How to prepare for entrepreneurship

When you start your own business every aspect of your life has the potential to shift and expand, and as a soon-to-be entrepreneur, you get to decide exactly how you want to build your business while living your most meaningful life. 

As you begin your career transition, it’s important to understand that entrepreneurship is both a practice and a process. Your transformation doesn’t have to happen all at once, and it’s essential to define success on your own terms and ensure you’re well-supported as you move forward.

Instead of getting overwhelmed by the thought of taking the leap, allow the guidance below to help you expand your mindset and prepare to take meaningful action toward your dream. 

1. Make yourself part of your business plan

If you’re considering entrepreneurship, chances are you’ve heard many people talk about the hustle and grind required to build a business. While this approach may generate faster results in the short term, it often leads new entrepreneurs to build companies at the expense of themselves, forgetting their own needs, well-being, and values in the process.

Contrary to popular rhetoric, entrepreneurship has the potential to be a supportive and inspiring experience if you choose to approach it that way. When you're clear on who you are and what you need, your business can become a powerful extension of your values and personal convictions.

Before you do anything else, make sure you clarify your needs as an entrepreneur and identify specific values and boundaries you want to incorporate into your business:

  • What do I need my business to give me? Paint the most ideal picture. (E.g., a minimum amount of time off during the year, a specific amount of income per month, clients that you love working with, a flexible schedule, etc).

  • What are my values and how will I incorporate them into my business? (E.g., if one of your values is peace, you might make yoga a priority before you begin your day).

  • What boundaries do I need to establish with my business? (E.g., only working with clients that align with your values, having solid contracts in place with business partners, not working on evenings and weekends, etc).

2. Work on your confidence as much as you work on your business

If you’re struggling with self-doubt as a new entrepreneur, you’re far from alone. It’s extremely common to feel nervous about the journey ahead, but it’s important not to let fear and doubt hold you back from pursuing a business idea that feels compelling to you.

Your business will grow and expand in proportion to your capacity to resolve the resistance and fears holding you back. One of the most powerful ways to combat self-doubt is to look at the limiting beliefs you hold around entrepreneurship and come up with ways to heal or mitigate them.

The questions below will help you address and reconcile the limiting beliefs that hold you back:

  • What limiting beliefs do I currently hold around entrepreneurship? (E.g., I’m worried I won’t know what I’m doing, I’m scared I’ll fail, making money feels hard for me, etc).

  • How might you mitigate your inner critic and affirm your abilities as you begin your entrepreneurial journey? (Think about past times when you’ve felt most successful, and write down evidence and examples that demonstrate how capable you are).

  • What would help you feel more confident as you build your business? (E.g., do you need to read a book on business, write a business plan, hire a coach, learn a new skill, or take an online course)?

3. Decide what a successful career transition will look and feel like for you

There will always be some risk when you start a business, but the right planning and preparation will ensure you feel grounded and stable as you move forward. Your career transition doesn’t have to happen all at once, and it can be helpful to think of your journey in terms of phases. 

For example, if you’re currently employed you might decide to spend the next nine months developing your business on the side while putting part of your paycheque into a contingency fund. When you hit the nine-month mark, you might decide to give your two weeks notice and then work somewhere part time while your business revenue grows. Perhaps six months after that you’ll become a full-time entrepreneur, doing what you love and being well compensated for it.

The following questions will help you map your transition from employee to entrepreneur:

  • What will a successful career transition look and feel like for me? (Think about what will make the experience secure, sustainable, and exciting)

  • How do I want my journey to unfold? (Give some thought to the various phases in your journey from employee to entrepreneur)

  • What support systems do I need to have in place before I become an entrepreneur? (E.g., do you need to find a mentor, join an entrepreneurial community, tell your friends and family how they can best support you, etc).


As you move forward on your entrepreneurial path, remember that you can (and should) feel good along your journey. Instead of burning us out, our businesses should meet our needs and support us in pursuing our highest calling.

If you’re in the early stages of building a business, Bedside Business Plan is a guided journal for entrepreneurs that will help you create a plan for sustainable success. You’re here for incredible things!

Jana Boyko

Entrepreneur and author, Jana Boyko is a powerful guide for anyone walking an entrepreneurial path. Jana has over a decade of expertise and experience coaching entrepreneurs and businesses, from the very small to the very big. Jana is the CEO of a private coaching practice dedicated to holistically supporting people in their transformation from employee to entrepreneur. Her latest book, Bedside Business Plan: A Guided Journal for Aspiring Entrepreneurs, is available at all Indigo & Chapters locations across Canada.

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