Learning To Fail When You’ve Always Been Successful

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I’ll admit. In my career, I’ve generally been successful the first time I’ve tried something. Sometimes that success has come naturally. Other times I’ve had to work like crazy. But I was nearly always able to get it mostly right the first time around.

Not anymore.

Entrepreneurship feels like a daily wake-up call, a continuous journey outside my comfort zone. In the most humbling, amazing, frustrating, growing way possible.

There are moments when I’m riding high, overflowing with gratitude for the work I get to do.

And there are times when I feel like nothing works and I have no idea why. When I believe I’m putting something high-value into the universe and no one responds. Or they like it – but won’t actually pay for it.

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This has been the last few weeks for me. This fall I piloted a group coaching program for women to get control of doubt and imposter syndrome and own their strengths so they can move forward in their career with confidence. It was AWESOME. I loved every second of working on it and the people in the program loved it as well.

This is it! I thought. I’ve found my signature program. I even had another person sign up for the next round of the program just as I was finishing the first.

It turns out I was wrong. After launching multiple marketing strategies, I’ve realized that this particular program isn’t connecting with people.

In short, I’ve failed.

It’s not fun.

But I’m realizing it’s fine. Healthy. Maybe even a good thing.

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Ten years ago I sat in the Mexico City airport with a participant from one of the leadership development programs I coordinated at Cargill. While we waited for our flight back to Minneapolis, she shared that another participant had asked her, “How do you know how far you can go if you’ve never failed?”

I realized in that moment that I had never failed either (at least professionally!). And in the ensuing ten years I spent in corporate after that conversation, I never really failed. I wasn’t perfect, but my good was always good enough.

So I’ve never really known how far I can go.

Now is my opportunity. To embrace the highest of the highs and the lowest of the lows and learn from them both. To LISTEN. To create my business from a combination of what comes from that listening as well as my personal knowledge, values, and purpose. To dream bigger than I ever have before. And to EXPECT failure along the way.

It won’t be easy. It will be often be uncomfortable. There will be tears. And also joy.

And it will be worth it.

Are you hiding in busy work?

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I make a to-do list everyday. Until a few months ago it was just one long list of everything I needed to get done that day, whether it was as simple as a quick email or as complex as creating a marketing plan.

I got most of the things done everyday and I felt pretty good about it.

And then I realized the 1 or 2 things that weren’t getting done each day were the things that would really propel my business forward. 

There are so many reasons to skip the big work – it often takes more time to do the bigger work, it needs more energy and headspace, demands higher creativity.

But there’s another reason. 

The big work was totally outside my comfort zone.

The big work involved putting myself out there, asking for what I want, and potentially facing rejection. It also brought up all sorts of inner critic imposter thoughts like “You’re being too salesy”. 

I was hiding in my little work. The busy work that makes me feel productive, but doesn’t actually move me in the direction of my big dreams and goals. 

And I didn’t even realize I was hiding. 

Now I make two to-do lists each day – one for big work and one for little work. This tiny shift has made a huge difference. When the big work is laid out so clearly it is impossible to hide. 

I want you to take an honest assessment. Are you hiding from your big work? Are you making yourself busy so that you can feel productive while safely tucked away in your comfort zone? 

Commit to doing your big work in 2019. Categorize your to-do list like I did or write down just one thing each day that will move your forward towards your big goals. 

Stop hiding from your dreams. 


P.S. If you want to stop hiding and start moving in the direction of your dreams, register for my live webinar this Friday, January 18 at noon central: The Five Steps To Master Doubt and Reclaim Your Confidence. Click here to register on Zoom. Just enter your name and email and you’ll get a confirmation with the link.

How to say no to things you really want to do

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There are articles and blog posts all the time about saying no to the things you don’t actually want to do.

That’s never been a big issue for me.

My problem is saying no to the things that I really, legitimately WANT to do. Because I want to do everything! I want to be involved. I love to learn. I enjoy being out in the world doing things. I’m always the first one to say to a new adventure.

But I can’t do it all.

So I have to say no – even to things I really want to do.

This realization came to me a few years ago when I said yes to a fantastic project – leading mentoring for the Cargill Global Scholars Program. I was tasked with creating the structure and support for over 50 university students from across the globe that would be paired with Cargill employees as mentors. Amazing, right? I thought so too.

So I said yes without even pausing to think.

I said yes in the same month that I returned from my expat assignment in Australia and started a new job at Cargill that would require a huge amount of learning. I said yes when I was in the midst of moving back into my condo. I said yes when I was rebuilding friendships that I had been absent from for a year and a half.

I spent at least four hours a week on this project for the next year. Parts of it were amazing. It was completely aligned to my values. I loved seeing the connections made between students and their mentors. I felt awesome when the students came from Brazil, China, Russia, India, and the US to Minnesota for a leadership seminar and I got to meet them and hear what they were learning from the program.

But I still should have said no.

What I realized in the midst of all this is that when you say yes to something, you’re always saying no to something else.

The challenge is that the choices aren’t usually stacked next to each, so it doesn’t look like you’re choosing between things. But you are.

When I said yes to this amazing project, I said no to leaving the office at a reasonable hour each day. I said no evenings and weekends free from work. I said no to really enjoying all my social activities because, even though I went out with my friends, my energy wasn’t always there to fully engage.

In short, I was overwhelmed, overworked, and exhausted.

So I started to pause before I said yes to new offers. I told people that I needed to think about it and would get back to them instead of responding with a yes or no in the moment. I asked myself “What am I saying no to if I say yes to this?”

I’ll admit, I still want to be involved in everything. I consistently have to remind myself that I can’t do it all – that I have to say no even when I want to say yes. It’s a practice.

But it’s a practice with massive rewards. I have more time and energy for my true yeses. I can dig in deep with them and contribute more of myself. I also get more sleep and feel less stress and overwhelm.

What do you want to say no to this week?

 

Heather Whelpley is a speaker and coach that works with women to master doubt, own their brilliance, and step into the career and life they desire. Click here to learn more.