Navigating The Most Common Challenges When Starting a Side-Hustle or a Project

Starting a side-hustle, launching a project, or pursuing a new career interest outside your comfort zone can be extremely intimidating!  In fact, the farther away it gets from your career or personal experience, the more difficult it can seem to succeed or even be happy doing it.

Here are 7 problems most people encounter on the journey to pursuing new interests and career pathways.

1. Not knowing yourself well enough to boldly pick a new path and go; wondering if you’ll really like it or not.
2. Struggle to imagine what winning in your new field of interest could look like for you; wondering what is realistically possible given you are new to this.
3. Lacking a network in the new field; most of your network is focused on what you do currently which is what you want to move away from.
4. Financial pressure to stay at your current salary level.
5. You don’t have the necessary skills to succeed in the new field; most of your skills are focused on your current career.
6. There is no social proof that you can do the work you want; no past clients, no testimonials.
7. Last and probably the worst problem – imposter syndrome; why would anyone take you seriously in a field where you have little to no experience?

On the other hand, passion projects and side-hustles are the most effective way to approach and create new and life-changing opportunities in your life – especially the scary ones!

Empower Yourself by Picking Your Desired Projects and Side-Hustles

We are often dealt the situations or circumstances that we must pursue.  Managers tell us what the most important projects are and sometimes even tell us how to do the work.  When you apply to schools and jobs, they pick you.  If you aren’t dealt the school you wanted, you simply take what you get and run with it.  To some extent, this is the nature of some things in life.  However, it doesn’t have to be the case for everything. 

You can’t help but smile when you do something you intrinsically enjoy.  The activities that interest and stretch us create the conditions for flow, where we don’t even notice the time passing! 

When it comes to your passion projects or side-hustles, you do the picking!  Select the projects or side-hustles that are aligned with your values, passions, and purpose.  When you achieve that alignment, even if only for 6-10 hours per week, you have a reliable vehicle for tapping into your best self.

For many years, tutoring math was my side-hustle of choice because it brought me a level of joy and fulfillment that could make the worst of days, great!  In essence, my projects have always served as an effective way to unleash my best self.

Projects CREATE Balance in Your Life

Recently, I interviewed a triple board-certified physician (busy to say the least) who took on the project of writing a book.  When I asked her how she balanced the two things, her response was, “It wasn’t about balancing the two things, the book project CREATED the balance I needed in my life.”

If you’re considering launching your own project or side-hustle, you’re likely wondering whether the benefits will outweigh the challenges. Let me assure you, taking the leap and starting something on your own can be one of the most rewarding experiences of your life. Not only can it lead to financial gain, but it can also boost your confidence, help you build new skills, and create a sense of purpose and fulfillment in your life.

Here are 10 game-changing benefits to launching your own passion project or side-hustle that you won’t want to miss out on!

You Can Use Side-Hustles and Projects for Self-discovery (i.e. values, passion, and purpose)

Young people spend over $250K on university tuition to begin the process of getting to know themselves better.  Some of the same young people take a year off before or after university to backpack around some exotic part of the world for the same reason.  Working professionals are often too busy to dedicate that much time and opt for additional training or coaching.  Others pursue this in retirement.  Most spend their entire lives in pursuit of getting to know themselves.

Needless to say, this is one of the great challenges most people will pursue in their lifetime! 

Fortunately, passion projects and side-hustles have a way of helping us get closer to discovering who we really are deep down by exposing us to diverse experiences, people, places, and opportunities.  You will get to know parts of yourself that would not have otherwise been called into action.

Side-Hustles and Passion Projects Create Future Possibilities and Pathways

Engaging with projects helps you explore potential new interests and in some cases, interests that you might return to later in life.  When I launched my first project in tutoring math, I completed it and didn’t do it again until about a half year later.  Other projects had to sit on a shelf until years later when the timing was right.  Since I had already engaged in that project, I was not a stranger to it and when it was time to reactivate it, I felt sufficiently ready to move forward.

Similarly, projects also put you on a path to discovering what is possible in a new field.  When I started tutoring math, I had never considered that I might work for a learning center, launch a math coaching business, consult for a school district, teach high school and middle school math, or speak at a math conference. 

When you begin to work on a project, you begin to discover a path that you never could have imagined if you didn’t start. 

Leverage Projects and Side-Hustles to Connect with a New Community or Build Your Own

Projects give you the perfect excuse to begin attending events in your new field of interest.  Since you are working on something in that field, you now have something to talk about and more importantly, you become a contributor to the new community.  By contributing, you build stronger connections with the people in your new community. 

To learn more about entrepreneurship and tech startups, I got involved in the Techstars Startup Weekend community.  This community is global and thanks to my involvement over the years, I have connected with thousands of people around the world who have helped me reinvent my life multiple times!

In some cases, depending on your interest or project, you might have to launch a community where one didn’t exist.  Either way, you tap into a whole new world of people.

Side-Hustle Your Way to Financial Growth

If you choose to engage in a side-hustle for your project, then one of the perks you will enjoy is additional income.  Imagine not having to beg the leaders at your day job for a measly few percent raise.  Instead, anytime you want a raise you can go find a new side-hustle client or opportunity. With side-hustles, you have the power to set your own rates and decide how much extra money you want to earn. Plus, the skills and experience you gain from your side-hustle can open up new doors for career advancement and financial growth. Some side-hustle ideas or best ways to make money on the side that you can consider looking into include: freelance work, part time jobs, projects that generate passive income, online businesses or entrepreneurship, just to name a few. 

On my journey, I have been able to give myself multiple raises from various side hustles.

Cultivating Meaningful Connections for Your Side-Hustles and Projects: The Role of Networking and Mentorship

How many times have you asked someone to coffee for an informational interview or to “pick their brain?”  Maybe you called a mentor for some advice.

Imagine having a clearly defined and exciting project and asking someone in your network to help you?  This is no basic coffee chat, this is a meeting with a very specific and exciting agenda and request for support.  These are the type of asks that make people excited to want to support and work with you!  Projects will help you get the absolute maximum value from your network. 

If you don’t yet have a network or connections, consider using LinkedIn to reach out to people you admire. Send a thoughtful message expressing your interest in their work and explain how you think they could offer valuable insights or guidance for your side-hustle or project. Remember to be respectful of their time and keep your message concise and specific about your ask. It’s surprising how receptive people can be, especially if they see that you are passionate and motivated about your project.

Embracing a Purpose-Driven Life Through Side-Hustles and Projects

Sometimes what was once a dream job doesn’t feel so dreamy anymore.  The company’s mission or values may have shifted since you got there and you no longer feel you are doing meaningful or purposeful work. 

Projects and side-hustles are a great way to inject meaning and purpose back into your life.  Since you get to pick the work you do, you can pick or design a project that is both meaningful and purposeful to you.  

A few examples of what my past clients and people I’ve interviewed have shared include: marketplaces for quality childcare; life coaching; traveling and writing; NGO work; semi-professional photography; etc.

Side-Projects Help You Develop New Skills and Experience

Working professionals spend anywhere from tens to hundreds of thousands of dollars going back to school for certificates, master’s degrees, PhDs in pursuit of new skills and experience.  The problem with going back to school is that most of the experience is at best academic, theoretical, or textbook.

Projects offer you an effective way of obtaining real-world practical experience in a new field.  Just imagine how much you would learn about entrepreneurship by working on a startup project for a team of experienced founders?  Or by launching a minimum viable product of your own that earns some side-income?

Take Advantage of the Results, Social Proof, and Testimonials That Side-Hustles and Projects Offer You

When entering a new field, one of the biggest hurdles is building a reputation quickly so that you can qualify for exciting opportunities.  However, given you have little-to-no experience, it’s hard to build a portfolio of results that speak for your potential.  Projects to the rescue!

Projects are a powerful opportunity to start earning results (however small they might be at first) and accumulating social proof and testimonials from real people in the new industry that can speak for your work and future potential in your new field of interest.

When I was laid off during the pandemic in 2020, I launched a project to help nearly 1,000 other people laid off with me to prepare for their next chapter.  The work I did there helped me achieve results and walk away with powerful testimonials. 

Crush Imposter Syndrome with Side-Projects

New projects and interests can be exciting but can also feel intimidating when it’s new to you.

Testing out a small project can help you explore your new interest without over committing.

Projects also help you build confidence through small wins.  The confidence you build over time from accumulating small wins will help you overcome imposter syndrome.  If you are doing the work and it’s visible to others, then you cannot be an imposter, by definition!

Starting a project can be a daunting task, but with the right mindset and approach, it can also be an incredibly rewarding experience. If you’re thinking about starting a project, I encourage you to take that first step and reach out for help. Whether it’s through collaboration with others or seeking out mentorship and guidance, there are plenty of resources available to support your journey. Don’t let fear or uncertainty hold you back from pursuing your passion and making a difference in the world.