A $2,500+ Investment and a Career Break Plot Twist I Didn't See Coming

Is this the end of my career break? I’m back from two creator events in Boise with my brain absolutely BUZZING, and a question I'd been avoiding for almost a year staring me right in the face.

This episode is me finally telling you what I've been working on and what it means for what's next.

In This Episode:

• Why I almost skipped the $2,500+ investment that ended up changing everything
• The pattern I kept noticing in Boise that I couldn't ignore 
• The skill I buried in the attic after my layoff, and why I'm pulling it back out
• An honest update on the money I've made during this career break

Resources & Links:

Episode 6: Money or Freedom? The Two 6-Figure Offers That Almost ENDED My Career Break (published February 10th)

Episode 9: From 6-Figures to $1,127 in Gig Work: 3 Humbling Months of Being "Busy" (published March 3rd)

Let's Connect:

Follow me on Instagram: @alisonkinsey or send me an email: alison@alisonkinsey.com. 

Connect with Alison on LinkedIn.

I also help entrepreneurs and thought leaders launch and grow their podcasts through my boutique podcast editing agency, Podcasting for Creatives. 

Transcript

SPEAKER_00 0:00

It really took going to this conference to realize that my highest, most valuable skill is the one that I've been running away from. This could be a thing. Like, do I go back to sales? Hello. I have to admit, when I first sat down to record this episode, I could not even get the words out, which is so rare for me. Usually I'm just on fire, blabbing away. I did a few retakes and it still wasn't working. I kept stumbling in the same spot. And it was the spot where I was going to tell you some pretty big news. I had an epiphany about what I'm going to do next. And it basically signifies the end of my career break and the start of an entirely new chapter. So I want to take you through what actually changed in the last three weeks because a lot has been going on behind the scenes. First, I invested over $2,500 this month to go to two different creator events. And at this stage in my career break, $2,500 is nothing to sneeze at. To me, it feels like a serious amount of money. But I was feeling this pull to connect and be in rooms with people smarter than me. And to break it down for you, one of the events was a mastermind style format. So Jay Klaus, one of my favorite creators and podcasters, he hosted this event with 43 creators in the room. And the other was Kitts Craft and Commerce Conference, which has about 400 to 500 people coming down to Boise, Idaho every year. Not the easiest place to get to from Boston, but I was like, I'm going. And my family, like as the event was coming up, you know, I was starting to get my clothes together and my outfits. They kept asking me, like, what are your goals? What do you want to get out of going? And I told them, I just want to meet incredible people and get inspired. That's it. But somehow I walked out of that event accidentally discovering my next career pivot. And it still feels so surreal, even to me, that I haven't updated my LinkedIn profile. I haven't even told a lot of people. I've just been kind of sitting with it privately because I'm like, oh my gosh, this is so wild, at least to me. And the crazy thing is, I almost didn't go to either of these conferences. I was hemming and hawing a ton about the entire conference investment. Like, is it actually worth spending $800 practically to stay in a hotel for the week? Is it worth spending this much money on a ticket? And I brought it up in therapy. And my therapist was like, Will you come away from these events feeling energized or depleted? It's such a simple and direct question. And right away I knew my answer. I booked my flights later that night and grabbed my tickets right before it sold out. There's this saying that you have to spend money to make money. And I kind of roll my eyes at it because it's such a cliche thing. But it really took going to this conference to realize that my highest, most valuable skill is the one that I've been running away from, which is my sales background. When I got laid off in August, I pretty much took my sales hat off, buried it in the very back of the attic, and shut the door. Like I was done, dusted, moving on, leaving that part of my career behind. But it totally and unexpectedly came out of hiding at these two events. People I met were telling me about their own sales processes or what their average conversion rates were, or what I kept hearing over and over. They didn't really love taking their own sales calls. It kind of baffled me at first because I walked in. I mean, I was planning out my whole introduction, like, how am I going to share what I'm doing with people? And I gave them my whole story. I told them about podcasting for creatives. I told them about my creator journey and the launch of this podcast. But of course, I also shared that I sold to top creators for almost six years. And people just kept looping back to sales. And I didn't take it seriously at first. I was like, eh, like that's cool. People are curious about this. But it was when someone approached me and told me to put my number in their phone mid-conversation, that it really hit me that this could be a thing. Like, do I go back to sales? And if you've been listening to the podcast for a while, you know, if you had asked me that question, especially when the wound of my layoff felt really fresh, the answer was a full-bodied no. Like I actually felt it in my body. I felt the resistance and the tension. The timing just wasn't right. And it was even to the point where some opportunities did come knocking several months ago and I turned them down. And I did a whole episode on that decision spiral that I'll link in the show notes. But flash forward, and I feel like I'm now in a completely different place. I'm now almost 11 months into a career break. And I have to admit it, to be honest, I'm having my own reality check moment that sustainably I can't do this forever. I can't just be on a career break living like a retiree and doing whatever I want. I mean, in my own glamorous dream world, I would totally continue on this career break fellowship reinvention journey and just take a whole other year off. But I know it's not realistic when I think financially and for what my goals are with that. And as far as my personal contributions in the last 11 months, so not counting podcasting for creatives, I have brought in $1,127. That's it. And I made that just dabbling with different forms of gig work. So I did mystery shopping, I supported as a wedding venue coordinator, and I did tons of market research projects and calls. And our podcast editing business is steady. It's going super well. I'm always grateful for it, but it can't be our only income stream. And that's really the moment of realization that I've had recently. So I flew home from the events with my mind quite frankly buzzing, like total overload with all of this new information to process. And it started to feel like, whoa, maybe the timing could be right to go back to sales. And as I'm talking myself through this, you know, I'm recognizing it is one thing that I'm definitely good at. Maybe there's a path where I could do this part-time and fractionally so that I can still create a really fun lifestyle around this work rather than letting the work take over my life. It's so funny. I feel like sales has such a reputation. You say the word sales, people have their own ideas of what that is. They think of like the shark car salesman, or they think about the grifter kind of coaches that are just like taking your money and it's not even worth it, and they're preying on people that can't afford it. I know there's just so many thoughts that we all have around sales. There are many parts of the process that I genuinely like. So I was sitting with that too. Like, I love crafting a damn good follow-up email that's super personalized to that person. I believe I build trust quickly with people. It feels like one of my superpowers. So when they're on a call with me, they feel like they're being taken through a process that feels genuine and authentic. I feel like sales doesn't have to be icky or slimy. Like, especially if you're the one doing the sales, I understand that maybe it's not your favorite thing to do. All of the sales that I've done in the past were super consultative. So it felt like just a normal conversation. And usually the person actually wanted what I was selling. So, to be fair, I have not done outbound sales. I haven't done a lot of that where you're just kind of reaching out cold. But if it's someone that's coming in inbound that fills out a form or they book a call on your calendar, one could think that, hey, they might actually want what you have. And if they signed a contract, it always felt like a win-win. They were excited. I got to ring the bell. I felt the little dopamine hit. I could like check things off on my whiteboard. But I also got to stand on the sidelines and watch that person launch their new thing or have this really successful moment in their business. So, all of that aside, not even two weeks after coming home from Idaho, I signed my first fractional sales contract. This is the first time I'm like really saying this out loud. It is happening, you guys. And I can't believe how fast it happened. And I feel like leaving that series of events, my spark and ambition for work, I just felt it coming back. Even my hunger to actually create again, that feeling of purpose that I talked so much about in the first few episodes of this podcast. It's like I'm starting to feel that again. So, where does this ultimately leave the podcast? There's a reason that I named this show Real Time Creator. Before launching this podcast, I thought I was going to choose a name that had to do with career breaks. Like I thought career break would be in the title somewhere. Ultimately, I didn't do that. So it feels like I have this name that can kind of carry through into this next part of my chapter. And I feel like the story is far from over. In fact, I think it's just beginning because there's even more to share that I have not shared yet, kind of waiting for the right moment on that. But here I am launching a new fractional business. I'm essentially building out a portfolio career between this and podcasting for creatives. There's a lot of people thinking about going fractional as opposed to going back into full-time work. So if you'd like to chit chat more about any of this or my transition into fractional sales, just send me a DM on Instagram at AllisonKinsey. And as always, thank you for listening and for cheering me on. I'll see you next time. Bye.