Be Bored and Rich: What Entrepreneurs Get Wrong About Passion, Purpose, and Resentment

The Gap vs. The Fix: The Only Feedback Framework You Need

Most leaders think they're choosing between two options when it comes to feedback: be vague or just redo it yourself. Adrienne and Emily have a third take. In this Dear Bossy episode, Adrienne and Emily tackle a listener question about how to give feedback that actually sticks. They get into the difference between lazy and specific feedback, what it really means to delegate well, and why "make it stronger" does more harm than good. What they cover: * Why "make it stronger" and "make it better" are lazy feedback, not vague feedback, and what the difference actually means for your team * The false choice between being too vague or rewriting everything yourself, and the third option most leaders miss * How to turn subjective feedback into an objective standard your team can actually measure against * The gap vs. the fix: why naming the gap gives people ownership, and handing them the fix takes it away * What it looks like to give feedback on creative or preference-based work, and why rewriting with a walkthrough can actually be the fastest path to improvement * How standards change over time and why updating your team is not a one-time event * Emily's real example of getting "add more energy" as feedback and why it landed flat without context * The ego trap: unconsciously setting people up to fail so you can stay the only one who can do it right Submit your own Dear Bossy question: sortabossypodcast.com [http://sortabossypodcast.com] ⏱️ Time Chapters 00:01 Happy Tuesday and rainbow loom necklaces 04:05 Taylor-formations card of the week 06:21 The listener question 07:10 Emily's take: rewriting is not always the lazy option 09:47 The false choice and the third path 13:05 The ego trap in delegation 17:40 When standards change: the leader's responsibility to update the team 22:05 Emily's personal feedback example and user manuals 25:58 Choosing your hard: paying credit vs. paying cash 27:49 Wrap up

This One's for the Girls

Some decisions don't feel like decisions. They feel more like a slow accumulation of clarity that finally gets too heavy to ignore. Adrienne has been moving toward something for years. This is the episode where she names it out loud. Adrienne and Emily sit down for a get-to-know-the-boss conversation that turns into much more than business. They unpack what it actually looks like to trust your gut over a long period of time, why Adrienne's work is now specifically for women, and what it costs to finally stop trying to be something for everyone. What they cover: * Why Adrienne declared her work is for women only, and the personal losses and decisions over the past two and a half years that led her there * The male anchors that shaped her life (her dad, her ex-husband, her business partnership) and what shifted when each one ended * How she ended up in a business partnership with Mike and why her original work was always the foundation of it * The four exits framework for female founders: sell, scale, step away, or succession plan * Why trying to be for everyone made her content confusing and what it took to finally plant the stake in the ground * Action creates clarity, not the other way around, and why waiting for confidence before taking a big step is backwards * What it felt like to be energetically liberated after years of making hard decisions one at a time * Emily's perspective from the outside: watching Adrienne go from turtling to fully lit up * The woo-woo side of Adrienne that has always been there and is now getting more room to breathe ⏱️ Time Chapters 00:00 Happy Tuesday and outfit swaps 05:00 Mother's Day recaps 09:51 The throttle heard round the internet 12:42 Losing two anchors: divorce and her dad 16:01 Exiting the partnership and why it was time 17:00 Not anti-men, just for women 18:27 Making the brave decision vs. waiting for clarity 20:09 Emily: she was doing this work long before Mike 22:00 Why women haven't invested in themselves the same way 23:38 Being a divorcee and all the other things that add to the work 24:35 Removing owner dependency: the four exits 30:50 A friend to all is a friend to none 31:36 Picking a card (and manifesting perfectly) 31:56 Going all in on the woo 34:02 Sandbox vs. ocean 37:15 You never have perfect clarity before the hard decision 43:41 Action creates clarity, not the other way around 45:22 Unfailing belief that everything works out

Everyone Pushing Back On You? It Might Be Your Fault.

When you're trying to move a business forward and the people closest to you won't budge, it is one of the hardest leadership situations there is. Especially when those people are a partner, a co-founder, or a family member. A listener asked: how do you implement real organizational change when the people around you are resistant, including someone in your family? Adrienne and Emily have been on both sides of this. They get into all of it. What they cover: * Why resistance from partners usually starts with you pulling back before they even push back * How to build a vision compelling enough that people actually want to follow it -- and why most leaders skip this part * The difference between announcing a change and selling a change, and why one works and the other doesn't * If you're shrinking your ideas to make them more palatable before you even share them, you're surrounded by the wrong people * What healthy partnership dynamics actually look like: clear ownership, immense trust, and always knowing who gets the final call * Why 50/50 partnerships often create stalemates -- and the structural fix for it * What to do when family is on the team and you're avoiding a necessary decision to protect the relationship * The energy question: are the people around you raising your ceiling or quietly lowering it? * Why your identity slowly shifts to match the average of the people you spend the most time with -- and why that should scare you into being more intentional about who's in the room Submit a question: sortabossypodcast.com [http://sortabossypodcast.com] Read Adrienne's article on communal misery. [https://open.substack.com/pub/adriennedorison/p/the-culture-of-communal-misery?utm_campaign=post-expanded-share&utm_medium=web] ⏱️ Time Chapters 00:01 Welcome and banter 13:01 Today's question: how do you implement change when partners and family members resist? 14:28 Start with the vision -- everything else is a sales pitch 16:00 Pushback vs. pullback: why resistance is often your own energy coming back at you 19:00 Emily's take: if you're constantly dimming yourself, you're in the wrong room 20:39 When you're not even excited about your own idea before you share it 22:01 You slowly become the average of the people around you 24:02 Making conscious choices about who gets to be in your orbit 25:24 What Adrienne knows about the person who asked this question -- and what she sees 26:24 Finding synergy in a partnership without abandoning who you are 28:31 How to communicate with partners before you take it to the team 30:17 Leadership has to pull the team forward -- not fight itself in front of them 31:00 What the best partnerships actually look like: ownership, trust, and a tiebreaker 31:38 Why 49/51 beats 50/50 every time 32:45 The tiebreaker board member role -- and when to bring one in 33:35 If you have decision-making authority, use it 34:26 When family is involved: get a mediator, not a miracle 35:06 The business has to come first if you want it to survive

Be Bored and Rich: What Entrepreneurs Get Wrong About Passion, Purpose, and Resentment

Resentment in business does not usually arrive all at once. It builds. And by the time most people name it, it has already started spreading to the team, the clients, and the work itself. Emily has worked alongside Adrienne for almost 10 years. She has watched the seasons shift. She has always had questions. In this episode, she finally asks them out loud. What they cover: * Whether Adrienne has actually resented her business -- and what she's willing to say honestly about that * The martyr trap: stopping your own paycheck to protect the team, and why the team never asked you to do that * Why making huge decisions based on boredom is usually a trap * Why "be bored and rich" is actually a legitimate strategy * What happens when you make your business responsible for your purpose, your identity, your joy, and your sense of self. * How Adrienne's work with The Adventure Project changed how she thought about money and what the business was actually for * Emily's perspective: what it looks like to watch a business owner disengage from the outside, and what she's had to learn about when to hold the line and when to let go * Where to start when resentment is building: values, communication, and not letting it sit Submit your own question: sortabossypodcast.com [http://sortabossypodcast.com] Learn more about The Adventure Project: adventureproject.org [http://adventureproject.org] ⏱️ Time Chapters 00:01 Welcome and banter 07:20 Emily asks the question she's held for 10 years 08:44 Adrienne's honest answer 10:30 The martyr trap 13:45 Resentment vs. boredom 14:39 Be bored and rich 15:06 When the business becomes your everything 19:32 The Adventure Project and why it changed how Adrienne thinks about money 24:10 Fund great nonprofits -- don't start your own 26:00 What disengagement looks like from Emily's side 30:11 Where to look first when resentment is building 33:23 The cycle of doom 34:19 Don't ignore it. Don't blow it up. Investigate it.

You Don't Really Need Those Three New Hires

You don't actually need to hire three people. You probably need to stop thinking in extremes first. This week, a listener asked the question, "I need an EA, an ops person, and someone for client delivery -- but I only have the budget for one. Who do I hire first?" The answer is not who. It's what. And it's probably sooner and smaller than you think. Adrienne and Emily break down how to actually make this decision, why most people wait too long to hire anyone, and what to do if you can't afford a full-time person but genuinely can't keep doing everything yourself. What they cover: * Why "I can only afford one hire" is usually a thinking problem, not a budget problem * The gig economy case for hiring smaller and sooner instead of waiting for the full-time budget * Why three separate roles might actually be one person -- and how to figure that out * Stop hiring by title. Start by identifying which activities need to come off your plate first * The two ways a hire actually generates ROI: they do revenue-generating work, or they free you up to do it * Why freeing up your time only works if you're actually spending that time on something more valuable * How to figure out whether to hire for EA, ops, or delivery -- and why the answer depends on where your time is actually going * Delegation is a muscle. Don't start with the 100-pound weights * What energy drain has to do with who you hire first * Why AI agents are not a shortcut if you can't already delegate clearly to a human Submit a Dear Bossy question or listener question: sortabossypodcast.com [http://sortabossypodcast.com] Follow Adrienne on Instagram [https://www.instagram.com/adriennedorison] ⏱️ Time Chapters 00:01 Welcome and banter 09:33 Today's question: EA, ops, or delivery -- who do you hire first when you can only afford one? 10:02 Why one size fits all doesn't work here 11:21 Stop living in all-or-nothings: you don't need a full-time person to start 12:15 The gig economy makes smaller, sooner hiring more accessible than ever 13:35 It might not be three people -- it might be one person with overlapping strengths 16:10 The only two ways a hire actually generates ROI 17:59 Track your time first -- you cannot make this decision without the data 18:57 Delivery vs. EA: which one actually opens up revenue capacity? 19:26 Delegation is a muscle. Start with the five pound weights 21:04 Hire for what drains you most, not just what takes the most time 22:19 AI agents are not a workaround if you can't delegate clearly to begin with 23:45 How to figure out what to automate vs. what actually needs a human 24:41 The time tracking case -- know exactly how many hours you need before you hire 25:34 Final thoughts: start smaller, start sooner, and use your freed-up time intentionally