5 Mistakes to Avoid When You're Considering Taking the Leap Into Entrepreneurship

Wondering if now is the right time to take the leap into entrepreneurship?

Listen for mistakes to avoid and tips for dealing with these common roadblocks, then be sure to check out our NEW Before You Leap Mini Course.

We're in a moment right now where it seems like everyone is an entrepreneur or considering becoming one. Stepping out on your own has become the sexy thing to do.

But I think it's really important heed the wisdom of our elders and “count the cost” of exactly what that transition from employee to entrepreneur might look like and be more thoughtful and strategic.

Many of us are at points in our careers where we have responsibilities: a mortgage or two, student loans, children, caring for yourself and nurturing other loved ones.

From the many different places most of us mid-career professionals sit, we don't have the luxury of just leaping and figuring it out later.

That’s just not a thing in our world.

So it's really critical that we get strategic, be thoughtful, reel that passion back a little bit, slow down and truly consider exactly what this transition looks like.

To help us out, I'm going to share five common mistakes that I often see aspiring entrepreneurs make and how to avoid them.

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Mistake #1: Forgetting how dope you are

One of the things I'm always so surprised to hear women say when they are considering stepping out on their own is, “What could I possibly have to offer to the market that might be a value? What would people even pay me to do?”

This, even though they are often very well paid in their corporate jobs doing work that people clearly find valuable.

It’s tricky.

When we’re too close to our accomplishments and talents, it can be hard to see them. We’re often really critical of ourselves and don't really see often the special sauce that we bring to the table.

And don’t get me started on the socialization that often results in us shrinking back from speaking up and owning our skills.

Try this: In addition to doing your own self assessment, consider tapping into your network of friends and colleagues who really know you well. People who love you and who've known you over time can often give insights into exactly what it is that you bring to the table that others don’t have.

Mistake #2: Focusing on the “what” MORE THAN THE “why”

The second mistake I see people make is starting out too focused on the “what” instead of the “why.” New entrepreneurs often get annoyed and fight me on this point at first. Then, almost without fail, they circle back later and realize it’s sound advice.

People get so in the weeds about the tech, website, logo, business name, branding, etc., at which point starting a business can get incredibly overwhelming. When you're first starting, try to resist diving headfirst into the “whats” of business.

Sustainable businesses are first built on a solid why.

One of my favorite books is by Simon Sinek: Start With Why. His premise, after having studied several businesses, organizations, leadership structures, military science, etc. is that the way that businesses really succeed and make a lasting impact are the ones that start with why and not the what.

In the book, he gives the example of Apple. Have you noticed their billboards and commercials don't really talk about the specs and the tech of their computers until they first hook you in with a story that gives you an experience of why it even matters? They lead with how that technology is going to make you feel, and then they follow with the tech.

Try this: So think about why in two ways: think about why you are interested in entrepreneurship. Are you a necessity entrepreneur (you need to move forward in entrepreneurship because of your financial circumstances). Are you an opportunity entrepreneur (you see a gap in the market and you want to fill it)? Or are you a flexibility entrepreneur (you want to have the freedom to work and live on your own terms)?

Really get clear on why you're moving forward in this direction so that you can stay grounded in your reasons and use them as a compass to guide some of your decisions moving forward.

Of course, this applies to your business directly as you start crafting your offers and figuring out what your business will be. You really want to get clear on the why for your businesses and make sure that you're communicating not just what you offer, but the story and meaning behind why that service is important to the people that you serve.

Mistake #3: Reacting instead of creating

The third mistake that I see people make when they're considering leaving their jobs and working for themselves is coming from a reactionary perspective instead of a generative and creative perspective.

I posted a statement on Instagram recently that seemed to really resonated with a lot of people: Entrepreneurship is not a cure for job dissatisfaction.

It’s true. It may lead to and be a tool of personal fulfillment, but it can’t only be that. Entrepreneurship isn’t just a thing to do when you don’t like your job.

Job discomfort can certainly nudge us and get us out there faster with fire in our bellies and under our butts. But that alone is not a reason to go into entrepreneurship—at least it can’t be the only one. If you don't have a solid business model that meets a need in the market, you won't be in business for a long.

Try this: Consider coming from a generative place and a creative place instead of just a reactionary place where you're mostly leaping into entrepreneurship because you hate your current situation. Assess where you are right now and develop an intentional plan and goals for exactly what entrepreneurship is going to create and generate for you and for others.

Mistake #4: Not knowing your numbers

The fourth mistake that I see people make, especially those who might be like me—liberal arts, English major types—is avoiding looking at the numbers. Math has never been my thing, and maybe it hasn’t been yours. But as business owners it just has to become our thing.

Try this: Friend, you need to run those numbers. You really need to know exactly what your revenue goal should be and how you're going to get there. A lot of times people think their business should be aiming for their work salary to make an even exchange.

Not so.

There's so many other factors, expenses (and write-offs), investments and more that come into play when you're a business owner that aren't really in the picture when you are an employee. The Income Clarity Spreadsheet inside Before You Leap is a tool that I've created to help you crunch your own numbers and think through your revenue goals.

Mistake #5: Going it alone

Entrepreneurship can be a lonely endeavor and a lot of times we don't have others immediately around us that are doing it. On the one hand, it feels like entrepreneurship is like in the zeitgeist and everyone is doing it, then we turn to our immediate local communities and it can feel a little lonely.

To the extent that you can, build in time for community. Seek out connections. Particularly look for people that are what Lacey Phillips of To Be Magnetic calls “expanders”— people who, as much as possible, reflect similar things about you but are doing what you want to do in the future. From a neural pathways perspective, seeing expanders starts to train your brain to think that what you’re going after is actually possible for you.

That's why representation matters. That's why diversity matters. That's why images matter. That’s why visibility matters.

It matters for you, personally, but it also matters for others who will look at you and say, “She did it, and now it’s possible for me, too.”

Try this: Research industry conferences that are related to your field. Join relevant Facebook groups and deepen those connections offline. You can also identify “imaginary” mentors and friends. If you admire a business owner from afar, research and reverse engineer their interests. Learn from the breadcrumbs they’ve left along the way.

Join my NEW Self-Paced Mini Course
Before You Leap
Available for Early Enrollment Now

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In this mini course, you’ll work through the exact questions and prompts I’ve used to coach myself and others through making the transition into entrepreneurship.

Go from “maybe-preneur” to absolutely sure about whether or not entrepreneurship is the right step for you.

Before You Leap is an easy-to-digest, practical course that you can get through in about an hour. Inside you’ll find:

  • Step-by-step lessons that walk you through: 

    • How to assess your most marketable skills 

    • How to determine what type of entrepreneur you are and the steps you should take (and avoid) most immediately

    • How to set clear goals and intentions for your shift into entrepreneurship and minimize the likelihood of regrets 

    • How to leverage your 9-to-5 now and add value to your employer before you make the leap

  • An expanded 30-page workbook with practical exercises to help you put each lesson into practice

  • A done-for-you income clarity spreadsheet to help you map out your income goals

  • Lifetime access to the mini course and any future updates

The course will go live on Saturday, June 15. Right now early enrollment has just opened, and you can grab the course now for $50 off, which is just $47. I wanted to make it a no-brainer and an easy yes for you to take this foundational step and be thoughtful about your entrepreneurial goals. Don’t wait to grab your seat in the course because the price jumps up to $97 on June 15th.