36. Normalize the Risk: 7 Lessons from Jenn Drummond on Setting Impossible Goals

Episode #036

Sendy Mom Jenn Drummond World-record holder, mom of 7, and motivational speaker

The beginning of the year is a great time to set new, ambitious goals. I am a dreamer. I like to set big, hairy, audacious goals. The unlikelihood of success does not deter my attempt. I really like thinking about the what-ifs.

If you want to learn how to do this more effectively in your life, read on.

Taking risks can be uncomfortable. I’m not talking about risks that take your agency or someone else’s away; like drugs, alcohol, pornography, or gun violence. I’m talking about calculated, trained for, physical or mental risks that challenge you and help you grow into a better person. Risking feeling tired, sore, nervous, embarrassed, or defeated can be temporary results that if dealt with properly can turn to feelings of strength, power, alertness, confidence, and high self esteem.

After a near-fatal car accident, Jenn had a good look at her life and decided she wasn’t living up to her potential. She decided to get uncomfortable. She didn’t grow up climbing mountains. She started in her 40s, having never slept in a tent. With no experience, Jenn went on to become the first woman to summit the second-highest mountain on every continent, while raising 7 children as a single mother.

In honor of the number 7 which seems to be Jenn’s number, I am sharing 7 powerful lessons from our conversation. I think it’s interesting to note that the number 7 in Hebrew scripture symbolizes completeness, wholeness, and sacred fulfillment.

These lessons will help you normalize risk-taking, set goals that feel impossible, and model a life of thriving for your children.

1. If You Want Your Children to Thrive, You Must Model Thriving

We often think that being a “good mother” means doing things for our children; serving them, helping with homework, packing their lunch, getting them a job, helping them get into college, find a spouse, watch their children while they are at work, and give them advice about life.

If this is what brings you joy, knock yourself out, and make sure your kids see that all of this is your version of thriving by being excited about it.

Stop the guilt. You are not a “bad mom” if you don’t want to play with your children, cook gourmet meals for them, write term papers for them, find them a job, put together their Bumble or Hinge profile, or write up their resume. There are other ways to form connections with your children. And you should find what works for you and them. Being self-sacrificing does not mean you sacrifice your happiness for theirs. In fact, that will most likely backfire. Energy is contagious. Make sure your energy is positive by finding something that really lights you up.

Don’t be neglectful of your children, just be deliberate.

“When you know you’re going to be gone, you’re more intentional about your time before you leave.”
Jenn Drummond

Thriving is taught by example. If you want your children to thrive, you have to live your life, not theirs. It is amazing how much they can pick up from where you get your joy. If they see you getting excited about your big, hairy, audacious goals, they will want to set those goals too.

No amount of lecturing will persuade a child that you are happy with your life. They need to see you doing it.

What are you doing to thrive right now? Can your kids see how happy you are doing what you love? Have you had to give up some of the things you thought were “good parenting” in order to do some of the things you love?

2. Every Challenge Becomes Possible When Risk Is Normalized

“When you’re in an environment that normalizes taking risks, you do it because that’s what’s normal.”
Jenn Drummond

Risk feels terrifying when it’s unfamiliar. Our human brains want to do what is easiest. But when you spend time in environments where challenge is normal, fear loses its power. Even if you weren’t raised in this environment, you can push and challenge yourself a little at a time until the risk is worth the reward.

Jenn talked about how Everest became “normalized” for her—not because it was easy, but because she was surrounded by people who treated it as achievable.

If everyone around you avoids risk, your goals will always feel impossible. Surround yourself with people who try.

Normalize the challenge, and the challenge shrinks.

What risks could you normalize in your life? How can you help your children feel more capable? Who do you know who has accomplished the goal? Why can’t you do it too?

3. Choosing a Challenge

If you wait around long enough, challenges will find you. I’d rather choose my own, thank you. I don’t like wasting energy on things I can’t control like politics, what a family member said or didn’t say, or what my neighbors think.

If you’re like me and enjoy being in charge of your growth and development, here are a few suggestions from my conversation with Jenn about how to find a challenge that suits you:

Ask your kids, friends, family members what they think you should try
Make a list of ideas. My husband and I have a shared note that we add to when we get inspiration.
Look at world records or unusual accomplishments.
Have a conversation with somebody and ask them questions instead of talking about yourself. Ask about their favorite vacation places, what they’ve done that has scared them, or what they are excited about.
Browse these Sendy ideas and see what sparks curiosity
What are your priorities. Align your challenge with your priorities
Choose to do a challenge with friends or family. You could do a sibling challenge like Carmen Hall does each year with her siblings.

Choose a challenge on purpose. Put it in your calendar today. If you don’t schedule the fun, it likely won’t happen.

What idea excites you? What can you start before you know everything? Is there something you can prepare for as a family? If you didn’t have to worry about what people were saying about you, what would you spend your energy on?

4. Find a Coach

When Jenn decided she wanted to climb a mountain, she found somebody who had already done it and hired him to help her “normalize” climbing the tallest mountain out there.

If you don’t have the money to hire a coach, there are books, articles, movies, and lots of information. In addition, there are friends who are happy to share what they know with you or to go along with you.

If you know about something, you could share it with others. Look into Mountain Mamas if you want to learn an outdoor skill you don’t have already.

A good coach shortens your learning curve, helps you avoid unnecessary mistakes, and sees blind spots you can’t.

Whether your goal is physical, emotional, professional, or spiritual, you don’t need to do it alone.

How could a coach teach you more quickly what you need to know? How could a coach help you stay motivated when things got hard? Who do you know that has done it before?

5. Motivation Must Come From Inside

Crisis often is the catalyst for change. A car accident, health diagnosis, children’s choices, financial setback, business failure, divorce, jealousy; all of these things can either destroy you or motivate you to change.

Some of these circumstances can’t be controlled, but you always have control over how you respond.

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.”
Viktor Frankl

If you are waiting for something external to motivate you to change, it will eventually happen. I’d rather motivate myself to grow and develop before I feel forced to.

Consider what your life might look like next year if you continue doing the same things you are doing now. And then picture what your life might look like if you changed one thing.

Got up 30 min earlier to meditate/pray, exercise

Read instead of watch TV

Reach out to a friend once a week

Spent 30 min a day writing

Spent 30 min a day working on a website

Took a class

Practiced thinking kind thoughts

Impossible goals are fueled by internal clarity, not hype.

What will your life look like in a year if you change nothing? What do you want to change or start doing for you? How will you respond to the crises in your life?

6. Build a Team That’s Stronger Than You

No serious goal is achieved alone.

Jenn intentionally surrounds herself with people who are:

Stronger
More experienced
More knowledgeable
Better in specific skills

Your job isn’t to be the best at everything. It’s to assemble people who complement your weaknesses.

You may have 20% of an idea, strength, ability. Rely on your team to put in the 80% you are lacking and you can all be successful. Jenn’s small body size limits the amount of gear she is able to pack in, so she makes sure to have some big, strong teammates to balance what she is unable to do.

Leadership means knowing when to rely on others.

What support might you need to accomplish your goal? What unique talents do you have to support the group? What skills are you lacking? Where can you go for more help?

7. Know When to Pivot—and When Not to Quit

This may be the most nuanced lesson of all.

Jenn has walked away from more than one mountain, as many mountain climbers have. Sometimes a goal needs to be paused or abandoned—because of sickness, tragedy, weather, or safety. Quitting in these moments isn’t failure; it’s wisdom.

Other times, persistence is required:

When plans fall apart
When gear is lost
When communication is difficult
When the path forward feels uncomfortable

The key is discernment. And just because things fall apart and you are unable to reach your goal doesn’t mean the goal is unattainable. Learn from mistakes. Try again.

Know what deserves grit—and what deserves grace.

Is what you’re doing working? Could you change something to be successful? Has this become dangerous to yourself or someone else? What do you have control over?

Final Thought: What Are You Normalizing?

We all take risks every day. Are you allowing your environment to control you or are you controlling your world by normalizing the things that scare you? Think about this question: