Leave Your Job To Start Your Own Business

Self StartHER Tips


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Founder, Self StartHER

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Let me guess…You have a burning desire to leave your job to start your own business. 

This burn is so hot that it’s all you can think about 24/7. But, you have some hesitations. Thoughts consume you like…

“What would I even do”?

“What if I fail?”

“What will my family and friends think?”

So many “whats” that all come from a place of fear. 

But, guess what – understanding and preparedness can help take some of this fear away. 

How do I know? I’ve been there.

And, I’ll be sharing some questions to ask yourself when you are contemplating your next move. Hopefully these questions will eliminate some of these fears and help you understand when it’s time to leave your job to start your own business.  

Let’s get started!

Question #1: Why do you want to leave your job? 

Before making the leap to start your own business, it’s important to reflect on why you want to leave your current job. Are you driven by a genuine passion for a new venture, or are you simply unhappy in your current role? Understanding your true motivations can help you make a more informed decision.

Start by considering your current job satisfaction. Do you feel unfulfilled, undervalued, or constantly stressed at work? If your primary reason for leaving is dissatisfaction with your current job, it might be worth exploring other career opportunities or making changes within your current role before starting a business. Sometimes, the desire to escape a negative work environment can cloud your judgment, leading you to make impulsive decisions.

On the other hand, if you have a burning passion for a business idea and find yourself constantly thinking about it, that’s a strong indicator you might be ready to make the switch. Ask yourself if you’re excited about the challenges and opportunities that come with starting a business. 

Reflecting on your motivations helps ensure that your decision to leave your job is based on a genuine desire to build something new, rather than simply escaping your current situation.

Question #2: Are you financially prepared? 

When money is tight, decisions tend to be made out of a state of lack – and, your business will feel that. 

With that being said, I always recommend having a hefty sum set aside (ideally enough to cover one year of your expenses) OR beginning your business while you are working a full time or part time job. 

Most of us will have to do the latter because, let’s face it…life’s expensive! 

Yes, it’s more work at the beginning to juggle both your job and your new business, but there is a plus here…

Not only will that job allow you to sleep a bit better at night knowing that your bills will be paid, but it also will help finance your new endeavor. 

A win/win, right?!

Question #3: Is your business idea viable? 

Before you jump all in, it’s best if you do a bit of research to make sure that your business idea is one that has the potential to be successful and make you money…assuming that’s the goal. 

Start by figuring out who your target audience is and what they need or want. Look at your main competitors to see what they’re doing right and where you can do better. 

Next, you need to validate your business idea. A simple way to do this would be to talk to potential customers and get their feedback through surveys and interviews. This will not only help you get into the minds of your target audience, but will also help you identify any issues before you go all in.

While this step is important, I do want to insert an asterisk here because some people spend too much time on this step, overthinking every little thing, and it prevents any real action from being taken. 

Question #4: Do you have a support system? 

Starting a business is not easy. If it were, everyone would be doing it. 

You will have days where you feel on top of the world, but others…well, let’s just say you may need some help lifting your spirits. 

That’s why it’s so critical to have a support system in place. But, you may find that the people closest to you aren’t always going to be able to provide you the kind of support you really need. 

So what do you do? 

You find these people.

Join Facebook groups. Follow like minded people on social media. Have conversations with these people – heck, even grab a virtual or in person coffee! 

A group that I have really enjoyed and that I highly recommend for women starting a business (because there is a free component to the group!) is Like Minded Collective.

Lastly, seek out a mentor(s). Someone who has been there before that you can learn from and go to when you need a bit of a pick me up. 

Question #5: Do you have a business plan? 

Your business plan doesn’t need to be overly complex, but it should clearly outline your goals, strategies, and financial projections. Start by defining your business goals and the mission of your company. What are you aiming to achieve and what values will guide your business?

Next, outline your strategies for reaching those goals. This includes your marketing plan, sales tactics, and operational plan. Think about how you will attract and retain customers, what channels you will use to market your products or services and how you will run the day-to-day operations. This part of your plan should also include an analysis of your competition and how you plan to stand out in the market.

Lastly, focus on the financial aspect. Estimate your startup costs, ongoing expenses, and projected revenue. Include a break-even analysis to show when you expect your business to start making a profit. Having a clear financial plan helps you understand the viability of your business and can be crucial for securing funding from investors or lenders (if that’s something you’re interested in going after!). 

A well-thought-out business plan acts as a roadmap, guiding you through the early stages of your business and helping you stay focused on your goals.

Question #6: Are you ready? 

Assessing your personal readiness is crucial when deciding to leave your job and start your own business. You need to make sure you’re mentally, emotionally, and physically prepared for the journey. Starting a business can be incredibly rewarding, but it also comes with a lot of challenges and uncertainties.

Begin by evaluating your tolerance for risk and uncertainty. Are you comfortable with the idea of not having a steady paycheck or the security of a regular job? Consider whether you have the discipline and motivation to stay focused and work independently, especially when faced with setbacks or slow progress. It’s also important to think about your support network—do you have friends, family, or mentors who can provide guidance and encouragement along the way?

Finally, reflect on your personal lifestyle and commitments. Starting a business often requires long hours and a significant time commitment. Are you ready to balance the demands of a new venture with your personal life? Making sure you’re mentally and emotionally prepared will help you navigate the ups and downs of entrepreneurship with resilience and confidence.


To wrap it up…

The decision to leave your job to start your own business is HUGE and should not be taken lightly. 

But – it’s also SO exciting and something that personally gets me fired up. 

I hope these questions to ask yourself help take away some of the fear in starting a business and get you closer to taking the first step.

About the Author:

Megan Tobler is the founder of Self StartHER, a fast growing podcast and community for aspiring female entrepreneurs, aka “Self StartHERs”.  Through engaging conversations and insider tips from industry leaders, she offers invaluable resources and unwavering support, helping women launch and grow their businesses with confidence. With her infectious enthusiasm and unwavering dedication, Megan is on a mission to empower women to turn their entrepreneurial visions into reality. 

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