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

  Learn more about The Adventure Project: 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 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

Follow Adrienne on Instagram

⏱️ 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

Every business dips. If yours hasn't yet, you just haven't been in it long enough.

This week a listener asked one of the most real, vulnerable questions we've gotten: revenue is down, you need to let someone go, now what?

How do you actually reabsorb their role without drowning, and how do you ramp back up when you're ready?

Adrienne and Emily have both lived this. They get into the full picture, the mindset, the framework, and what it actually looks like inside a small team going through a contraction.

What they cover:

• Why dips are not a sign you're failing, and why one investor won't back anyone who hasn't had one
• The difference between letting someone go for performance vs. letting someone go because the business has changed direction, and why the second one is actually harder
• How to look at your team like a coach, not a friend: who do you need for where you're going, not where you've been
• The 4T framework for reabsorbing a role: Trash, Trim, Transfer, and where AI fits in now
• Why you should do a time audit before you reassign anything
• How to keep team morale up when the remaining people are scared they're next
• What to do when someone has to absorb a role that isn't in their natural strengths -- and why giving them grace and space matters more than speed
• The clean slate exercise: if you were starting from zero, what would you actually build?
• Why limited resources produce better creativity than unlimited ones
• How to leave the door open with people you let go -- and why that matters more than you think

Submit your own questions at www.sortabossypodcast.com

⏱️ Time Chapters

00:01 Welcome and banter

13:16 Today's question: revenue is down, someone needs to go -- how do you reabsorb their role?

13:45 If you haven't had a dip, you haven't been in business long enough

15:40 Contraction and expansion: this is just part of it

16:37 When the business changes direction and good people no longer fit the new model

17:29 How to evaluate your current team against where the business is actually going

18:27 Why financial pressure sometimes forces the business decision you should have made months ago

19:49 Ask yourself: if this were a client's business, what would you tell them to do?

20:16 Start with a time audit -- know what's on everyone's plate before you reassign anything

20:46 The 4T framework: Trash, Trim, Transfer, and where AI comes in

23:28 Reabsorbing tasks into the remaining team: aligning strengths and capacity

24:20 How to keep morale up and make reabsorption feel like an opportunity, not a burden

25:41 Give people grace when they're learning something new -- especially if the previous person made it look easy

27:34 The clean slate exercise: go from zero to one instead of ten to one

30:23 Adrienne's own contraction story and what she had to reabsorb herself

33:27 You're not failing. The metrics just changed.

34:26 How to leave the door open with people you let go