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  • Writer's pictureSamantha Rosenfeld

Five Things I Needed Before Taking the Entrepreneurial Leap

Updated: Aug 31, 2020

When I was a corporate employee, I remember looking at those who took the leap to start their own business with morbid curiosity. I remember thinking, "How in the world can they afford to do something so risky? They must have a nice savings account or trust fund, right?"

Sure, in some situations, people may have the comfortable means to move into small business ownership.

But in actuality, just about anyone can take the leap of faith! It's only up to you whether or not you're willing to take the risks involved - many of which can feel monumental.

For my personal journey, I needed to have five specific things in place before I felt comfortable leaving my corporate career path for things unknown. If you ask other individuals, they may have a totally different view of things.

It's my goal to be entirely transparent about my entrepreneurial journey, which - might I add - is still evolving each and every day!

Here are the top five things I made sure were in place before I turned in my notice and launched my business.


Develop the self-motivation and discipline required to WFH and become my own boss each and every day

Thanks to COVID-19, a lot more people understand just how difficult it can be to work from home. I hope now we can all move away from the idea that it must be so much fun to get to work from home...because in reality, working from home also means you home from work - if you know what I mean.

In my last corporate job, I was able to negotiate two WFH days a week, and the schedule was perfect! A nice balance of meetings and days to buckle down and get the work done. After two years of this schedule, I was able to establish healthy routines and boundaries for my time at home, so I knew I would be able to make a move to the full-time routine.

I also trusted myself to be self-motivated and adhere to self-imposed deadlines as my own boss, since my current role didn't report to a direct manager but rather the president of the company who often allowed me to make my own decisions. That, coupled with my time as a home-schooled elementary and middle-schooler, made me confident that I had what it would take to actually get the work done!

Try the business as a "side hustle" for a few months to make sure it isn't just a phase or hobby

It was almost by accident that I stumbled into my business as a side hustle - a former employer reached out to see if I could assist, and for the right price I agreed to give it a try! From there, I started thinking about expanding my offerings, making a website, pitching ideas to potential clients, and things started to come together.

When I was able to successfully juggle both my full-time role and my side jobs without burning out over the course of six months, I felt ready to dedicate even more of my time towards this business.

Do enough market research to ensure that there is a need and interest in my service offerings

As part of my side-hustle-turned-full-time-gig preparation, I made sure that there was actually a need for what I was offering. I followed other people in my desired industry, watched what they were doing, and mimicked things I liked. I asked my network their thoughts, worked with a business coach to develop my pricing and services, and eventually started pitching myself far and wide to see what stuck.

Once I felt confidence that there was a continual need for what I could offer, I felt safe enough to make a long-term decision for my business.

Establish good financial practices far in advance to prepare in case this goes south

A smart individual will always recommend saving up quite a bit before diving into business - which I completely agree with! However, I personally found it essential that I have strongly developed financial practices so I could trust myself to run a business. That meant exploring the world of business accounts and taxes, and all of the other scary things!

I also invested in a bookkeeper. 10/10 would recommend if you dread numbers the way I do!

Ask and receive my personal network's support of this decision, including my significant other

Perhaps the most important step for me was saying my business idea out loud and gauging my personal network's reaction to the concept. I made a bet with myself that if it was overwhelmingly cautious or unsupportive, I'd table the idea for another year.

Yet every family member or friend I floated the idea past was so supportive - to the point that they were pushing me to make the change sooner rather than later!

What sealed the deal was my fiance's support - when he got excited about the idea, I knew I could do it. In the end, it was people's faith in me that allowed me to take a dream and make it a reality.

In honor of being transparent, I will share that without my spouse's medical and financial support, my decision may have been different. I am grateful every day for his support in this dream, and I recognize the privilege that accompanies my ability to be an entrepreneur.


That being said, none of this journey is easy. None of it. I wake up most days dreading my email inbox, anxious over meetings and projects. Impostor syndrome follows me around, day and night.

But that's a conversation for next time.

Curious about any of this? I always welcome a dialogue and love to connect with individuals who are considering a change. Feel free to send me any questions you might have at

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