Are You Ready for Entrepreneurship? 5 Challenges New Entrepreneurs Face (and How to Overcome Them)

If you’re about to or have recently launched a business, you’ve probably asked yourself some of these questions:

  • Am I ready for this?

  • Am I doing it right?

  • Who do I ask for help?

  • Why does everyone else seem to know what they’re doing?

  • Will my business make money?

  • What if I fail?

Fear not, friend—these questions are a completely normal part of the entrepreneurial journey. There’s no secret club that keeps all the answers hidden in a private vault (not that we know of, anyway).

To help guide you as you build your business, we’ve put together a free Business Launch Checklist that includes 25 things to do before launching.

This article explores five challenges all entrepreneurs face and offers updated insights and resources to help you navigate them.

Get Comfortable Being Uncomfortable

We live in a world where answers are at our fingertips. Need something? Google it. Add to cart. Done. Entrepreneurship doesn’t work that way. Comparing where you are now to someone ten years into their journey can stop you in your tracks. Every successful entrepreneur started where you are now.

Sarah Blakely, founder of Spanx, famously said, “So many people don’t take risks for fear of failure. Once you redefine that, and realize that failure is just not trying, then life will open up for you in so many ways.”

If your journey doesn’t include a few failures, you’re likely playing it too safe. Expect a few "oops" moments—they’ll be learning opportunities.

Challenge 1: Financial Pressure

Financial stress is a reality for many entrepreneurs. Here’s how to minimize it:

  • Plan Before Quitting Your Job: While diving in full-time sounds romantic, having a steady income while launching your business can reduce stress.

  • Use Financial Tools: Apps like Wave or QuickBooks can help you manage cash flow.

  • Consider Funding Options: Explore government grants or crowdfunding platforms like Kickstarter for extra support.

Challenge 2: Risk Aversion

Entrepreneurship requires a certain level of risk tolerance. If you’re not ready today, that’s okay. Start small by:

  • Testing your idea with a minimal viable product (MVP).

  • Setting realistic goals and gradually increasing your risk tolerance.

  • Seeking advice from mentors or business networks like Startup Canada.

Challenge 3: Number Crunching

Many entrepreneurs dread financial management, but it’s essential.

  • Start Small: Use budgeting apps like Monarch Money to track personal and business finances.

  • Hire Help: A bookkeeper or accountant can save you time and headaches.

  • Automate: Platforms like Dext can streamline expense tracking and invoicing.

Challenge 4: Writing a Business Plan

A business plan isn’t just for funding—it’s a roadmap for success.

  • Use Templates: Tools like the BDC Business Plan Template or HubSpot's can simplify the process.

  • Focus on Key Elements: Include your mission, goals, target market, competitive analysis, and financial projections.

  • Get Feedback: Share your draft with trusted advisors for insights.

Challenge 5: Facing the Unknowns

The unknown is inevitable in business, but here’s how to prepare:

  • Validate Your Idea: Use Google Forms for surveys or pre-sales on Shopify.

  • Build a Network: Join LinkedIn groups or attend events by platforms like Eventbrite.

  • Invest in AI Tools: Leverage tools like ChatGPT or Jasper to improve efficiency.

New Considerations for Today’s Entrepreneurs

  • Sustainability Matters: Incorporate eco-friendly practices, like using recycled packaging or digital business cards.

  • Mental Health is Key: Apps like Calm or Headspace can help you manage stress.

  • Diversity Drives Success: Explore grants and mentorship programs for underrepresented groups, such as the Women Entrepreneurship Strategy.

Final Thoughts

Sarah Blakely’s advice is timeless: The only failure is not trying.

If you’re passionate about your business idea, confident in its potential, and ready to learn from failure, you’re on the right track.

Remember, the entrepreneurial journey is a marathon, not a sprint. Take it one step at a time, stay open to learning, and trust that growth comes through perseverance.

Sarah Gencarelli

Sarah Gencarelli is a creative strategist and co-founder of Wild Idea Co., with over a decade of experience helping businesses craft compelling brand strategies. Passionate about storytelling and connecting brands with their audiences, Sarah blends creativity and practicality to deliver impactful results. She thrives on helping Canadian entrepreneurs bring bold ideas to life and create brands that feel authentic and memorable. When she’s not brainstorming the next big idea, Sarah enjoys spending time with her family and finding inspiration in the world around her.

https://www.sarahgencarelli.com
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