them as transformative experiences.

Honor your own flubs and challenges along the way! They’ve not only helped YOU become who you are and the skills you carry, but they’re also a pathway for you to help others make it through the mess as we’re all out here just trying to figure it out as we go.



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