112: My 3 Biggest Business Regrets

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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.

Before we jump into this episode, I want to give a big thank you to a new review that came in from Money Smart mom in Canada. She said Invaluable guidance As an author and speaker, I get so much valuable guidance, tips and ideas from Jenny's podcast. The episodes cover everything you might be wondering about as a heart based business with a delightfully tiny team. Plus, Jenny always has a smile in her voice. Can't recommend enough. Thank you so much for this beautiful review that means the world to me. It makes my day and I really want to say thank you Money Smart mom in Canada. Thank you to all of you who are here listening. If you want to support the show, leave a review. Tell me what has been one of your biggest insights or AHAs, or even better, a new practice that you've put in place to free your time as a result of listening. You can go to lovethepodcast.com freetime that's lovethepodcast.com freetime and if you enjoyed this episode, please do share it with a friend. The best way to do that is by grabbing a pod link. Go to Pod Link freetime. That's Pod Link freetime that allows the person you send it to to open up the episode in whatever podcast player they prefer. It's my favorite tool yet for sending episodes to friends. With that, let's dive in.

In his book the Power of How Looking Backward Moves Us Forward, Daniel Pink describes why. As tough as it is to stomach, sometimes regret can be a helpful catalyst, he says. Regret is better understood less as a thing and more as a process, one that doesn't just make us human, it makes us better, he says, by making us feel worse. Today we regret helps us do better tomorrow. Understanding its effects hones our decisions, boosts our performance, and bestows a deeper sense of meaning. Our topic for today's solo riff are my three biggest business regrets. Or you could call them strategic errors. In 11 plus years of running my own shop. What's a little funny is that even as I say the title of today's episode, these are the biggest business regrets or, or strategic errors that I'm aware of. But I'm also wondering as I record this, what are all the blind spots, the things that maybe I'm not seeing, that I don't even know to regret because they're under the surface of my awareness? What I've been doing is reflecting on this question. I don't even know how this prompt came to me, but I thought to myself, what are three things out of so many out of probably 300? What are the three big ones, the big strategic errors that I think, looking backward, I could have done better, I could have done differently to run a more consistent, profitable, and of course, all the while joyful business? In his book, Pink talks about three different types of regrets. Interestingly, mine sort of map to this pretty well. I came up with my list of three before I reread this takeaway from his book. But you might find these interesting. Foundation regrets sound like if only I'd done the work, Boldness regrets sound like if only I'd taken that risk, and moral regrets sound like if only I had done the right thing. All right, so let's get into these three biggest regrets. And they pretty much map to Pink's categories, even if not precisely first and foremost on a foundational regret. In my business, one regret looking back is not having one flagship course, and particularly one that would be evergreen. I love learning and development. That's what I did when I worked at Google. It's what I played as a kid. I used to make my brother play school and I would create these worksheets for him and his friends to fill out. I've always enjoyed teaching and I think that this strength became a weakness in the sense that I was always creating new courses and I didn't ever go all in on just one. When I first Left Google In 2011, my very first course was called Make Shit Happen and I sold it out in 24 hours. I did all the online marketer techniques that you're supposed to do. The second time I ran, it had a little harder of a time filling spots, but people were saying such great things about their experience. But by the third and fourth times I thought about launching it, I kind of moved on from the material. Even though I had written this almost hundred page ebook, it was a 10 week course. I did live calls. We had so much fun together. If anything, that became the foundation for my private community that has morphed over time from being called Brilliance Barter to Momentum to Pivot Insider and now it's bff. That course then led me to create something called Build you'd business in 2012. I had so much fun. People said they learned more from that course that was I think $75 or 175 at the time. They learned more than some $2,000 courses they had taken. It was so much fun. But I felt a little bit like a fraud teaching a course called Build you'd Business as I was still learning how to build my own. So sure enough, when it came time to relaunch that I just got cold feet. I created courses like Delegation, Ninja Email, Exhale, Heart of Podcasting, Heart of Book Publishing, Pivot to Profit, Free Up, Founder Time. You could see that all of these courses have similar shared themes. They're always bolstered by my love of systems, process, efficiency tools, practical tips and inspiration, and that live experience of a cohort coming together. But as I said, I never went all in on just one. So that meant that I was always creating new landing pages, new marketing materials, new launch process, new email sequences. It meant that I was never really gaining traction with any one course because I kept going to the next shiny object or the next subject matter that I was interested in. Now, you could say that it's good to pilot lots of different courses and material to see what's going to stick. What am I going to enjoy most? But I think if I had known 11 years ago, if I had said to myself, jenny, what is one topic that you could teach on timelessly that you'll never get sick of, that you could improve year over year, but that you might not get sick of if you were to market it for the next five years in a row? What would it look like to have stuck with one big flagship so that instead of always creating a again, new launch communications, new sales pages, new testing, new checkout process, and all of that, not to mention creating the courses themselves, what would it have looked like if I could have reduced some of that zero to one energy and put it into improving something over time, not just improving the course, the outcomes for students, but the process of marketing it and creating a regular cadence in my business and getting better and better at the process of of enrolling people in this course. I did see fellow entrepreneurs doing this. I saw people who very successfully marketed a flagship course over years and years and years. And I honestly watched that with admiration. Like kudos to them that they don't get sick of this material, that they want to teach the same thing, that they even landed on the one thing that they were excited to teach year over year and launch year over year. That's regret number one. No flagship, and particularly again, an evergreen flagship. Something that the material would not get stale. I think I could have been more intentional in the early days of creating one thing that I hang my hat on.

We'll be right back just after this.

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The second regret that I have in my business is a boldness regret. This falls under the boldness category plus or minus, and that is that when I was starting the Pivot podcast in 2015 and I launched the book Pivot in 2016 almost a year later, I got all this podcast momentum at a very critical time. And it was early on, podcasts were still not quite as ubiquitous as they are today. It wasn't that every big celebrity and every major media brand had a podcast, yet they didn't. I'm not saying I was anywhere near first to the game. I have friends who've been doing it since 2005. 6. I was still a decade late, if you will. But when Pivot the book came out, I did this big podcast tour. It was backed by portfolio and help with the publicist lining up shows with all these different people. Even James Altucher had me on his podcast, which was pretty massive at the time I did a guest hosting of his podcast and he came on mine. And then I stopped. I was so tired from the book launch and I hadn't quite planned quite enough episodes in the can. Three months of consistent episodes that were gonna take me from September, when the book came out, September 2016, all the way through, let's say, the end of that year. Better still, I would have planned into January. I kind of lost steam a little bit, and I wasn't publishing episodes as consistently as I could have during that window. And I regret this because this is kind of a boldness failure. I failed to double down on something that I was enjoying. I failed to get the proper team and infrastructure support. I failed to plan enough so that I could really take advantage of having so much visibility, in a way, the most visibility that I was going to have for the next five years because of doing the Pivot podcast tour, where I don't even know how many interviews I did. 40, 50, 60, who even knows? But I was everywhere on all these other podcasts. And I could have done so much better of not just planning on how to be consistent on my own show, but how to blow it out of the water, how to say, oh, I'm gonna have all these people coming and checking out my show. How do I make it amazing heading into the fall and post book launch, how do I make it the best show that I possibly can? And it's hard during a book launch to know exactly what to do, what to focus on. I would also say that at that time, I wasn't 100% clear that podcasting was gonna be this main love of my business. I had started it as this little side project that would go with the book launch. And I certainly didn't know where the podcasting landscape overall was gonna go. I just knew that I loved it. Another thing that I didn't do as it relates to boldness and going all in with the podcast in that crucial window of 2016 was, was mention it more at the end of interviews. I was promoting the book and always the host would ask at the end, where can we find you? And I would give my website and the Pivot toolkit and the book. If I were being a little more strategic, I probably would have plugged the podcast a little bit more than I did. Because now it's become clear that podcasting is really tricky. I never wanna say hard. I don't like to plant those exact seeds in my own mind or others, but it's quite tricky to grow a show. It's not obvious. There's not good metrics in terms of any one source of trut of subscriber count or download. There's a lot of attrition because there's more and more shows getting added into the mix all the time. So there's more competition. It's tricky and yet I love it. What can I say? The third biggest regret or strategic error in the last 11 years. And I think this does go to not just a blind spot, but a personal weakness of mine in terms of lack of interest is not creating any predictable growth engine specifically as it might relate to ad spend. Now you could kind of lump this into the moral regret category if only I'd done the right thing. I do now only because I have a moral obligation in a sense to support my family and to support myself. I never want to be a burden on others. I always want to be able to support myself and I want my business to be able to ride out really tough times. None of us could have predicted a pandemic, but still feeling the effects of it. Specifically in the speaking business. That for a long time was the biggest cash flow that I had. It was so nice, even if I just got one gig for 10 or 15k once a month. That really kept the lights on and it provided a nice sense of buffer as I was trying to get anything else off the ground. Now I also have some corporate licensing clients. Those tend to renew once a year, so it's always nerve wracking to get to that time of year because I don't ever want to count those chickens before they've hatched, but they were certainly delightful and helpful when they do so with speaking and events. So down the last few years it has been challenging to figure out the best places to put my energy and the best ways to create predictable growth. This is again, a strength as weakness. I've always leaned into serendipity and flow and marketing with magic and ease and joy and fun and all those things. No regrets about that. But that means that what I haven't done is been so committed to growth hacking and AB testing and spending any excess cash flow on ad experiments to figure out if I put in a proverbial dollar here, where can I get a proverbial two in return? And I say that because it's not that easy, of course, to just put in a dollar get two back. I recently ran some podcast ads on Overcast and I spent maybe $1,000 to advertise in the business category and it ended up that based on the number of new subscribers, the cost per acquisition or CPA was $20. That's a lot. Unless every single new subscriber joins BFF or signs up for the Free time dashboard or the free Up Founder Time course. You know, there are ways to engage, but it's not always going to be a direct line, nor does it need to be. But $20 per subscriber, that's a lot. I'm sure I could get that number lower, but I have not committed myself in a diligent or consistent way to building a growth engine, a growth machine where I can really study what inputs are going to lead to what outputs and then be able to ramp that up. What's more, I started my career managing Google AdWords accounts when I worked at the startup as I was finishing school at ucla, so I knew how to run ads. I was learning AdWords software when it was brand new. Then I pivoted over to Google, teaching customer service rep how to support the AdWords product. Why didn't any lights go off in my brain to say, jenny, apply this process to your own blog at that time. When I first started blogging, 2005, I set up my website and the blog started in 07. I was networking and that's something I think I did well during that time, networking with other bloggers. But we all kind of just thought it was this hobby, this fun thing. And yes, it was fun to get on lists and top millennial blogs, things like that. I would have never thought to spend my own money, especially kind of when I was in those entry level days, I would have never thought to spend it on Google Ads. Even though it was what I was teaching at work, it was what I was learning at work. I worked within Google. There was so much of an advantage that I had that if I had started advertising things like my blog, my books, my podcasts 10 years ago, I don't even know where I would be today. It never clicked. It never clicked. Those dots never connected in my mind to this day, I have never run Google Ads. I am completely stubborn about not advertising on a big social media platform that I just don't resonate with. I'm stubborn and this is something that I don't know. I'm not saying that money and growth is the end all be all. I don't think any of you would be here if that was my vibe because I'm so focused on the big picture of how it feels to run the business and how much time we have as one of the key measures of success, not just the money. In the bank or the growth chart up and to the right. But that's a regret in a way that if there's going to be a big recession or if there are really fallow times, it's good to know. Not just that, the big ideas. I've always been focused on creating ideas that could be resilient during an up or a down cycle in the markets, but also having certain predictable growth engines so I would know what to turn on when, if I could. That said, even those growth engines are unpredictable. In the early days of blogging, I had friends who would do affiliate sites and they were big on SEO optimizing, and one change from Google and boom, their whole strategy would be kaput and they'd have to rethink things. So I know there's no magic bullet to this stuff, but I think this is one of my bigger regrets is saying, all right, Jenny, you're 11 years in. Are you running a business or do you have just a fancy hobby? And that's probably one of my bigger business gremlins is the gremlin that just says, well, if you don't even have predictable growth engine, it's a hobby, not a business. Although I do look at companies like Uber and Pinterest. There are some massive companies that are not profitable to this day. Then I remember to cut myself a little slack to close out for today. You hereby have permission to drop the guilt over the biggest regrets you have in your business. It's okay, we all make them. And as Daniel Pink says, this is how we learn. This is how we grow. This is how we improve. It would be impossible to be running a business with all the thousands of decisions you have to make large and small without leaving some regrets along the way. You have permission to forgive yourself and you have permission to try again. Now. I would love to hear from you because I feel like I'm standing out there alone on a branch right now just sharing what I could have done better. And I'm so curious, what are some of your biggest business regrets? What are your regrets in terms of foundation work that you could have done earlier on in terms of boldness, risks that you coulda, woulda, shoulda taken, or even moral regrets? Just doing the right thing by you, by your family, by your energy, by your health. Be so curious what you have to share on this topic. You can always leave me a voice memo@itsfreetime.com Ask or you can record a voice memo on your phone and send it as an attachment to hitime.com thank you so much for being here. Listening everybody. I really appreciate it. Have a beautiful rest of your day.

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