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I'm Kelly - the founder of She Is Fierce! and your host on our blog featuring stories and wisdom from fierce women all over the world! 


#41: Summer School: How to Get Started In Your New Business or Side Gig

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I’m back with week two of our summer school series – inspired by She Is Fierce’s sister company – Heirloom Leadership & Learning Co.

Throughout July and August,  I’ll be highlighting some of the lessons I’ve learned from building She Is Fierce! and some of the skills we teach through our sister company Heirloom – many of which you have access to in our She Is Fierce! Membership.

Throughout the summer, I’ll be answering some of the most common practical questions I get at events and in private consulting sessions on building your business or career.

But don’t worry – we’ll be back with more amazing interviews with fierce women in the Fall!

Last week, we talked about how to find your passion and purpose… and build a business or career that you love.

Now, I like to keep my focus on mission-driven businesses led by women who want to make a difference in the world – whether that difference is simply making enough to sustain their families doing what they love or launching a product or service that will help others improve their lives – or even starting nonprofits with a clear mission to serve.

That focus on women with purpose and their mission-driven lives and businesses means that I will be giving you some very practical advice, but with the specific goal in mind of helping you succeed at doing something that you are proud of – and taking some of the struggle out of your success.

This week, we’re going to go into further detail into one of the most common questions I get from friends, strangers and community members – ‘How do I actually start?’

So, I’m going to break down the practical steps I believe you need to take to get started in your new business or side gig, and I’ll share some of the challenges I experienced and overcame along the way.


# 1 – Don’t Quit Your Day Job – Yet

#2 – Know Your Motivations.

#3 – Make a Plan

#4 – Think About MONEY.

#5 – Remember that Hard Work is Inevitable 


Ok – let’s go deeper on these four steps to success when starting your new business or your side gig…



#1  – Don’t Quit Your Day Job – Yet. There are two exceptions to this and I will explain those too.

First, I know this advice can be SO frustrating when you’re SO ready to just get started and have a clear focus on doing the thing you’ve been dreaming about… and it may seem counterintuitive for me to talk about ‘how to get started doing something new’’ by saying ‘don’t quit the thing you’re already doing.’  

But here’s the thing – I want you to be successful at this new thing – not just start it. And putting financial pressure on your mission-driven business or sidegig to immediately replace your current income and cover expenses and allow you to think about growth opportunities is almost always unrealistic.  And, it’s why almost half of all businesses don’t last beyond the first five years.


Let me explain my logic further.

First, understand that we all start from different places.

It’s not fair, but it’s reality, and the more time you spend wishing you had what someone else has, the longer it will take you to get to where they are.

That isn’t to dismiss the extra struggle – it’s truly to say, I fully recognize it… in my own experience and working with so many women, I see where I have been so lucky and started ahead of many, and also behind many others…

To show you what I mean, I’ll share a little of my own experience – and you may see some parallels or differences in your own life.

First of all, here is how I started ahead of many:

  • I began my business when I was married to a person who was bringing in his own salary.
  • I had a master’s degree from a prestigious university and high-level professional experience working for internationally recognized companies.
  • I knew that if things didn’t work out, I would be ‘ok.’  I would be incredibly disappointed, I might be embarrassed or have to account for time on my resume, but I wouldn’t be worried about feeding my children.


Here’s how I started behind many:

  • I started my business as a mom to two young children – an all-encompassing job of its own… which meant I was basically learning how to ‘mom’ and how to ‘business’ at the same time, and often feeling overwhelmed at the sheer amount of work to stay afloat in both areas.
  • I didn’t have any investors or any money set aside to start a business with – and I mean that literally… I put the first year of expenses on a credit card, tried as hard as I could to keep expenses as low as possible (which slowed me down a lot in the beginning – but ultimately helped me grow a business that is still around eight years later) – and prayed things would work out so that I would be able to pay everything off… and making money would be a miracle!
  • Finally, I didn’t have a clear plan… that thing I just said about ‘making money would be a miracle’ – I mean that.  I really started She Is Fierce! as a passion project hoping to find work doing something meaningful to me. But when I say I can give you the best advice on how to succeed early on, it’s based on working personally with hundreds and ultimately with thousands of women starting something new – but also on all the things I did right – and wrong – like not having a real money-making plan when I started out.


Your circumstances are likely different, but I’m sure some people listening will hear my example and think ‘well, I’m already so far ahead of where she was – I have money in the bank or investors already lined up.’  

Others may hear it and think I am incredibly privileged and no wonder things worked out for me – I didn’t have to worry that failure would mean homelessness, and I had a career I could go back to if things didn’t work out.

And both responses would be right.

That’s the point.

You have your own unique set of circumstances, and you have to decide when you are ready to give up the security of your current income and put all the financial pressure on your business.

I would encourage you to do that once you are already making money in your business and you have a money plan in place – not when you’re still in the excited ‘figuring things out stage.’

My dream for you is security and success – not success after years of financial and emotional struggle… and certainly not failure.  You have so much to offer and your skills, talents and mission deserve time and space to thrive and grow.

Here are the two exceptions where I would say, ‘Go for it – and use all your energy on your business now,’ if you came to me asking for help in figuring out how and when to get started.

Here are the two unique and unusual categories you might fall into where I would go against my general advice and say, ‘don’t keep your day job!’

One – you are independently wealthy and have that clear sense of security, no matter what happens 

Two – you are currently unemployed (maybe you just recently lost your job) and you do have some savings in the bank or a spouse you can rely on/a couch to sleep on until things start to pan out. 

Being able to focus your energy solely on your business will help you make more progress up front – but only take this path if you can afford to struggle a little getting things off the ground! 


#2  Know Your Motivations

I’m going to keep this one simple – because it is.

Basically, make sure you do a real ‘gut check’ that you are pursuing something you’re willing to do the work – and I mean a LOT of work – to bring to life.

Imagine some scenarios – what if you become wildly successful and your business becomes everything you dream it can be ? That would be amazing right?!  What if that is still true – but it takes ten years? Would you still want to get started because it means that much to you?

What if you are rejected by the first 20 people you pitch as clients or customers? Will you have the certainty in your heart that you’re on the right track?

Yes?!  Wonderful – WHY? 

It’s ok to be unsure and it’s absolutely ok to make changes and shifts and grow along the way – but I want to be sure that this new business or project you’re going to take on ties back to your sense of passion and purpose – and that you’re clear on WHY you are doing it.

And by the way – it is totally ok if that reason is to make money or to prove something to yourself or to any of a million other reasons that might not seem like ‘enough.’  But those reasons (any reason) is only ok if your ‘gut check’ says ‘this is enough to sustain me – and this matters to me.’ 

If you’ve got a dream and you have that ‘gut check’ down, you’ve got more than enough to keep going… now it’s just about doing the work.

So, let’s talk about some of the first work you should do:


#3 – Make a Plan.

You don’t have to have a formal business plan to get started, and again, it truly depends on your personal style how much structure you want to build before you get started.

I’ll share some more details on many of these things along the way and we have resources on them available within the She Is Fierce! Membership, and more coming… BUT, here are some items you need to consider right away:

    • Write a business plan.  It doesn’t have to be a complete ‘investor-ready’ plan, but it does have to cover some of the basics:
      • What exactly will you do?
      • Who is already doing this in the marketplace?
        • What can you learn from their successes and failures?
      • How will you fund your business?
      • What legal / financial things do you need to do to make sure you’re covered once you’ve started to make money? These might include things like registering your business name, getting federal and state tax IDs and making sure you have any trademarks or other legal protections that apply to your business.


#4 – Think About MONEY.

Most mission-driven business owners I meet in the first couple years of business are struggling – not because they don’t have incredible skills or products, not because they don’t deserve to be paid well, but because they are so focused on the mission that they actively work against themselves.

Here is a phrase I have heard countless times from new business owners or even women years into business who are still struggling to bring home any meaningful amount of money:

‘I don’t even care about making money, I just want to help others.’

Honestly – you guys are incredible, fierce-hearted people and I have so much love and appreciation for you – and for every woman who has ever said that to me… and I have to include myself in that group when I first started She Is Fierce!

When I first started, I had a brand new baby and a two year old – and I wanted to find something to do to keep my brain busy and keep me feeling fulfilled professionally and personally, while also having time to to be present for my young children.

I WANTED the work to make money, but I didn’t have a PLAN to make money… so guess what? I didn’t – or actually, I did bring in some money (not much), but I had an equal amount in expenses… I think you can see how that story ends.

So after a year of incredibly hard work doing something that felt really important and exciting – while also being a full-time mom – I was left with no financial benefit to contribute and the prospect of spending more money to keep the mission going.

That was a low point for me – wondering if I could turn this incredible community and a series of successful events and programs I had created into something I could sustain and actually do after what I had been considering my ‘very busy extended maternity leave.’

I realized that if I wanted to make a DIFFERENCE, I would also have to make MONEY – otherwise, I wouldn’t be able to continue to do that meaningful work.

That shift in perspective changed how I ran the business and how I approached sales.  I want to make a difference for the women in our community, and I can only do that if I can also make a living and pay the wonderful people I work with, the vendors for our events and the expenses to keep it all going.

And the same applies for you. Having the sense of financial security will give you freedom to do work that matters to you – and to think about opportunities objectively and make growth-focused decisions!


And finally,  #5 – Remember that Hard Work is Inevitable – and sometimes failure and struggle are actually a sign of progress!

I have to be honest with you here – no matter what – even if you’re making a profit in your business right away, you will struggle with something – probably many things.

And that’s ok.

And, it’s absolutely ok to be afraid of failure – but remember that those who are most successful are often those who fail the most too… but they just don’t brag about their failures, so you’re only seeing their highlight reel.

The most important part of overcoming struggle is taking time to assess what went wrong and what went right – and do more of the latter!

The success you find in your new venture will be even sweeter because of the hard work you put into it!


So, let’s do a quick recap…


# 1 – Don’t quit your day job – yet

#2 – Know your motivations.

#3 – Make a Plan

#4 – Think About MONEY.

#5 – Remember that hard work is inevitable 

You have SO MUCH ahead of you – and I truly cannot wait to hear about the impact you make in the world!

Remember, we have resources within the She Is Fierce! Membership to help you get started, we have a phenomenal group of women business owners in our CEO Mastermind Circle, which will be re-opening this Fall, and I am opening some spots to meet with myself and our team leaders this Fall as well… so if this podcast inspired you and you’re looking for a little extra help and support on your journey, reach out to us at

We’ll help you find the best path for you – whether that is with us or with other women in our community who can help you with specific challenges!

Wishing you inspiration today as you think about your next steps – and ultimately success on your new business journey!!


Ready to jump in?

On our Five-Star-Rated podcast, you’ll hear the inspiring stories of fierce women who have overcome challenges and built purpose-filled lives. Over the coming months, we’ll be sharing interviews with some of my absolute favorite past She Is Fierce! Speakers and our incredible members. Kelly will also be dropping in for some solo episodes to answer some of the questions she gets asked regularly about how to grow a powerful brand, how to build a mission-driven business from scratch, and how to find joy in the journey. Tune in, rate and review the podcast, and let us know who you would love to see us feature in the future!

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