Side Checks Podcast

How I Knew It Was Time To Pivot My Side Hustle

March 27, 2023

I'm Amy! I'm a small business educator who got hooked on entrepreneurship after starting a cleaning business in college. Since my Clorox days, I've built many businesses. I've sold businesses. And I've helped small business owners do the same.


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What I Learned From Changing Directions Within My Side Hustle Career

There was a time when I thought my lengthy entrepreneur resume was a bad thing. That my multiple interests and the exploration phase of entrepreneurship were signs that my aspirations were scattered or uncertain. And this couldn’t be more wrong. In this episode, we dive into how I knew it was time to pivot my side hustle, the difference between exploration and pivoting, how to know when it’s time to pivot, and how to pivot within your career in a way that won’t leave you bumped and bruised.

The Importance of Pivoting Versus Exploring

In this episode, I point out the important difference between pivoting and exploring. This difference between these two phases of entrepreneurship is important to understand and identify, especially for side hustlers. We want to banish shame from exploring various side hustles. And also, highlight the significance of pivoting.

I define pivoting as the change within entrepreneurship that changes our main revenue stream. When we pivot inside our side hustle, we are changing how we receive income. This usually includes changing this business model itself.

When we explore various side hustles, we may find ourselves adding on services or diving into different business models back to back. It’s important that we treat career explorations as that; explorations. And that we have a solid game plan for earning income as we explore different career options.

Positive Career Exploration

In this episode, I walk you through all the various explorations of my side hustle career. From my watercolor pet coffee mug line, to my pet photography days, to my wedding photography business, and to date with my food photography business; I highlight that exploration and pivoting has been a constant for me. I think it’s important to normalize this.

Entrepreneurship is the only job you’ll ever have where you don’t get paid for learning on day one

Amy Schmidt, Side Checks Podcast

In my early days of entrepreneurship, I began to pivot my side hustle a lot. And with this came some shame. I thought that changing business models meant that I wasn’t good at business. Now, there is some truth that if your business model is ever-changing, it is harder to earn consistent income. However, entrepreneurship does require a few trail periods.

You wont understand what you need from business until you’re truly inside it. And until you explore running a type of business, you won’t be able to truly weigh the pros and cons to evaluate if you want to continue. Unfortunately, entrepreneurship is not like a summer internship.

However, there are positive career exploration paths you can take. If you are pursuing entrepreneurship, consider how you can lightly explore a career path before diving in for yourself. This may look like talking with a fellow expert, or running a trail base. One thing that helps this career exploration phase is to keep business operations simple. Tune into this episode where I talk with my former business coach about simplifying business decisions for income optimization.

My Full Time Wedding Photography Career

After exploring entrepreneurship, I was able to settle into the niche of wedding photography and build a full-time business, earning consistent income. My full time business did not happen overnight. In fact after I decided to niche into weddings, it would be about 6-8 months before I was able to earn enough income. And 1 year until my income felt truly reliable.

When starting my business, I did not walk through my business model with the lens of “what could go wrong”. But instead, I white-knuckled my way to earning the title of “full time wedding photographer” status. All of my income was dependent upon me showing up and doing well.

Towards the end of my wedding photography career, I had no plan to pivot. However, I did start seeing holes within my business plan. One being always working weekends. And the other being a future maternity leave. With wedding photography, there was no plan put in place for scheduling pregnancy with brides nor a plan for post-pregnancy.

When I Knew It Was Time To Pivot

In this episode of Side Checks, I explain that when it was time to pivot my side hustle, the pivot was forced. With the news that I was moving back home to South Carolina, my local service-based business became almost obsolete overnight.

My inbox would collect hundreds of dollars worth of inquiries each week. However, I couldn’t accept any since I had built a business completely service based from my two hands. I knew if I ever went back into entrepreneurship, it was time to pivot.

For 1-2 years, I was able to fall back on a college degree and return to a second and last corporate role. There I was able to off board my existing clientele in the Chicago area will work full time and not have to worry about entrepreneurship.

However, that didn’t last long. After my wedding photography business was completely off boarded, I then knew it was time to pivot into something with longevity. For the first time in entrepreneurship, I asked myself what I needed from business and built from there.

There’s a reason you’re looking to pivot. Instead of diving into what the reason is and focusing on what your current business isn’t giving you, I want to encourage you to focus on what you need out of entrepreneurship instead

Amy Schmidt, Side Checks Podcast

From there, I built my food photography side hustle that I still run today. With this business, I am able to earn income by utilizing my photography skill in my own home. This makes for zero travel and quicker turnover times for projects. I am also able to scale this business by hiring team members who can help increase inventory, not created by my own hands.

Pivoting Checklist

If you’re looking to pivot your side hustle, know that this is a normal part of entrepreneurship. Even for side hustlers. Running a part-time business has so many amazing perks. One being that you are able to make safer pivots into different areas of entrepreneurship, all while knowing your total income won’t be affected.

The first place you want to start when considering pivoting your side hustling is asking yourself questions to gain clarity. Pivoting business requires a lot of work. And should only be used as a last resort, even though the phase is important. However, if you can tweak your business model, rather than pivot it completely, this is much easier.

Ask yourself these questions:

  • What are my goals?
  • What are my current needs?
  • Does my side hustle satisfy both goals and needs?
  • Have my goals or needs shifted?
  • Do I see longevity in my path that I’m on?
  • Is there anything I can tweak to solve an issue?

If your goals have shifted and are not currently being met and you do not see longevity on your current path, it may be time to pivot your side hustle. As I mentioned in the episode, if you’re considering pivoting your side hustle, start by asking yourself what it is you need to pivot into. Answering this question with clarity and details will help make your next pivot, the best one yet.

Want to start making more of your time when it comes to your business? Take my free workshop Life-Proof Your Side Hustle to put a forever end to not knowing what to work on, and when.

I'm Amy Schmidt

Hi there!

I'm a small business cheerleader, strategist, and course creator who loves seeing others earn income in unconventional ways. I started a cleaning business in college and have side hustled since, selling my latest part-time business for $151,000.


I'm Amy Schmidt, your new business strategist!

I'm a small business development and sales strategist who loves seeing others earn income in unconventional ways. I started a cleaning business in college and have side hustled since, selling my latest part-time business for $151,000

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