Exploring Side Hustle Options: What’s Possible and What’s Practical
Our journey with side hustles has been both diverse and rewarding. We’ve been fortunate to have unique opportunities along the way. For example, I owned a condo in Florida before marrying Ben, which we now rent out as a long-term property. It provides steady income without much oversight, making it a great example of how existing assets can create new revenue streams. At our current home, we have the flexibility to rent two separate spaces, and we chose a mix of short-term and long-term rentals to balance consistent income with the higher earnings potential of Airbnb.
Not every side hustle has been a long-term fit. We tried pet sitting through Rover, which started strong but eventually fizzled out as other ventures took priority. Side hustles are about finding what fits your schedule and your interests over time.
In addition to property-based income, I’ve worked as an independent contractor, implementing third-party SaaS software solutions for businesses. This role allowed me to build skills that aligned with my background and interests. Now, I’m expanding even further by pursuing certification as a career and executive coach specializing in ADHD and neurodiversity. For me, this is an opportunity to turn my passion for supporting others into a flexible side business that aligns with my skill set.
Short-Term Rentals (Airbnb)
We started our Airbnb in Oct 2016 and have grown it to a 90% occupancy rate for the dates we allow people to book. We love the flexibility that affords us the ability to block days when we need a break and want some privacy. Hosting on Airbnb has been one of our most successful side hustles, but like any venture, it comes with its own set of pros and cons. Here’s a breakdown based on both industry insights and our personal experience.
Pros of Airbnb Hosting
Flexibility: One of the greatest advantages of Airbnb is the ability to control when the property is available. We've found it incredibly helpful to block off dates when we need privacy or a break from hosting. This flexibility is particularly useful if you want to keep the property available for family or friends or just to recharge.
Higher Income Potential: Compared to traditional rentals, short-term rentals like Airbnb often yield higher income, especially during peak travel seasons. In our case, having a unique property like a tiny home has also attracted a steady stream of guests, helping us maintain high occupancy rates.
Control Over Guest Interactions: Airbnb lets you set house rules, vet guests to an extent, and manage bookings directly. This level of control has allowed us to create a welcoming experience while setting clear boundaries, ultimately fostering a better guest-host relationship.
Cons of Airbnb Hosting
Challenging Guests: Hosting isn’t always easy. We've encountered guests who test boundaries or fail to respect house rules. Some guests require more communication and problem-solving, which can add stress and take time.
Potential for Unexpected Issues: From frozen pipes to blown breakers, unexpected maintenance needs can arise. Airbnb properties often require frequent attention and upkeep, especially when guests are constantly coming and going, which can add stress.
Judgment from Neighbors: Not all neighbors appreciate the increased traffic and temporary visitors that come with hosting. This aspect can be tricky to navigate, as the judgment or concerns from neighbors may influence how often you rent out the property.
Key Takeaway
Airbnb hosting offers significant earning potential and flexibility, but it requires consistent effort and attention. If you’re comfortable handling guest interactions, property upkeep, and the occasional neighborly tension, short-term rentals can be a rewarding way to generate extra income.
Long-Term Rentals
In addition to our short-term rental, we’ve also had success with long-term rentals. We’re fortunate to have both a condo I owned before meeting Ben and a separate cabin on our property that we rent out. Long-term rentals have been a steady source of income, with a different set of pros and cons compared to short-term hosting.
Pros of Long-Term Rentals
Consistent Monthly Income: One of the biggest advantages of long-term rentals is the predictable income. Unlike the seasonal ups and downs of short-term hosting, having long-term tenants provides a steady cash flow each month, which helps with budgeting and financial planning.
Lower Turnover: With long-term leases, we avoid the constant cycle of new guests and all the cleaning, coordination, and preparation that comes with it. This reduces the overall workload and makes managing the property simpler.
Reduced Management Needs: Since tenants stay for extended periods, there’s less day-to-day involvement. Maintenance and repairs are less frequent, and once tenants are settled, the management demands decrease significantly.
Cons of Long-Term Rentals
Tenant Management: While long-term rentals require less frequent interactions, tenant relationships are more important. Managing tenant expectations, addressing concerns, and ensuring clear communication are essential for maintaining a positive, trouble-free experience.
Potential for Property Wear and Tear: With long-term tenants, wear and tear are inevitable. Over time, regular use can lead to maintenance needs that must be managed to keep the property in good condition, often requiring a higher initial investment in durable furnishings and fixtures.
Longer Commitment: Unlike short-term rentals where you can adjust availability quickly, long-term leases mean committing to a tenant for several months or even years. This limits flexibility, especially if you might want to use the property for other purposes in the future.
Key Takeaway
Long-term rentals provide stability and consistent income with less day-to-day management but require patience and a strong commitment to building positive tenant relationships. For those who prefer a hands-off approach and steady earnings, long-term rentals can be a solid option.
Consulting
Beyond rentals, consulting has been another fulfilling and flexible side hustle for me. I’ve had the opportunity to leverage my skills in leading cross-functional teams and implementing third-party SaaS software solutions for clients. Now, with Shimko Consulting, LLC, I’m able to market these skills and expand my business, offering services through my website. Consulting allows me to take on projects that align with my expertise while building a business that reflects my values and strengths.
Pros of Consulting
Setting My Own Hours: One of the biggest advantages of consulting is the ability to work on my own schedule. I can structure my time in a way that balances my other commitments, making it an ideal choice for someone with diverse interests and responsibilities.
Choosing My Clients and Projects: Consulting allows me to select projects that align with my skills and passions. This freedom to pick clients lets me focus on work that’s meaningful and fulfilling, rather than taking on projects out of necessity.
Potential for Growth and Branding: Building Shimko Consulting, LLC gives me the opportunity to establish my own brand. Marketing my services on my website allows me to reach a broader audience and further develop my expertise and reputation.
Cons of Consulting
Business Ownership Stress: Running your own consulting business comes with responsibilities and challenges that go beyond the consulting work itself. There’s a lot of behind-the-scenes work, from handling finances and contracts to managing marketing and client communications, which can add stress.
Finding Clients: Securing a steady stream of clients can be challenging, especially when starting out. Marketing, networking, and consistently showcasing my skills are essential to attracting clients, but this requires ongoing effort and time.
Key Takeaway
Consulting offers freedom and the potential to shape my own business, but it also requires resilience, patience, and the willingness to manage various aspects of business ownership. For those who are ready to market their skills and take on the responsibility, consulting can be a rewarding and empowering side hustle.
Comparing Your Options: Finding the Right Fit
Choosing the right side hustle depends on what fits your lifestyle and personal goals. Each option has its own demands, so it’s essential to reflect on what you’re comfortable with. Here are a few questions to help you decide:
How much time do you have to invest? Some side hustles, like Airbnb, require frequent attention, while others, like long-term rentals, are more hands-off.
How much stress are you willing to take on? Every venture has challenges, so think about how much additional stress you can manage.
What are your passions and strengths? Finding a side hustle that aligns with your interests—like consulting if you enjoy project-based work or coaching if you love helping others—can keep you motivated.
Is there a path here toward your bigger goals? For me, coaching and consulting offer ways to connect with others, helping me step into my role as a “crown-straightener” and cheerleader.
The right fit for a side hustle isn’t always obvious, so it helps to try different things, adjust based on what works, and keep an open mind.
Conclusion: Building a Side Hustle Portfolio
Creating a side hustle portfolio that aligns with your goals and lifestyle is a rewarding journey. The beauty of side hustles is that they let you explore new interests, test out career possibilities, and find ways to achieve financial freedom. Don’t be afraid to experiment, make mistakes, and learn as you go. Be curious, talk to people, take classes, and explore opportunities.
Ultimately, there’s no one-size-fits-all solution, but starting small and testing different options can help reveal what works best for you. Whether it’s a side hustle for extra income or a path toward a career change, each step you take will bring you closer to the life you envision.
