Story 14 | 3 Strategies For Embracing Risk
To help you prepare for a noteworthy new year, I'm sharing my time-tested strategies for embracing risk, so you can dream bigger and execute better in 2025.
Happy New Year!! It’s January 2, so we’re dipping our toes back into real life after the escape of the holidays. If you are a dreamer or a planner, maybe you have some ideas on what you’d like to make happen this year. Or maybe you want to be more of a dreamer or a planner!
Either way, to offer some motivation and concrete tips on HOW to make your year awesome, I give you this article on how embracing risk isn’t actually reckless or dangerous but can prove immensely fruitful. Taking risks has made my life rich, and through practice, it’s not something that scares me anymore.
Cheers to an exciting year ahead!
3 Strategies For Embracing Risk
“And now let us welcome a new year – full of things that have never been before.”
- Rainer Maria Rilke
What a difference a year can make.
At the beginning of 2024, I was working full-time and then some, managing the sale of my company so it would go through smoothly, and staring down the gauntlet of having to tell my beloved team and clients about my transition out of the business. I was hoping to get pregnant as a single mother by choice, having already completed three unsuccessful rounds of IUI in 2023.
By the end of 2024, I completed the sale of the business and transitioned my work, team and clients, with relatively few bumps along the way, happily. I traveled rather extensively, visiting Paris, Harbour Island, Ireland, the Dordogne and Los Angeles. I started pursuing getting published as my new full-time career, including reviving my creative habit by launching this email newsletter releasing one new short story a week, committing to a social media strategy and preparing to work on my novels. Not only did I get pregnant this year – lucky round five! – I welcomed my daughter in the month of December.
What a difference a year can make. My life is almost entirely different, professionally and personally.
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As you consider the year ahead, what do you want to accomplish? How do you want your life to look at the end of the year? What sticking points from the year before do you want to address? What new visions do you want to bring to life? How will you make this happen?
I believe you can make it happen. There’s a nuance here: it’s more than just taking action. We all know how to take action. Where we hesitate or stumble is we get nervous or scared in the moment – which is fair. So, how does one overcome the fear of taking action?
My secret is learning how to embrace risk.
There are a couple ways one could look at the moves I made in 2024. The risk-adverse might say I walked away from a successful company that provided me with financial security to pursue a career that may never produce a paycheck. All while growing my family and increasing my expenses. They might say these are scary, unnecessary risks for me and my family. I see their point, but I don’t view these moves as scary or unnecessary.
I view it as chasing my dreams. For these dreams to happen, I have to take some risks. I couldn’t run my company, write books and be a mom – there aren’t hours enough in the day. So, I assessed my priorities and determined I would regret not fully trying to get published. I’ve journaled this same line for decades (yes, plural): I WANT TO BE A WRITER. Just like that, in all caps. If not now, then when? Same was true for baby. I was turning 40, and based on my tests, my fertility doctor suggested it would close to impossible for me to conceive past 42. I love kids, and countless people have told me that having children is the greatest joy of their lives. Sounds amazing, sign me up. Oh, I’m not married and short on time? I want it enough, I’m willing to accept the risks.
Embracing risk allows you to dream bigger and execute better. If you’re not afraid to take risks, more things become possible. If you’re not afraid to make changes, you become more open to making your dreams a reality.
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As you prepare for your year ahead, whether you’re considering massive transformation or small meaningful changes, here are three concrete strategies to make taking risks more approachable and replicable for anyone. I hope this provides some powerful motivation and makes you feel like you can do it!
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RECKLESS —> PLANNED
Risk is commonly perceived to be reckless – ie, a lack of concern for the consequences of one’s actions. Think people performing wild stunts or making wild bets, ignorant to the realities of gravity, their own mortality or the odds around a situation.
Most of us care about the consequences of our actions. We think things through, and as a result, we see the ways things can go wrong, so we get scared and bail.
Yet, risk doesn’t have to be reckless. Risk can be planned – meticulously planned. Consider skydiving: as if I threw my body out of a plane without thinking about it first. Rather than writing off a risk as purely foolhardy, you can break it down and find a way to make it not only tenable, but smart.
My most successful risks came from careful study and planning. When I decided I wanted to move on from my company to write books and start a family on my own, it was (and is) an enormous risk. But it was also carefully planned, which increases the odds of success. I didn’t just quit on a whim and gather myself to start writing a book from scratch. I researched the best ways to exit the company. I plotted a marketing strategy to implement while I edited drafted novels and prepared to secure an agent. I budgeted to ensure I could support myself and a child.
Planning for major risk can and should take months. Typically, I’ve needed three months to clearly figure out what the move was going to be, then another three months to practically prepare for making that move. In case of selling a business and preparing to be a parent, it was well over a year.
Because I planned and I prepared, my leap was purposeful and productive. I had a direction, a goal and a means to get there. It was still extremely risky, but it was no longer reckless. Planning makes risk less reckless and sets you up for success.
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INSECURE —> CONFIDENT
Risk is made more tenuous because you don’t know what’s going to happen. There are no guarantees on the outcome of your gamble. Risk inherently preys on your insecurities, making you play mind games with yourself, from imposter syndrome to planting seeds of doubt. You will repeatedly question yourself and how wise it was to put yourself in this situation.
The antidote is to build up your confidence. Risk is working to undermine you, so here are two tips for fighting back with confidence.
First, in that moment of risk, lean on your track record. Think back over your experiences. Moments where you’ve exceled in your career or your sport. Silly things like your grades in high school. This reminds you that you’ve done well before, and it stands to reason that you can and will do well again.
When I look back, I realize I have a habit of landing on my feet. My track record is strong. I tell myself, when I take this next step, when I take on this new challenge, I will do well again. I take my confidence back.
But let’s say that you don’t have that track record or it’s simply not enough for you. You get better at taking risks the more you do it. Start with something small to get your footing: sending a cold email, asking for something you want. Over time, you can flex that new muscle and move on to more meaningful risks. Over the last few years, I’ve realized that I can risk bigger now – I’ve developed a confidence in taking risks.
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DANGEROUS —> COURAGEOUS
Risk is dangerous.
Here’s the X-factor. As much as you plan and as confident as you might be, that only takes you so far. There’s no sugarcoating it: risk is dangerous. At some point, you still have to jump – into danger, into discomfort, and without a guaranteed outcome. That is risk.
So, take courage. The quote I always come back to is: “have the courage of your desires.” This quote makes me confront why I’m considering a risk. The reason why you jump is because of what’s on the other side. Any time I have taken a risk, whether a career move, a physical feat, a personal declaration, it comes down to digging deep and saying “I want that – despite the odds, despite the obstacles, despite how unlikely it might seem, despite how much I might lose, despite never have done something like that before, despite everything. I want that. It is important to me. It is worth the risk.”
If you want it, if you want to live a bold, rich life, you’ve got to go get it. You have to have the courage of your desires.
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Bottom line: I think risk is awesome because it makes my life meaningful. I have to take risks to get the things I want, to live out my priorities.
For 2025, I’m going learn how to be a mom, land an agent and publisher, and buy a house. I’ve been intentionally laying the foundations for these moves for a while now. None of these things are guaranteed – agent and publisher, in particular – but I now appreciate the thrill in the challenge.
This year, how might embracing risk create new opportunities for you or enrich your life? I’m excited to see how risk will pay off for you.
Thank you so much for reading! Your feedback is welcome: rate the story with one click in this poll, or get a discussion going in the comments.
TELL ME THIS: what goals or risks are you considering in 2025? Please share with us so we can cheer you on. What obstacles do you foresee that are holding you back? Hopefully nothing, but if so, maybe I or another reader can suggest a solution?!
Next Week’s Plot Twist…
I’m sharing a chapter from one of my unfinished novels, this one delving into the flashy and grubby life of NYC public relations and socialites. A junior PR girl is mistaken for an heiress-in-hiding and quickly realizes it’s a set-up for something more sinister.
Last week’s story:
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