Lessons from a Serial Entrepreneur in Business, Love, and Life
“And so for me, it’s very important to have a beautiful balance, and space and time, and just enjoy life.” – Natalie Sisson
A year ago, tears ran down Natalie Sisson’s face as she walked her dogs in the rain. She was stuck in an unusual funk, even though she felt extremely grateful for her life.
As she moped, a voice popped into her head, loud and clear. And it said: “Suck it up, princess.” She laughed, adopting it as her new mantra — and the title of her next book.
Natalie had inspired me to live as a digital nomad with her earlier book, “The Suitcase Entrepreneur.” She was one of the first entrepreneurs I knew who taught me that it was possible to have a life of travel and earn your income at the same time. She continues to inspire me to this day because she keeps reinventing herself. She is uniquely and authentically herself no matter where she calls home or what type of business she has.
In this episode of “Authors Who Lead,” Natalie Sisson talks to me about “Suck It Up, Princess” — its themes of compassion mixed with tough love — and why this book felt so much different to write than her others.
Finding Her Forgotten Heroine
Even though Natalie has always taken big, bold leaps in her life, she found herself wondering what happened to her previous self. What had she stopped doing? When had she forgotten that she was her own heroine?
When we make shifts in our lives, she realized that our inner heroine can get stuffed down — or even forgotten.
I asked Natalie how she was able to rekindle what she thought was lost. She said that “Suck It Up, Princess” is a great start — and a bit of tough love. Sometimes you need a jolt, a behavioral change, or an action that pushes you out of complacency and back on track toward your dreams. Then, you can decide if you want to be the person you once were, or step into a new version of yourself.
As you work through this, you realize that your heroine — that previous version of yourself — is actually still there. She just needs to breathe, despite what’s going on in your life. We tend to forget how capable we are, and that we’re limitless in so many ways.
The only person who truly slaps limits on you is YOU.
Become Your Own Best Cheerleader
Checking in with yourself to see if you need reinventing should be a priority, Natalie tells me.
Working on your inner self is important, and writing a book, especially a memoir, will force you to take a deep dive into your past, present, and future. Humans are complex beings and we need constant reminders and refreshers to be our own best cheerleaders.
As we reinvent ourselves, it’s important to know our “why.” Natalie tells me that even if we’re doing inner work, sometimes we’ll lose our way because our “why” isn’t strong enough. If we don’t know what drives us in life, it can weaken our courage and hurt others on the journey with us.
For Natalie, in wondering how to show others that it was possible to quit their jobs and build online businesses, she discovered her own “why” — which is to help others. With a clear message, she stepped into her courage and her ability to teach about living as a digital nomad, and realized her “why” had always needed to have a bigger purpose than herself.
Taking Intentional Action
Natalie is one of the hardest working, intentional people I know, and she does it with grace and gentleness toward herself. She’s had to regroup and make many changes in her life because she wanted to shift who she was. She believes she is a big action taker because she doesn’t believe there’s much time for anything not to be done.
Sometimes, we can freeze up and not take action at all. Even Natalie is guilty of procrastination — which brings her back to taking the smallest steps possible. When we know our “why” and are intentional about getting out of our own way, this creates momentum.
As I tell my authors, “Inaction is the death of any great, wonderful project.”
Why You Need to Get Uncomfortable
It is important to question our priorities regularly. Sometimes, we remain misaligned because we’ve put in so much time, effort, or money. We think, “I can’t give up on this now.”
But there’s also a time to let go and realize that you, or your life, has changed — and there might be a better fit out there for you. Questioning our “why” can be uncomfortable and scary, but it can also mean you’re on the edge of growth when you step outside of your comfort zone.
How to Choose Your Stories
Natalie’s first two books had great practical tools, tips, strategies, and frameworks. But her newest book felt different and difficult to write, she said, because it shares many personal stories and experiences that she felt would deeply resonate with her readers.
Authors always ask me, “What stories do I keep in my book and which ones do I leave out?” especially when they include very private details, or friends and family members. I asked Natalie the same question, and she explained that her original manuscript had every story she could squeeze in.
But when she had to do a round of edits, she decided to only include the stories that she thought would make the most impact.
Can Imposter Syndrome Be Good?
Imposter syndrome may hold people back from realizing their potential, but it can also be a positive, explains Natalie, who sees people give up on themselves constantly.
Typically, they try something new once and, because they don’t master it immediately, they feel like they’ve failed. But the reality is, it takes years to become an expert.
Natalie tells me that her biggest mission in life is to simply help people tap into their potential — to be their cheerleader. She wants them to know that they need to keep going, and if imposter syndrome sneaks in, that just means they’re close to something special or important.
So, what does, “Get out of your own way,” actually mean, then? Natalie describes it as the simple process of believing in yourself, and continuing to do so. Life is short, and it’s for the taking — and it begins with those small, simple actions every day toward your hopes and dreams.
A Chapter on Love
Natalie has met countless smart, courageous, amazing women who fostered absolute deadbeat relationships in their lives. And while she often wondered why that was, she could identify with them — considering her own romantic history.
In this chapter, she reminds her readers to show themselves compassion. There is a time to go easy on yourself and take time off, and there is also a time for taking action.
As you face discomfort, fears, or imposter syndrome in your life, remember my greatest takeaways from this episode with Natalie:
- It’s time to reinvent the next chapter in your life when you feel the urge.
- Authorship has many stages. Don’t give up on your dreams too early.
- Sometimes it’s hard to say things to yourself. But you need to say them.
What was your biggest takeaway from the episode? How does imposter syndrome show up in your life, and how can it be a positive? Share in the comments below!
That’s all for this week. Love the moment you’re in right now, live life to its fullest, and start writing today!
Book Website: https//:www.thefreedomplan.co