From Beach Bags to Business Plans: 

3 Ways Entrepreneurship is Like Going On a Beach Vacation

Summer at the beach has become a tradition for my family. Every June we pack up and head to our beach house at the shore for the entire season!

While we look forward to this time away every year, beneath the surface of splashing in the ocean, long walks on the boardwalk, and evening ice cream trips a ton of preparation goes into making these wonderful beach memories possible and successful. 

Whether it’s a quick weekend getaway or an entire summer retreat like ours, prepping for the beach demands careful planning—just like running a creative business. 

From the days of hard work leading up to a trip to the moments of bliss once you’re there, and everything in between, the similarities between traveling to the beach and running a creative business are uncanny. 

If you’re a fellow creative entrepreneur, I bet you can relate!

Join me in this blog post as we dive into the 3 ways entrepreneurship resembles a beach vacation: the good, the challenging, and the beautifully chaotic so you can learn how to succeed in both.

# 1 Planning is Key

First and foremost, planning and overall organization are key components of both a beach vacation and entrepreneurship. 

Now, this definitely looks different from one person to the next, but the trick is finding what level of planning and organization works for you!

When getting ready for a trip, this might look like creating a packing list, mapping out an itinerary, or organizing items in a logical manner to make the trip much smoother and more enjoyable.

Similarly, in entrepreneurship, having a well-thought-out business plan and strategic systems in place can greatly increase the chances of success.

In both scenarios, you’ll want to approach planning in a way that fits your needs and lifestyle. 


Let’s dig in!

Identify your style

When planning a trip, before you make a single reservation you need to decide what kind of trip you want. 

Do you want an action-packed adventure or a laid-back time lounging on the beach with a good book? Maybe you’re looking for something in between? Remember, it’s your trip, so you get to call the shots!

Everyone’s version of a perfect beach day is different. 

I was reminded of this the other day while watching people flood the shore from my office window at our family beach house.

I couldn’t help but notice the variety of different beachgoers:

Some arrived with wagons filled to the brim with toys and beach gear, while others carried boom boxes and disc golf equipment. Then there were some people who strolled onto the boardwalk with nothing but themselves, their flip flops, and a juicy beach read.

It dawned on me that everyone’s idea of a perfect beach day is uniquely their own, just as everyone’s vision of a perfect business is different.

When identifying your style as an entrepreneur, you’ll want to get some clarity about what you want out of the experience!

Are you driven by ambitious goals as a “success entrepreneur,” striving for professional and creative milestones? Or do you lean towards being a “lifestyle entrepreneur,” where your work supports your vision for your life and family? 

There’s no right answer, and your style can evolve over time as your priorities shift.

Get Clear On Your Destination + Goals

Simply put: when it comes to beach trips and business, make sure you actually want to go where you’re headed. 

Hate to break it to you, but all the planning in the world won’t mean a thing if you plan a vacation somewhere you didn’t even want to go in the first place. 

Likewise, if you build a business without really considering what you want your life and work to feel like, you may end up with an accidental business or a business that someone ELSE would love, but you dread! 

When planning a trip or building a business, deciding where you want to go comes down to getting clear on your definition of success. For some, a successful beach trip is about hitting all of the landmarks and seeing all of the sights. For others, success is doing absolutely NOTHING while sipping pina coladas on the beach. 

In business, some people define success by the number of zeros in their bank account, while others see success as having time-freedom to be present for their family or location-freedom that allows them to work from anywhere in the world!

You might define success in ALL of these ways over the course of your lifetime! 

Let your business be a reflection of your unique aspirations, not what you think you should be doing by everyone else’s standards.

Do your research!

With a clear vision of where you want to go, you can set a goal and plan with your destination in mind. The expression, “luck favors the prepared” comes to mind here. 

If you’re planning that beach vacation, this might involve scoping out activities and events in the area in coordination with the dates you plan to be in town. 

In your business this could look like doing market research to get in touch with your potential clients, seeing what others in your industry are doing for inspiration, or even planning for seasonal trends in your line of work.

For instance, with a little research and data analysis, you might notice that the majority of your orders come in during the holiday season. By planning your life and work schedule accordingly, you can anticipate the busy workload in fall and winter, while also carving out time to recharge in spring or summer (and even book that beach vacation we’ve been talking so much about!). It’s all about finding that balance, ensuring you’re prepared for peak periods while nurturing your well-being during quieter seasons.

#2 Flexibility & Adaptability Required

Going with the flow is a prerequisite for planning a trip to the beach and venturing into the world of entrepreneurship! 

If you’re a planner like me (ahem type A, recovering perfectionist) this may be a hard pill to swallow, but it’s true. Even the best-laid plans need to be taken with a grain of salt(water) beach pun intended. 

Your ability to bend, and not break, will often come down to these three things:


On vacation and in business, unexpected changes, delays, or new ideas can pop up at any moment. That’s why it’s crucial to maintain solid communication and keep everyone in the loop. 

Whether it’s booking that sunset cruise you’ve heard raving reviews about (before tickets sell out) or launching a new creative project, your people can only come along for the ride if they’re aware of what’s happening. 

Keeping the lines of communication open ensures everyone is on the same page!

Expect the unexpected 

Not only can things change, but they most certainly will. Vacations AND entrepreneurship often include the HIGHEST HIGHS and the LOWEST LOWS. There are always things outside of your control (like rogue clients and the weather). But if you only plan for the best-case scenario, you’ll likely find yourself disappointed more often than not!

I think this passage from Cup of Jo sums it up well:

“A few things will always go wrong: your flight will be delayed. Or you’ll get a bad headache. Or the weather will be rainy. Or your kids will wake up at 2 a.m. Or you’ll find a hair in your salad. And, honestly, that’s to be expected, right? Travel is still part of regular life, and tricky stuff isn’t a disaster, it’s just normal.“

Just like rain might wash out your meticulously planned beach day, in your business, a team member can just as easily get sick and it could derail your project timeline, setting you back days if not weeks! 

Wasting time dwelling on how things didn’t go your way, isn’t only counterproductive, it also drains your energy, creativity, and focus. Instead, embracing the unexpected allows you to find the silver linings, shift more strategically, and ensure that setbacks don’t overshadow your ultimate success and enjoyment.

COO Tip: Sometimes a healthy sense of humor can be a powerful tool to help you overcome the mundane and chaotic alike! Try not to take yourself or your plans too seriously. 

Don’t be Afraid to Pivot! 

This summer at the beach it POURED the entire first week! I was so bummed because I had pictured myself relaxing in my beach chair, watching the kids break in their new boogie boards. 

Getting rained out totally messed up my plans.

But we ended up having a blast, despite the bad weather. We dedicated an entire afternoon to indoor minigolf, spent way too many quarters at the arcade, and had a super fun family movie night at home!

Plus, we finally got around to visiting a restaurant I had been meaning to try forever!

Just like changing your beach plans due to inclement weather can lead you to stumble upon a hidden gem or embark on an impromptu adventure, being open to pivoting in your business will often allow you to uncover exciting, unexpected opportunities. 

I highly encourage you to channel your inner Ross Geller (“pivot!!!”). 

Remember, some of the most remarkable experiences and breakthroughs come from embracing change and being brave enough to pursue those uncharted waters. 

So, don’t be afraid to pivot, explore new avenues, and seize the possibilities that lie beyond your initial plans.

#3 Enjoy the Journey & The Destination

Do you believe the joy is in the journey, or only in the destination?

While a lot of people enjoy the vacation part of going to the beach most, there are a lot of people who surprisingly enjoy planning the trip itself more than actually traveling (it’s a real thing called vacation anticipation – look it up)!

Both entrepreneurship and a beach trip are all about finding a balance and enjoying the experience in its entirety, from start to finish, even through the not-so-fun parts!

Here’s how!

Let Yourself Dream

The process of enjoying both the journey AND the destination is all about allowing yourself to dream. When you let your imagination and creativity run wild, anything is possible. In business, this kind of dreaming is called Vision Setting. This isn’t the time to nail down all the specifics. Instead, it’s about thinking big!

Then, when you are ready to iron out the details, your excitement about the destination can fuel you (business and trip-wise). With that clear vision in mind,  you’re a heck of a lot more likely to take the steps to get there and do so with JOY and excitement!

COO Tip: Maybe it’s the artist in me, but I love making vision boards! You can use them to dream up your next tropical destination or the next chapter of your creative business! Click here to learn how to get started.

Find or Create The Joy

While slathering wriggly kids in sunscreen and schlepping 100 lbs of beach gear across the dunes might NOT be the most enjoyable thing…try and find joy in both the journey and the destination.

In business, you can channel this same energy while ALSO enjoying the fruits of your labor!

Sure, balancing your books, marketing yourself, and filing taxes may not be as fun as the creative work you do, but with the right perspective, you can find the positives even in the tasks that don’t initially spark joy. 

For example, one of my clients HATED spreadsheets but saw the need for them in her business as a graphic designer. So, she decided to have fun with it! She made them her own with fun colors, unique fonts, and lots of space (instead of tiny cells) so that she would be more inclined to use these tools regularly in her business. 

Be willing to get uncomfortable

Along the way, things can get messy. Whether it’s setting out on a beach trip or building your business from scratch, the reality is these experiences aren’t always as glamorous as they seem in Travel + Leisure magazine or Forbes. It’s important to acknowledge that both journeys come with their fair share of challenges and unexpected twists.

But at the end of the day, I truly believe that those long car rides and sandy feet make the beach views and sea breezes that much sweeter. 

In the same vein, late nights spent pouring your heart and soul into a project make the final outcome something you can genuinely be proud of. The journey may have its ups and downs, but it’s these challenging moments that make the destination all the more rewarding.

Charting The Course Toward Your Destination

This summer, whether on your way to the beach or building the creative business of your dreams, I hope you’re able to… 

  • create a plan that supports the vision you have in mind
  • go with the flow and expect the unexpected
  • savor the good, the uncomfortable, and everything in between

If you find yourself needing guidance or support to overcome your biggest challenges this summer and get back on track toward your business vision, I invite you to schedule a 90-minute Clarity Call. Together, we can dive deep into your goals and strategize practical solutions, so you’ll have more time to dip your toes in the water and enjoy the journey.


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