5 Psychological Barriers to Starting a Side Hustle (and How to Overcome Them)

For the past seven years I have faced significant psychological barriers when trying to side hustle. I’ve watched so many people smash their goals and I just remained stagnant, watching my confidence dissipate.

One thing that I most definitely know is that starting a side hustle is an excellent way to increase your income and explore your interests. However, many people (such as yours truly) face mental obstacles that prevent them from taking the first step. Understanding and overcoming these psychological barriers is crucial for turning your idea into reality. Here are five common challenges and practical solutions to help you move forward:

Fear of Failure

Fear of failure is most certainly something that has held me back, and I assume if you are reading this, is something that is likely to be holding you back too.

What Is It?

Fear of failure is one of the most common reasons people hesitate to start a side hustle. It’s completely normal to worry about losing money, facing criticism, or not meeting your expectations. For some, it’s the fear of wasting their time (like me) and resources. For others, it’s the thought of public embarrassment if things don’t go as planned. These concerns can feel overwhelming and may lead to procrastination or even giving up before you begin.

But here’s the truth - failure is a great way to grow. Every successful side hustler or entrepreneur has experienced many setbacks along the way. Rather than seeing failure as a reflection of your abilities, think of it as a stepping stone - a chance to learn, improve, and move forward.

How to Overcome It

• Reframe Failure
  Instead of viewing failure as a sign to quit, try to see it as constructive criticism. If something doesn’t work, it’s not the end - it’s an opportunity to understand what you need to adjust. For example, if a product doesn’t sell well, it doesn’t mean you’ve failed. It might just mean you need to target a different audience, change your prices, or try a new approach. Shifting to a growth mindset can make the idea of taking risks feel much less daunting.

• Start Small
  Taking small steps is a great way to ease into your side hustle while minimising risks. If you’re considering selling handmade crafts, start with a small batch and test it with a few friends or at a local market. Thinking about freelance work? Begin with a single project to see how it feels. Starting small allows you to experiment and build confidence without feeling overwhelmed. It’s much easier to adjust your plans when the stakes are lower.

• Celebrate Your Wins
  It’s important to recognise and celebrate the little victories along the way. Did you create a plan for your side hustle? That’s progress! Did you secure your first customer? That’s a big win! By focusing on these smaller achievements, you’ll create momentum and remind yourself that you’re moving forward. Success is built step by step, so every accomplishment really does matter.

Fear of failure is a natural part of stepping into the unknown, but it doesn’t have to hold you back. By shifting your perspective, starting small, and appreciating your progress, you can turn that fear into a motivator for growth. You’ve got what it takes to make this work - so take that first step with confidence.

Imposter Syndrome

If you’ve ever felt like you’re not good enough to start a side hustle or that you’re somehow “faking it,” you’re not alone. This feeling, known as imposter syndrome, is something that many of us experience, especially when trying something new. It can make you feel like you don’t truly deserve your success, even though you have the skills and experience to make your side hustle work.

Imposter syndrome often shows up when we compare ourselves to others. You might look at someone else’s business and think ‘why would anyone be interested in what I have to offer?’ It’s completely natural to have these doubts, but it’s important to remember that everyone, even the most successful entrepreneurs, has felt this way at some point.

So, how do you get past these feelings and build confidence to continue with your side hustle?

• Acknowledge Your Strengths
  The first step to overcoming imposter syndrome is recognising what makes you unique and capable. Take a moment to reflect on your strengths, skills, and past achievements. This could be anything from qualifications you’ve earned, projects you’ve successfully completed, or skills you’ve developed over time. It’s important to remind yourself that you bring something valuable to the table. Whether it’s your creativity, problem solving abilities or expertise in a particular area, acknowledging your strengths can help boost your confidence. Seeing your accomplishments in black and white can make it much harder to dismiss your abilities. Conversely, you do not need to be an expert on a given topic. You just need to know more than someone else.

• Seek Constructive Feedback
  Sometimes, all it takes is a little reassurance from others to remind you of your worth. Reach out to trusted friends, mentors, or colleagues and ask for constructive feedback. People who know you well can often see your talents more clearly than you can and their positive feedback can help you realise how much you’ve already achieved. Constructive feedback is also useful for identifying areas where you might need improvement, giving you the opportunity to grow and build even more confidence.

• Take Action
  One of the most powerful ways to quiet the voice of imposter syndrome is to take action - no matter how imperfect it feels. The truth is, no one starts out perfect, and there’s no such thing as being 100% “ready” to launch your side hustle. The more you delay starting, the more self-doubt can creep in. Trust me, I know.

  The best thing you can do is just begin. If you’re launching a new product or service, start small or offer a limited number of slots to test the waters. You don’t need everything to be perfect right away. Mistakes and setbacks will happen and that’s absolutely fine. What matters is that you’re learning as you go and making progress. Taking action helps you realise that you’re capable of more than you think.

Analysis Paralysis

Overthinking is something we’ve all been guilty of, especially when starting a new side hustle. It’s the tendency to get caught in a cycle of endlessly researching, planning, and analysing every possible outcome without actually taking any concrete steps towards your goals. You might find yourself stuck in a cycle of ‘what if’s’ and ‘buts’, leading to procrastination and frustration. Instead of moving forward, you become stuck which only makes it harder to get started.

If you’ve ever felt overwhelmed by the amount of information you need to process before launching your side hustle, you’re not alone. While it’s important to plan and research, overthinking can prevent you from making progress. But the good news is, there are simple ways to break the cycle and start taking action.

What Is Overthinking?

Overthinking occurs when you spend excessive time and energy thinking about a task or decision, often to the point where it hinders progress. It’s easy to get stuck in the details, second-guessing every choice and trying to account for every possible outcome. While research and careful consideration are important, overthinking can leave you paralysed by indecision, preventing you from taking the first steps.

When overthinking takes over, you might find yourself trapped in a never-ending cycle of planning and researching, but you don’t make any real progress. This can be especially frustrating when you're trying to launch something new, like a side hustle, where action is essential for success.

How to Overcome Overthinking

• Set Deadlines for Research and Decision Making
  One of the best ways to avoid getting stuck in overthinking is to set yourself some deadlines. Give yourself a specific time frame for research and decision making, whether that’s a few hours or a couple of days. Once that time is up, make your decision and move on. Deadlines create a sense of urgency that pushes you to make choices without getting bogged down in the details. For example, if you’re deciding on the branding for your side hustle, set a deadline to finalise your logo and brand colours. Once the deadline is reached, don’t allow yourself to keep tweaking. This helps you avoid perfectionism and makes it easier to take action - trust me, this is something that you need to do.

• Break It Down into Smaller Tasks
  When a goal feels overwhelming, break it down into more manageable tasks. You can then tackle one step at a time rather than trying to do everything at once. For example, if you’re starting an online shop, your goal might be to launch the store but this can feel huge and intimidating. Break it down into smaller tasks, like selecting a platform, creating your product listings and setting up payment methods. By focusing on smaller, achievable tasks, you’ll make steady progress without getting overwhelmed.

• Embrace Imperfection
  Perfectionism often feeds into overthinking. You might feel that everything has to be perfect before you launch or make a decision, but that’s simply not the case. Embrace the idea that your first attempts don’t need to be flawless. Instead of striving for perfection, treat your initial efforts as experiments. Your first product launch, marketing campaign, or website design might not be perfect, and that’s completely okay. The key is to get started, learn from the process, and improve as you go. Every mistake or challenge is an opportunity to refine your approach and grow your skills. The more you focus on action rather than perfection, the more confident you’ll become in your side hustle journey.

Fear of Judgement

Starting a side hustle is an exciting and rewarding endeavour, but for many people, there’s one major hurdle that often holds them back: the fear of what others might think. This fear can be paralysing, leading to hesitation when it comes to promoting your side hustle or even sharing it with your closest friends and family. You might worry about being judged, ridiculed or simply not being taken seriously. These concerns can prevent you from taking the necessary steps to grow your business.

It’s completely normal to feel self-conscious or insecure when you’re starting something new. But it’s important to remember that the fear of judgment doesn’t have to control you. You can overcome these feelings and promote your side hustle by focusing on your goals, building your confidence gradually, and surrounding yourself with supportive people.

What Is the Fear of Judgment?

The fear of judgment is the anxiety or concern about what others might think of your side hustle.

This fear is often rooted in the desire to be liked and accepted by others, which is a natural human instinct. However, when it comes to pursuing your passions and building something of your own, worrying about others’ opinions can hold you back. The fear of judgment may prevent you from sharing your idea, marketing your product, or even telling people you’ve started a side hustle in the first place.

How to Overcome the Fear of Judgment

• Focus on Your Goals
  When the fear of judgment creeps in, the best thing you can do is reconnect with your why. Why did you decide to start your side hustle in the first place? Was it to follow a passion? To create financial freedom? To bring an idea to life? Keeping your reasons at the forefront of your mind can help drown out the negative thoughts and remind you of what really matters.

• Begin Quietly
  If you’re feeling particularly hesitant about sharing your side hustle with the world, start small and quiet. You don’t have to go public right away. Begin by testing your ideas in a low-risk environment, like sharing them with a small group of trusted friends or family members who are supportive and encouraging. This can help you build confidence in your offering and get positive feedback before you decide to expand your audience.

• Join Supportive Communities
  One of the most powerful ways to overcome the fear of judgment is to surround yourself with like-minded people who can support and encourage you. There are countless online communities, forums, and social media groups full of people who are on a similar journey. These communities provide a safe space where you can share ideas, ask questions, and receive feedback without the fear of judgment. Being around people who share your passion and are committed to their own side hustles can also inspire you to push through your fears.

Doubts About Financial Success

When starting a side hustle, one of the biggest concerns many people face is the fear that it won’t be profitable. Whether you’re selling a product, offering a service, or launching an online business, it’s easy to feel uncertain about how to price your offerings and whether you’ll be able to make enough money to justify the time and effort you're putting in.

It’s completely normal to have concerns about whether your side hustle will be financially successful, but these worries shouldn’t hold you back.. With the right approach and mindset, you can overcome these uncertainties and build a profitable business.

What Is the Fear of Uncertainty Around Profitability and Pricing?

For many side hustlers, especially those new to business, the fear of whether your venture will be profitable can be overwhelming. Will people pay for your product or service? How do you set a price that reflects the value you're offering but still appeals to customers? These are valid questions, and the uncertainty around pricing can often lead to analysis paralysis.

In addition to pricing, you might worry about how much time and money to invest upfront. How much should you spend on marketing, inventory, or business tools? What if you spend money without getting a return? These questions can create doubts and prevent you from taking action, but with the right strategies, you can reduce this uncertainty and set yourself up for success.

How to Overcome the Fear of Uncertainty Around Pricing and Profitability

• Conduct Market Research
  One of the most effective ways to overcome the uncertainty surrounding pricing is to conduct thorough market research. Before you set your prices or launch your products, it’s important to understand the market you’re entering. Analyse competitors and similar businesses in your niche to see how they price their offerings and what kind of demand exists. Take note of competitor priceing, customer expectations and market demand.

• Start with Low Costs
  Another way to ease the financial pressure when starting a side hustle is to keep your expenses as low as possible in the beginning. Starting with low costs allows you to test your business idea and pricing strategy without the risk of overspending. For example, if you’re selling physical products, consider starting with just a few products or selling through a low-cost platform (such as Etsy or eBay) before investing in your own website or larger inventory. If you’re offering services, offer your skills to a few clients at a discounted rate or run a pilot project to gather feedback. Starting small helps you minimise financial risk while you figure out what works and what doesn’t. This way, you can gradually scale your business as you gain more confidence in your pricing and profitability. Plus, it allows you to make adjustments along the way without risking too much capital.

• Value Your Skills and Expertise
  One of the most important things to remember when pricing your side hustle is that your skills, time, and expertise are valuable. Many new entrepreneurs, especially those starting service-based side hustles, often undervalue their work because they don’t feel experienced enough or fear pricing too high. However, it’s essential to recognise that the value you provide to your clients is worth paying for. It’s important to remember that people are willing to pay for the value you offer, even if you’re just starting out. Don’t undervalue your worth because of uncertainty. Charging what you’re worth helps you build a sustainable and profitable side hustle, rather than underpricing and burning out.

As someone who has experienced all of the above and more, my final (and most important piece of advice) would be to just start and not overthink anything. My life might have looked so different if I had started and stuck to it all those years ago.