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Beyond the 9-to-5: The Rise of the Modern Entrepreneur

Updated: Jun 5

If you’re like me, you’ve spent enough time scrolling through instagram to be equally inspired and down right floored by the stardom that some have found through the simplest streamlined enterprises. 

woman pinning photos to corkboard

The woman who left her job during the 2020 madness and is now making 6 figures from her garage workshop...
The best friends whose slick scheme won favor on Shark Tank and now have built brands that are common household names...
The “silly” gadgets and gizmos that someone famous recommended and now a backyard business has gone viral and she’s pumping out her products worldwide...

The lists are endless and this “land of the free and home of the brave” truly does offer the iconic opportunity to “live the American dream” to those bold enough to embrace entrepreneurship and step out of the status quo.

But for every store that skyrockets are a dozen business that go bust. What are the key factors to launch strong and keep your business in the black? Grab a pen and paper and read on girlfriend….take notes!  We have a lot to cover!

With the hundreds of websites I’ve designed over the years for boss babes, aspiring creators and established entrepreneurs, I’ve noted a few trending indicators that point to success:

Do Your Research

Good questions to ask before you convert that spare bedroom into your new aesthetic office are these:

  • What problem am I solving? Identify a clear problem to be certain that there is a demand for your service or product.

  • Who is my target audience? Knowing who you are marketing to will help you dial in your overall approach.

  • Is the market already saturated? See who else is catering to your niche market already and if there is demand for what you’re offering.

  • What is the competition? Who is crushing it? What are they doing? Watch and learn!

Example: Airbnb

  • Problem Solved: Founders Brian Chesky and Joe Gebbia identified a need for affordable and unique lodging options for travelers.

  • Research: They discovered that during major events, hotels were often fully booked, creating an opportunity for a new kind of lodging service. They also studied existing platforms to understand their shortcomings.

  • Outcome: Airbnb transformed from a side project into a global hospitality giant.

It Takes Money To Make Money

Before you sell a kidney or pawn your grandmothers antique wedding ring to front the money for your new business, take an objective view at what it’s going to take to fund a start up or side hustle. (psst...did you know I have my own side hustle called "Harken" where I promote vintage farmhouse home decor? Check it out here.)

Cost analysis is an easy one to undervalue in the passionate pursuit of starting your own business.  In addition to raw materials, factor in expenses like any help you may need (with your business or with childcare or household responsibilities to free you to you focus on business).

Consider the cost of any specific licensing or business permits you may need to operate.

  • Do you need business insurance?

  • What will you be taxed as a self-employed? 

  • What are the overall operational costs?

Professional fees like legal advice, accounting and consulting can add up quickly. Remember that Rome wasn’t built in a day and it wasn’t cheap. Budget wisely and invest in the right tools and resources that will give you the most bang for your buck.

Example: Warby Parker

  • Initial Costs: The founders, while in business school, pooled together their savings to create their first line of affordable, stylish eyewear.

  • Cost Analysis: They meticulously calculated manufacturing costs, shipping, and potential operational expenses.

  • Outcome: Warby Parker is now a leading eyewear brand, demonstrating the importance of sound financial planning.


"Starting a business on the side while you still have a full-time job is one of the best ways to make your entrepreneurial dreams come true."

- Angie Hicks (Co-founder of Angie's List)


female entrepreneur working

Fail To Plan, Plan To Fail

Defining your goals and outlining what you want to achieve will help you stay on track and not get bogged down in the minutia.  Take a personal retreat weekend to devote uninterrupted time to mapping out a plan. Or at the very least, block off an afternoon at a coffee shop with a skinny latte in hand.  Draft your ideas. Create a mood board. Outline a 3 month, 6 month, 1 year plan.  These things can be changed as you evolve as a company so flexibility is key.  But the exercise of converting all your daydreams and brainstorms into Word documents, Pinterest Boards and spreadsheets will provide a strong leg to stand on as you begin the process of implementation.

Example: Glossier

  • Goal Setting: Emily Weiss, the founder, started with a beauty blog called "Into The Gloss" to build a community and understand her audience.

  • Strategic Planning: She used feedback from her readers to create a line of beauty products tailored to their needs.

  • Outcome: Glossier grew rapidly due to its clear goals and strategic planning, becoming a highly influential beauty brand.

Stand Out, Don’t Fit In

Unlike middle school, in the sphere of entrepreneurial-ship, this is your chance to shine and really leverage your unique skill set, engaging personality and one-of-a-kind ideas.

What makes you unique and sets you apart? Steal the spotlight by being human and relatable. How does one stand out?

  • Live authentically: share your compelling brand story that will resonate with your audience

  • Emotional connection is an invaluable tool: go above and beyond making every effort to connect with customers through timely responses and over the top customer service.

  • Person > Product: if someone loves you, they’re going to love your product or service. Focus more on making those personal connections rather than pushing a product.

  • Transparency and Trust are foundational to any business. The truth of the matter is, you’re going to drop the ball occasionally or mistakenly mix up an order. Taking a posture of humility and graciously fixing the problem will win you a returning customer!

Example: Spanx

  • Uniqueness: Sara Blakely created Spanx to solve a personal problem with undergarments, leading to the creation of a whole new product category.

  • Authentic Story: She leveraged her personal story and relatability to connect with customers.

  • Outcome: Spanx became a billion-dollar company, setting itself apart in the competitive fashion industry.

Protect Your “Why” 

When it stops being “fun”, you’ve got to take a step back and reassess. Running a side hustle is 100x harder (and also a million times more rewarding) than working for someone else and just collecting a paycheck. When you start a business, you’re pouring your heart and time and resources (and blood, sweat and tears) into something you love. Your business will only be as healthy as you are.  From the get-go, establish routines, boundaries and patterns that protect your family, your sanity and your bank account.  Its always wise to have a spouse or close friend as a sounding board to help remind you of your “why” when the going-gets-tough! 

Example: Toms Shoes

  • Core Mission: Blake Mycoskie founded Toms with the mission of giving back—donating a pair of shoes for every pair sold.

  • Maintaining Purpose: Despite the company's growth, it remained committed to its social mission.

  • Outcome: Toms not only succeeded commercially but also created a powerful brand ethos that attracted a loyal customer base.

Whether you’re a multitasking mom or a nine-to-five boss babe, there is innumerable untapped potential for you to convert those great ideas of yours into a lucrative enterprise and I’ll be your biggest cheerleader!  Dust off those ideas you’ve been mulling over in the break room at work and finally take a chance on your dreams.  Just make sure you’ve done your homework so you can totally crush your new endeavor with style and sass!  That imaginary side hustle just might become the next big thing.  I’ll be watching and waiting for you to go viral!

beautiful feminine desktop


Are You Ready to Start Your Side Hustle?

Take the Quiz!

(scroll down for the quiz results)


1. Have you identified a clear problem that your product or service will solve?

A) Yes, I have a well-defined problem and solution.

B) Sort of, I have an idea but it's not fully developed.

C) Not yet, I'm still brainstorming.

2. Do you know who your target audience is?

A) Yes, I have a specific audience in mind.

B) I have a general idea but need to refine it.

C) No, I haven't thought about it.

3. Have you researched the market to understand the competition?

A) Yes, I know who my competitors are and what they offer.

B) I have some knowledge but need more information.

C) No, I haven't looked into it yet.

4. Do you have a budget plan for your startup costs and ongoing expenses?

A) Yes, I have a detailed budget plan.

B) I have a rough estimate but need to finalize it.

C) No, I haven't considered the costs.

5. Have you set clear, achievable goals for your business?

A) Yes, I have short-term and long-term goals.

B) I have some goals but they are not well-defined.

C) No, I haven't set any goals yet.

6. Are you prepared to handle the emotional and physical demands of starting a business?

A) Yes, I have a support system and coping strategies in place.

B) I'm aware of the demands but not fully prepared.

C) No, I haven't thought about this aspect.

7. Do you have a plan to differentiate your business from the competition?

A) Yes, I have a unique value proposition and strategy.

B) I have some ideas but need to develop them further.

C) No, I haven't figured this out yet.

8. Are you committed to maintaining a healthy work-life balance?

A) Yes, I have set boundaries and routines.

B) I know it's important but haven't implemented it yet.

C) No, I haven't considered this aspect.


Quiz Results:

Mostly A's: Entrepreneur Extraordinaire

You're well-prepared to start your side hustle! You have a clear plan, understand your market, and are ready to tackle the challenges ahead. Keep up the great work!

Mostly B's: Aspiring Entrepreneur

You have a good foundation but need to refine some areas. Take the time to develop a clear plan, research your market thoroughly, and set achievable goals. You're on the right track!

Mostly C's: Budding Dreamer

You have the enthusiasm but need to do more groundwork. Focus on identifying a clear problem to solve, understanding your target audience, and creating a detailed plan. With some preparation, you'll be ready to launch your side hustle!

girl boss holding papers

Need Expert Advice And/Or Web Design Services?

You've got the passion and the ideas—now let’s bring them to life! Whether you need guidance on launching your business or a stunning website to showcase your brand, I’m your girl and I'm here to help. Together we'll create something amazing! Reach out today to get started on your journey to success. I'll be cheering for you.


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