Christina Tosi's top 7 tips for entrepreneurs on how to move forward when the startup phase ends

This scenario might sound familiar: You have an idea. An incredible, life-changing, one-of-a-kind business idea. Against all odds, you manage to bring it to life.

You figure out how to take your dream from concept to creation, how to write your business plan, build your team and bring in customers. Every day, you put in the work to get your new business off the ground.

Then, after countless late nights and coffee runs, you realize your business is in flight. You really have something here. You’re in your groove, you’ve found your product-market fit, customers are coming back…

And just like that, the honeymoon startup phase is over. Now, you're in what James Beard award-winning pastry chef and Milk Bar Founder/CEO Christina Tosi calls the “messy middle.”

Whether you’re two months or two decades into running your business, the messy middle tests every small business owner’s mettle eventually. And while entrepreneurs have resilience in spades, getting an extra dose of inspiration never hurt anyone.

Speaking of inspiration, Christina recently stopped by The Entrepreneur’s Studio to share her incredible story. From her bootstrapped beginning as a culinary student in NYC, to working for David Chang at Momofuku, to opening her first Milk Bar location in 2008 and beyond, Christina knows what it takes to stick with it and find your way forward when the confetti from the grand opening has settled and the messy middle begins.

Read on to discover Christina’s top seven tips:

Christina’s top 7 tips

1. Use passion as your guidepost

Most entrepreneurship journeys don’t follow a straight path. There are twists and turns along the way. Times when you feel like the sun is shining down just for you, and times when you feel lost in the dark.

Christina’s advice? Use passion as your guidepost.

“It's about putting your head down, following that passion, that heartbeat, that instinct in you.”- Christina Tosi

Following your passion doesn’t just mean finding that first big business idea. It means finding your purpose within your business every day after. If you aren’t sure what your passion is these days between the bills and the back office, Christina’s recommendation is to follow the breadcrumbs. Chances are your passion is manifesting itself in parts of your life whether you realize it or not.

Here’s what we mean: Are you always the first one to strike up a conversation with your guests? Do you find joy in teaching new hires about your business’ ethos? Constantly brainstorming ways to improve the customer experience? Do you get to the kitchen before anyone else to try out new recipes? Have the urge to snap photos of your business at all hours of the day to post to social media platforms? Find yourself researching new content marketing strategies?

Whatever it is you naturally gravitate towards, that’s your passion — the thing you were meant to do. As Christina put it: “You're not going to miss your destiny. You just won't, otherwise, it's not your destiny.”

Part two of Christina’s advice? Once you find your passion, do it with all your might. Doubt can be your biggest enemy. For Christina, it’s about making a choice to turn off the other voices (internal and external), trust your gut and use that instinct as your lantern in the night when the going gets tough.

2. Just bake the cake

Sometimes, even when you have your guideposts to look to, it can still feel like you’re stuck in quicksand — especially when it comes to initiating change at your business.

If you’ve been waiting for the perfect moment to open a second location, or add sustainability practices to your business model, maybe revise your operations … write a new marketing plan, update your menu with new items or your store with new products, launch your ecommerce site or finally do that rebrand … we have some not-so-fun news. That perfect moment is probably never going to come. And you’re probably never going to feel 100% ready.

The meaning behind the metaphor? There will always be a reason not to do something. There will always be a story you can tell yourself where waiting makes sense. But sometimes, you just have to start baking the cake — even though you don’t know how it will turn out.

“Don't go looking for that big break or big moment and just look at everything as one step forward, the opportunity to take one step forward.” - Christina Tosi

Been struggling with how to get out of a rut or take your business to the next level? Whether you have an intimidating business goal looming before you or you already accomplished it and are waiting for the next bout of inspiration to strike, try Christina’s strategy on for size and keep putting one foot in front of the other with an unshakable rip-off-the-band, just-do-it mentality. In Christina’s words, “You have to love just that cold, hard march into and forward when you can't see the future.”

You never know, today could be the day you look back on five years from now as the day everything changed for you, because you just baked the cake.

3. Learn to love rolling the boulder

So there’s this guy. And every day he rolls a boulder up a hill only for it to roll back down once he reaches the top, forcing him to do it all over again. Yep, we’re talking about the Greek myth of Sisyphus. Why? Well, as Christina says, sometimes running a business can be a bit like rolling that boulder.

As an entrepreneur, we’ll wager you love creating something new that doesn’t exist yet. But what about once it does exist? As you’ve likely found, the work of running a business — of keeping it going and growing — is a lot less riding high on flashes of excitement and a lot more showing up every day to do the work whether you feel like it or not.

While you’re not literally eternally rolling a boulder up a hill in the depths of Hades, sitting down once again to build schedules, field online customer reviews and calculate paychecks can have a way of feeling like it.

But if you ask Christina, learning to love that routine is just as essential to your business’ success as coming up with your next big idea. Want to build loyalty in your target market? Win over potential customers? Prove you’re reliable? Keep your customer base happy? Gain trust? All of the above require repetition and stability.

“You have to love the beauty of the daily routine of waking up every day with the commitment to build, not knowing what else it holds other than it needs you and you got to show up and do it no matter what.” - Christina Tosi

Doing the same work day in and day out consistently is really hard. But if you want your business to stand the test of time, finding the beauty in rolling the boulder up the hill is key.

4. Practice being uncomfortable

While committing to your routine is half the equation, Christina would say regularly getting out of your comfort zone is the other.

Here’s Christina’s strategy: Force yourself to do things that are uncomfortable for you every single day. Make it your goal to pack your schedule full of challenge and defy what you can do in a day. As Christina says, “I can't defy gravity. Gravity is a pretty set formula here on earth, but I like to defy what I can do in a day.”

We aren’t saying you need to go find the nearest open mic night and belt out a Whitney Houston song or sign up for skydiving. There’s no set template — you write your own rulebook. Practicing uncomfortability looks different for everyone.

Whether it’s showing up for a co-worker who’s having a hard time, reaching out to new customers, scheduling a difficult conversation or performance review with an employee, facing that spreadsheet you’ve been avoiding or communicating with customers about raising your prices, choosing to run toward that uncomfortable task instead of away from it will pay off in the long run.

“There are people who need to hear ‘Hey, it's hard. It hurts. And there's a different future if you don't stop.’" - Christina Tosi

Here’s another way to look at it: If you stay inside your bubble where everything’s safe and never step outside of that, your business can’t progress beyond that stage either. Being a leader who gets comfortable with being uncomfortable is one of the most powerful things you can do to catalyze long-term business success.

5. Don’t let failure be a surprise

You know how you’re supposed to taste your cooking throughout the whole process instead of waiting until the end only to find the seasoning is totally off? Same goes for your own business. You shouldn’t wait until something’s already gone wrong to check in with how your business is doing.

“Your business is a living, breathing thing. You have to keep your finger on the pulse of it. You have to always be thinking and open.” - Christina Tosi

When you’re caught up in the day-to-day of running a business, it can be all too easy to let the demands of your daily to-do list overshadow the bigger picture, to the point where you can’t see the forest for the trees.

Here’s what Christina does to stay on track: Check in with yourself frequently. Whether it’s a formal journal entry or an internal dialogue on your commute home, the important thing is to set aside time to zoom out and take stock at the end of the day.

Christina recommends asking yourself these questions: Did you leave this place better than you found it today? Are you happy with what you're doing? Are you driven? Are you proud of the work that you did today? What could you do better?

Building a habit of paying attention and having daily check-ins can make all the difference in maintaining a successful small business — and saving yourself from the surprise of failure.

6. Find people who share your values

We can all agree: Running a business is hard. And no one does it alone.

The success of your business depends on the people who are part of it. This is something that’s just as true for the messy middle as it is for the early stages — maybe even more so. As your business matures, you need people you can rely on to help analyze what you’ve created, think intentionally about who you are and what you’re about, solve more complex problems, find new paths to progress and maintain a profitable business environment built for long-term growth.

“I think the messy middle is real, and it's beautiful in all of its ways. But you have to stop and truly take stock of the business. And you have to say, ‘What is this thing? And what is our intention? What's our mission statement? What do we believe in? What are our core values?’” - Christina Tosi

After establishing your values, the next step is finding a way to communicate about your culture and share it with others in order to attract high-quality candidates who are good culture fits and have values that align with yours. With labor shortages to contend with, having a message people can connect with could help you stand out.

But it takes vulnerability. Christina said it best, “How do I figure out how to tear open my chest and take what's in my heart and show it to other people to say, ‘You in? Do you believe in these things too? Are you in?’”

For Christina, it’s a two-way street. By establishing your values and sharing them, you’re letting your employees know your expectations of them, but also your expectations of yourself. Essentially, they’re making a commitment to your business, but you’re also making a commitment to them. Building a team that shares your dream and has your trust means that relationship has to be a give and take.

7. Remember dessert can save the world

Picture this: A little girl is riding with her mom in the car. It’s an ordinary afternoon, nothing special to it. Then, out of nowhere, her mom pulls the car over. She reaches into her purse and pulls out a bag of Sugar Babies to share with the little girl. She doesn’t do it for any particular reason, other than celebrating the existence of dessert.

Fast forward, and that little girl is now the owner of Milk Bar.

What’s the moral of the story? That small moment changed Christina’s life. It put her on a trajectory to dedicate herself to bringing that same moment of joy to others through her passion for dessert. Since then, she’s changed countless other lives through the customers she’s fed, the people she’s brought into the Milk Bar team, the role she’s played in shaping the next generation of young bakers and so much more.

“I would venture to think that anyone that's on their entrepreneurial journey, that there's something about what they do that makes the world better, makes people's lives better. For me, dessert can save the world.” - Christina Tosi

When times are tough, think about what your “dessert” is. What’s that spark you bring to the world through your business that makes it just a little bit brighter? Your answer is your purpose, it’s the reason you do what you do. And believing in that, no matter what, is why you keep going — even when the middle gets messy.

Ready to embrace the messy middle?

As you know firsthand, running a small business isn’t easy. Along the way, there are mountains to climb and waves to ride. Flashes of pain and moments of celebration. All heartfelt, challenging and fueled by a passion that is only known in small business. But if you stick with it and keep going, what’s waiting for you is worth it. Just ask Christina.

New York-based bakery empire or hometown vintage clothing shop, whatever your thing is, you were made to do it and you have everything you need to keep going. If you’re having trouble finding your way through the messy middle of your small business journey, just look back at what you’ve accomplished so far. All your past work and life experiences have shaped you uniquely to be prepared for where you are right now.

While it’s tempting to view the early days through rose-colored lenses, don’t forget this is the exact moment you used to dream about when you were working so hard to get your business off the ground. If you haven’t already, it’s time to celebrate that you made it to the middle. Probably with a slice of cake.

Looking for more inspiration? Check out The Entrepreneur’s Studio to listen to more stories from entrepreneurs like you who have seen hard times, stuck in and found a way forward to something even better.

Disclaimer: All trademarks contained herein are the sole and exclusive property of their respective owners.

---

Heartland is the point of sale, payments and payroll solution of choice for entrepreneurs that need human-centered technology to sell more, keep customers coming back and spend less time in the back office. Nearly 1,000,000 businesses trust us to guide them through market changes and technology challenges, so they can stay competitive and focus on building remarkable businesses instead of managing the daily grind. Learn more at heartland.us