EP 288: Rethinking Your Business Amidst Change With Second Breaks Founder Lou Blaser

In This Episode:

  • Why I chose “embrace uncertainty” as one of my commitments for 2020 and how it’s served in this wild year
  • How Charlie Gilkey recommends finding the most courageous next step
  • What led Second Breaks founder Lou Blaser to rethink her business model—and return to a years-old vision for her work in the process
  • What 2 questions she used to find new ways of creating value
  • How she used existing assets in her business to start building toward her new vision

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The tweet that’s pinned to the top of my profile lists my 3 commitments for this year.

Those commitments are my guiding principles, the things I’m actively trying to cultivate more of in my life, the ideas that guide the decisions I made.

My three commitments for 2020 are: Question normal. Expect success. And embrace uncertainty.

Now, most people I know have had to recalculate their goals for 2020. But these commitments? Well, they’re more relevant than ever.

In fact, I’ve had a few people @ me on Twitter and ask if I’m psychic!

While each of my commitments for 2020 have been a huge help for navigating this wild year, it’s that last one–Embrace Uncertainty–that’s really asked me to grow.

Uncertainty seems to be the theme of 2020.

With everything that’s happened so far this year and no real confidence in what might be coming, we’ve all had to recalculate.

Some business owners I know have had to completely rework their business models. Others have taken huge in-person gathering online. Others are discovering they have skills that are incredibly useful in the pandemic economy. And still others still aren’t sure what they’ll do next to bring in some revenue.

As I’ve worked with business owners on making decisions and reworking plans, there’s one thing I keep coming back to, though. While 2020 might have presented us with a unique batch of unpredictable circumstances, uncertainty is not a new condition of entrepreneurship.

Uncertainty is baked into the operating system of how we function every day as business owners…

…whether we like it or not… and whether we like to admit it or not.

When I chose embracing uncertainty as one of my commitments for this year, I didn’t have a pandemic in mind.I wasn’t gearing up for a historic upheaval in the labor market. I didn’t predict the long overdue tectonic shift in public opinion about systemic racism and police brutality.

I chose to commit to embracing uncertainty because I wanted to take more courageous action. I wanted to see what would happen for me and for my business if I stopped trying to predict the right thing to do and started leaning into my full potential and my full vision.

And while you might think I’m a natural risk taker, I can assure you I am not.

This idea wasn’t really mine at all. It was a very important lesson I learned from my friend Charlie Gilkey during an interview for this very podcast.

Before we get into this week’s interview with Lou Blaser, I want to share a snippet from this interview to tee up all of the conversations we’re having this month around embracing uncertainty. Charlie’s answer to my question about the difference between taking the smart next step or the courageous next step sent my mind whirling:

“The first question is what’s the smart next step. And then what’s the most courageous next step. The reality is your most courageous next step is almost always the smartest next step, but we have to get to that place and let go of that certainty, that fear of failure, that fear of ostracism.”

He went on to explain that the courageous next step doesn’t have to mean the biggest next step. It can be something small:

“Choose the options where comfort would dictate one way of going and growth would dictate another. Choose the option for growth. If you choose those in those email exchanges, if you choose them in the conversations with clients and customers, if you choose them in conversation with teammates or partners, it can make a world of difference.”

That’s what I committed for this year.

And while I might not have made every courageous choice I could have in the face of uncertainty, I haven’t backed away from uncertainty or tough decisions. I’ve sent the hard emails. I’ve faced the criticism. I’ve shown up to lead.

And it’s served me well.

But my story is just one story among many. We are all facing uncertainty–as we do every day. So I wanted to talk with business owners who have their own stories about embracing uncertainty this month and the first person I thought of was Lou Blaser, the founder & host of Second Breaks.

I’ve watched Lou embrace uncertainty over and over again throughout the years. I’ve watched her step outside her comfort zone and I’ve watched her take courageous action.

Earlier this year, she announced that she’d made the decision to upend her business, then a career coaching company for late Boomers and Gen Xers, and move back to the Philippines to help out with her aging m. And while she could have tried to continue with her business as is–she made the bold move to use the change as a way to rethink everything.

That’s where this conversation starts–and throughout, Lou and I talk about how her business has evolved, the questions she asked herself to create the new plan, how she could use her existing assets in new ways, and how she started experimenting with her new ideas.

Now, let’s find out what works for Lou Blaser!

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EP 299: How To Design Your Own Sales System

EP 299: How To Design Your Own Sales System

This week, I’ve got 4 more stories to share with you from small business owners who have intentionally done things their own way when it comes to sales and selling. They’ve found what truly works for them–even if it bucks the prevailing wisdom or would make a bro marketing expert role his or her eyes.

These stories come from business coach Ashley Gartland, marketing expert Amy Lippmann, designer Mel Richards, and work reinvention coach Lydia Lee.

Listen for how they incorporated these same considerations into finding their own unique sales systems. They designed their systems with personal values, strong relationships, reduced anxiety, and agency in mind.

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

EP 298: Creating A Less Harmful Sales System with Wanderwell Founder Kate Strathmann

This show is called What Works for a reason.

Sometimes it’s a declaration: this is what worked for this small business. And often, it’s a question, “What works?”

Today’s episode is very much a question, many questions, really:

What works when it comes to selling when you want to avoid manipulative or exploitative practices?

What works when your values conflict with many of the best practices of selling online but you still want people to buy your stuff?

What works when it comes to sales in a business that is actively anti-racist and anti-capitalist?

And even more bluntly: Can you even sell things without causing harm or perpetuating harmful systems?

My friend Kate Strathmann is the founder of Wanderwell, a bookkeeping and consulting firm that grows thriving businesses while investigating new models for being in business.

Recently, Kate took a bit of a detour from how she’s used to building her business, which is 90% referral based and fueled by deep relationship- and community-building. She decided to offer a small group program called the Equitable Business Incubator as a way of exploring anti-capitalist business practices and how they apply to the small businesses we’re building.

To fill the program, Kate need to sell differently.

Which led her to asking the question: Can you even sell things as a anti-capitalist?

While that might not be your specific question, I have a feeling that you too have wondering how you can effectively sell your offers without causing harm, perpetuating harmful systems, or damaging relationships. And that’s why I knew Kate and I needed to explore this topic on the show.

This is a conversation about what a kinder, less harmful sales process could look like—and it probably contains more questions than answers. But I’m confident those questions can help you find the answers that are right for you and the sales system that you want to build to make your business stronger.

We start out by defining what we’re really talking about when we talk about capitalism and anti-capitalism. Then, Kate shares how the Equitable Business Incubator came to be and how she ended up selling it. And then we dig into what makes many of the sales formulas and best practices being taught today problematic—and how to think differently to create your own alternative practices.

Now, let’s take a look at what works for creating less harmful sales systems!

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

EP 297: Selling A New Program With Proof To Product Founder Katie Hunt

Today’s guest is Katie Hunt—who is a member of the former group and serves the latter group.

Katie is the founder of Proof To Product, which helps creative entrepreneurs run and grow thriving product-based businesses. She works with designers, illustrators, and artists to help them develop in-demand product lines and get them sold in stores all over the world.

Not long after the pandemic threw her business and the industry she serves for a major loop, Katie and her team launched Proof To Product Labs to provide a completely digital, ongoing support opportunity for business owners when they needed it most.

And that launch was a smash.

Katie and I get into all of the nuts and bolts of how she adjusted the offer to meet the moment and how she warmed up her audience before the campaign, as well as the exact mix of emails, podcast ads, and social media content she used to sell the offer when it went live. We also talk about how she sees the sales system evolving in the future and how the offer has been received now that people are using it!

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