Hi Captain!

I (she/her/hers) am a business partner with Partner (also she/her/hers). We have been running a small business for a few years now. We had one employee who just retired, and we finally hired someone part time. We are equal owners in the company. We went to grad school together and I thought we were friends.

I am more of the sales face of the business for various reasons. I enjoy the networking and advertising part and I calm down any angry customers. She puts in more of the bookkeeping time than me and prefers to be behind the scenes. We equally share in other admin stuff that our new employee cannot manage. I have been making more commission than her for about two months, but it used to be equal.

I have been dating someone for about a year now (he/his/him) who has moved in with me. He and I have a pretty significant age difference (I’m early 30s, he just turned 50). For whatever reason, our relationship… works. We click – and I’ve never felt like this about anyone before, to be honest. Notably, he is more right-leaning than me politically, and I’m more left-leaning… but I studied political theory in college and he works for a lobbying group. We have actually bonded over our differences politically and enjoy engaging in civil discourse about theories, current events, etc.

Sig Other and I do not talk about politics with our friends. We’ve mutually agreed to let sleeping dogs lie on that topic, and typically cheerfully redirect someone (unless we know they’re cool with a discussion on current events!). Neither of us push ideologies on outside parties.

When we had our old employee, Business Partner used to micro-manage their every move. She was constantly checking hours and emails and keeping tabs on her, and complaining to me about things that weren’t done properly. Employee retired… and since then, Business Partner’s focus has been on me.

She gets upset if I leave early to take a cat to a vet appointment. She checks my hours and reviews my work like I’m an employee, constantly texting to see where I am if I’m not in the office and she is lurking around. She works later than I do because (as she’s acknowledged) she goes home alone at night and would prefer to be in the office getting work done. She does leave early for hair appointments and nail appointments, and sometimes for other personal stuff, but she typically rolls in about 10 am, works until 8 pm, and works all weekend. I work 8 am to 6 pm weekdays and I do not work weekends by choice. If there are big projects or a big deadline coming, I will come in on the weekend, but it is not a routine practice for me.

She does take days off for vacations and family travel, but lately I’ve noticed her scheduling ME for appointments when I have travel plans or days off planned. She works bank holidays and guilt-trips me when I don’t do the same. She scheduled an appointment for me when I had a lunch planned with a colleague very high up in our local food chain, and made snide comments about how people in the field, “seem to like [me],” but don’t seem to invite her out. (Colleague called me up specifically to talk shop, invite was clearly only for me – but it’s an opportunity to grow the business!) The tone of the remarks felt… envious. I tried to brush it off.

My work gets done. I pull my weight. But I have a life. I have a lot of close family in the area and I like to take a little time for Sig Other in the evenings. I started my own company with her so we could benefit from schedule flexibility, work for ourselves and our values, and make more money than at our old jobs.

I did not change my schedule when Sig Other moved in. I work the same hours I did before he moved in with me.

A friend of mine recently overheard her in public in a cafe complaining to a group of our colleagues that she’s upset because I make more commission pay than her and work less hours, and complaining that I took three days off after Christmas to meet Sig Other’s family and was traveling out of state. Friend seemed to think she was planning to take some kind of action, but she spotted him and immediately stopped talking. I didn’t confront her about this because I wasn’t sure how to approach the topic. And I wasn’t sure what action she would take.

We used to share a friend group, and now I don’t get invited out with that group. She made an offhand comment after telling me she was going to meet a group of our (mutual?) friends for dinner recently, along the lines of: “Well… nobody wants to hang out with your middle-aged republican boyfriend.” I typically don’t extend invitations to him unless I know ALL significant others are invited, and I don’t believe he’s ever talked about politics with them, but she’s also made it clear she doesn’t approve of my relationship. It felt really awful to clearly not be invited above and beyond any feelings about Sig Other’s political leanings.

I was out on a date with Sig Other last week and ran into them all at a surprise party for another friend’s birthday. It was AWKWARD. Super awkward. And when I mentioned seeing them at the restaurant at work on Monday, she shrugged it off as, “I didn’t do all of the invites, and I didn’t think you were a good fit for that crowd. [Sig Other] is a lot older than everyone else.” But why wouldn’t I want to celebrate a birthday?

I feel a little sabotaged at work and micromanaged by someone who is supposed to share equally in the process of running the company. The general vibe I get is envious, but that sounds so juvenile to say that she’s ‘just jealous.’ I made a commitment to myself to have a better work-life balance this year, and she seems to take it personally when I take time off or don’t work until 8 pm every night.

What’s going on here? What do I do? Am I the jerk somehow that I’m not seeing? Is she actually envious? Do I dissolve the business and start over? Or is there a way to set up professional boundaries and say goodbye to the friendship?

Losing Friends and Losing Business

Dear Losing Friends and Losing Business,

Thank you for writing, this mix of politics, personal life, and work are like catnip to me and I have been thinking about your letter for a while.

There is more than one question buried in your question, so while I preserved the subject line of the email you sent as the post title, I’m going to separate the “what’s going on here” answer into distinct parts:

Your new partner – and his political activities and presumed views – are causing ripples in your social circle and affecting your business.

Your relationship with one particular friend – who is also your business partner – is fraying and you’re not sure whether fixing the friendship or fixing the business relationship is the higher priority or how to go about it. .

Let’s start with the Republican in the room, let’s call him “Rolf.”

Your friend told you what’s happening there: “Well… nobody wants to hang out with your middle-aged Republican boyfriend.” This is not…unclear? If you take your friend at her word that she’s not the only one handling invites (and there’s no reason not to), and you take her at her word that this is the problem for her (and there’s no reason not to), as long as you are with him you might find that her desire to hang out with you outside of work is much less than it used to be and that you and Rolf are less welcome than you once were in certain scenes.

Is this honestly that surprising?

You could argue that many people in the United States are making “I love you and don’t want to fight with you so I guess we will try not to talk about certain things when we see each other” compromises with loved ones (see also employers, coworkers, clients they can’t afford to alienate), so you might wonder, what’s the big deal about including one more dude at dinner, if it means they also get to see their friend?

Well, it’s a complicated calculation with many variables, and the value we assign each is subjective.

One variable is “Affection for Rolf.” Your value is “high,” theirs is “meh?” at best. (If the two of you break up, are any of your friends calling Rolf to see if he wants to hang out? They are not. Meh = AT BEST. ) Rolf isn’t their beloved-yet-problematic relative who taught them to change a tire and kissed their skinned knees and let them drive the snowplow sometimes when they were little. Your amazing chemistry with Rolf isn’t transitive to anyone else, nor are your friends advertising for additional problematic uncle-dads.

Your value is “high,” theirs is “meh?” at best. (If the two of you break up, are of your friends calling Rolf to see if he wants to hang out? They are not. Meh = AT ) That said, a factor in your friends’ calculus is “Affection For You.” They like you a lot and want you to be happy, so putting up with some Rolf some of the time for your sake is a sometimes thing. They remember the times you met their ex who was really into vaping and made the effort to say, “Vaping, like vapor? How interesting. Do go on,” because you loved them. So they try sometimes!

They like a lot and want you to be happy, so putting up with some Rolf some of the time for your sake is a sometimes thing. They remember the times you met their ex who was really into vaping and made the effort to say, “Vaping, like vapor? How interesting. Do go on,” because you loved them. So they try sometimes! Unfortunately a third factor is “Dread Of Dying/Suffering Due To Predictable Consequences Of Right-Wing Politics.” Your dread level is medium…ish? You’re politically aware, you’ve got the baseline dread, but you can still talk about it in terms of theoreticals and find ways to “bond” with someone over opposing views. The more the political situation deteriorates, the more applied theories come with non-theoretical body counts, the more the dread overtakes affection. To list a few examples:

Are any of your friends queer, transgender, an immigrant, not white, not Christian, not wealthy, disabled, poor? Slide the dread counter immediately to infinity and roll 2 D8 for physical and mental damage.

Anybody got a uterus? Add another token to the “We’re gonna lose Roe” doom track and draw three “Federalist Society Dipshits” from the Judge Deck. Sexual assault survivor? Make a haunt roll, now.

Need the government to continue setting an absolute floor on how shitty health insurance is allowed to be to keep being alive? Oh hai, you’re me and everyone in my household.

From that perspective, “Not Ever Talking About Politics At Parties” – a pact that, by the way, zero of your friends have agreed to join – is literally the least that Rolf can do to endear himself to them.

If your friends slip and mention a political fact or opinion, are they are inviting The Old Man And The Sea …. Of Eternal Debate to come out and lecture them about Both Sides?

Maybe Rolf isn’t Like That (I hope he isn’t Like That!) but even so, maybe your friends don’t want to have to censor themselves about current events – an arena where there is kind of a lot of happening right now that it might be important and healing and necessary to discuss with comrades – in order to accommodate one guy they don’t necessarily like anyway. Additionally, there’s discussing politics and then there’s doing politics. Rolf is *doing* politics in his day job as a lobbyist, maybe your friends are also doing things to resist his politics? If so, consider that in the stage of authoritarianism where we’re officially “compiling lists of civil servants who are disloyal to the Exalted Leader so that they can be ‘purged’,” and criminalizing protest, maybe your friends are safer if Rolf doesn’t even know their Starbucks order.

Have they/we/I got Rolf completely wrong? I hope so? (You cannot imagine how much I hope so). But are all the oh-so-politely undiscussed politics 100% affecting people within your social circle’s real actual lives? I would wager, yes.

Which leads me to what you can do about this as long as you and Rolf are together:

Recognize that people might have good reasons for how they feel about him and that “Oh let’s just all disagree to disagree while also never talking about it!” isn’t necessarily a good enough compromise for everyone you know. What will you do if “Rolf Not Invited” is the new normal? Do not defend Rolf’s politics or push to have him invited places. When other people invite you somewhere, assume that he is not invited unless he is specifically included and go solo; it shows that you are listening and that you want to be there. In the meantime, nothing is stopping you from arranging your own dinner parties and inviting who you’d most like to see or generally take more initiative in inviting people to hang out for now. If people show up they can get to know Rolf the way you do. If they stay home, well, that’s information that it’s not just this one business friend and your work issues poisoning the social well. Give it lots of time. If you’re happy? Time will tell. If they are wrong about him? Time will tell. If they’re right about him? Welp, time will tell that, too. Recognize that some of the social exclusion could be happening because your friends DON’T want to fight with you or make you feel bad.

People avoid conflict, and one way your friends are avoiding this particular conflict is to avoid you and the whole question of That Guy by not inviting y’all to everything. If you hadn’t happened to run into everybody at the restaurant that night, would you have even known about the party? What happens if we replace “unfairly excluded” with “quietly avoiding conflict”?

Consider that your friends want you to be happy. But they don’t want to spend their free fun time wondering exactly how “right wing” Rolf is. Which one of their human rights, precisely, is this guy lobbying to diminish at his day job? Or, whose human rights doesn’t he particularly care about as long as it gets his other agenda priorities across? When you bond by having theoretical discussions, which are the parts that don’t really bother you? Is he “not that Right Wing?” Great! That’s on him to demonstrate. In the meantime, your friends want to give you the benefit of the doubt, so they are avoiding situations where that might be difficult.

This is, strangely, a way of respecting the agreement – explicit and implicit – to not engage around current events where Rolf is concerned. “Let’s keep things pleasant and not talk about it, or if we do let’s stick to theory,” you and Rolf genially decide. “Yes, let’s definitely not!” your friends agree.

That is not what you wanted to hear, I am sure. You wanted to hear that Rolf is making an effort to keep his views to himself so others probably owe him the same effort and consideration and welcome they would anybody else’s partner. Something about this doesn’t feel quite fair. You’re right, it’s not fair, because yes there are assholes across the political spectrum but no, “both sides” are not “equally bad” and both sides do not have equal power to enact their theories on human bodies and lives and futures. If we’re arguing about theory and policy, but one side controls three branches of government, has the real life power to actually carry out whatever policies it wants and do whatever it wants to anyone anywhere in the world, and that side routinely breaks its own rules, engages in voter suppression, and destroys a few hundred years of checks and balances to enable an openly corrupt leader to get that done? All that “civility” and “let’s agree-to-disagree” and “reasonable debate is the single best way to air our differences” and general whataboutism is coming from the side with the power, so forgive me, but I don’t think the burden is on those who the regime is harming to smilingly prove how “fair” & “welcoming” we are one awkward dinner party at a time. Rebalance the power and maybe someday everyone will get more friendly. Right now? We’re in deep shit, so grab a shovel and help or GTFO.

I know I am being hard on you about this. I truly want you to be happy, employed, and have friends. You asked me, a person who does not hide her “please just tax the ultra-rich reasonably already so we don’t have to eat them” politics for help, and part of that help is to say from the bottom of my heart that framing your conversations with your business partner and long-time friend as “But we’ve politely agreed that we’ll never discuss politics, why are you being unfair?!” or “You are rudely disinviting me and being micromanaging because you are jealous!,” whether those are the words you say out loud or just your point of view of what’s happening, you are missing something incredibly important. This isn’t “oh we root for the blue team and he roots for the red one so we never wear our team shirts on game day, and we chat about sports only in theory” problem. Your friend can be a micromanager at work, a person who is not great at direct communication, a person who would be happier if she didn’t spend so much time at work, you can both be outgrowing the friendship, your business might still need to address its growing pains and revisit whether it’s still a viable and happy-making enterprise for both of you – AND- simultaneously your friends, plural can have an honest, visceral “Hey bud, did you try to bring a fucking fascist into our brunch circle? ‘Cause I’m not sure I like anybody enough for that!“ reaction.

Do you want to have a real conversation with your business partner about anything, ever again? If so, don’t minimize her feelings about Rolf/politics or pretend they couldn’t possibly have a good reason, especially when she is direct about them for a change. Also, don’t minimize her feelings because “What would I do if I knew for sure this friendship can’t be saved?” is a real question in front of you, and Rolfness is a factor in that question on both sides. “Can we still be friends if you hate my boyfriend?” vs. “Can I still be friends if it means having to socialize with a person whose values are repulsive and dangerous to me and mine?” You don’t have to answer these questions definitively, maybe NOT discussing Rolf, etc. at work makes the most business sense, just please acknowledge that this territory for your conflict is at least as likely as the “She’s needs to get a life, she’s just jealous of me and my happiness!” question in the text of your letter.

Still reading? READY FOR PART II?

Let’s talk business and friendship and how there’s still some hope here. Think of this as a free session with Awkward Consulting™. I have sat through, assisted with, documented, and on-occasion facilitated more hours of corporate retreats, non-profit board meetings, Strengths-Weaknesses-Opportunities-Threats (SWOT)-analyses, “Let’s draft a new mission statement using the power of…story!” exercises, ice-breakers, “Our staff told told us things we didn’t want to hear, so we hired these new consultants who said the same things but with more action verbs!” presentations, “The semester starts in a month so good news, we redesigned the entire curriculum you must now deliver!” meetings, performance reviews, institutional performance reviews for accreditation purposes, corporate communications, crisis communications, “We should probably write some things down if we’re going to move from being a Start-Up to an Up-Up company” processes, and plain old project management meetings than I can count. (Literally, I tried to count and I could not.) Can Awkward Consulting™ apply business intelligence to your emotional problems and emotional intelligence to your business problems in a way that maybe saves your business? Let’s find out.

First, real quick: Do you want to work on the friendship with your business partner?

Consider scheduling exactly one recurring monthly sacred fun thing with your friend. You can invite one mutual friend who is fun and who can be trusted to keep it light as buffer, you can use movies, theater, concerts, gallery shows, etc. to provide a ready distraction. The only rules are “Enjoy yourselves doing things you actually like doing” and “Anybody who mentions work has to put $20 in a jar each time they slip.”

When the jar is full, you both get a spa day.

Time for a gut check:

Did considering that fill you with dread? Then don’t do it, and put another tick in the “this friendship might be done” column.

Did it make you feel some sense of “Aw, yeah, I really miss just hanging out with my friend, I know if we could just hang out and laugh like we used to things would be okay!” nostalgia and hope? Then you know where to start.

Great. It’s Business Time. Not that kind of business time. The part where I focus on your business, specifically your work business.

Here’s what I see in your letter as an outside observer:

The business is having some growing normal pains that all small businesses and all “we started as two friends doing a cool thing but now this is really our real day job” businesses go through. Some things would always need to be re-defined and re-negotiated at this stage.

Nobody’s technically the boss, you’re both the boss and no one is the boss, it’s probably time to re-visit or re-create structures, job descriptions, “these are decisions that must be made jointly by consensus” and “these are the sorts of decisions where you are the boss, thank you for handling that and I’ll follow your lead!”

You recently jointly decided to allocate commissions differently, and whatever the good reasons for that the arrangement, it is clearly not working for your partner. (She is making less money than she did before, relative to you, is what I’m getting. Yes?)

(She is making less money than she did before, relative to you, is what I’m getting. Yes?) You are both probably over-estimating your own contributions and underestimating the other person’s contributions, it’s a thing humans do without being bad people, some data-collection can iron that out.

Your business partner has micro-managing tendencies, I’d absolutely believe that, though also as the person who is In The Office vs. Out Meeting Clients she probably ends up with more of the training/supervision/personnel duties. Also, you hired somebody new but it’s not at the point where that person is reducing anybody’s workload, and if she’s in the office more than you are the “being the person who is always ‘on’/available for a new person’s questions” is feeling like an extra job.

Your business partner sounds like she is feeling stuck and stagnant in her role. She’d like to learn more about what you do, she’d like to go to lunch with clients sometimes, she’d like to take on (and learn how to do) some more of the public-facing parts of the business. Any conversations about what to do next would do well to factor in that genuine desire for more variety and growth.

This is all stuff that needs addressed whether or not you stay friends. So what can you do?

Step 1: Plan Some Futures

If your friend were writing to me I would advise her to do exactly the same thing I am advising you to do which is to sit down and figure out a Plan A, B, and C in a way that prioritizes yourself.

Spell out your options, like so:

Hold onto the business jointly, renegotiate your roles and workload and compensation with your friend/partner, and forge ahead into the new decade as a team. Offer to buy her out and hire somebody with really strong admin/operations skills to do her piece of it. Get a job somewhere and sell the business to her or collaborate with her to sell it to someone else/wind it down as profitably you can. Additional options that I do not know because I do not know your work.

Once you’ve spelled out your options, carefully review all the paperwork that established your business (it probably has the steps for dissolving it or selling it in in there or close by), look at all projections and financial statements, do some thinking, and do some research about how to make each option happen with maximum fairness to both partners and minimum disruption to your future employment and financial well-being.

Write down a) numbers and c) timelines and also c) feelings. What do the numbers look like now? What do the numbers look like if you move to traditional employment? When would you have to make a decision to preserve the most options for yourself and be the most fair to your partner? What would success look like in 1 year, 5 years, 10? Which prospect makes you feel the most happy and hopeful? Which option feels the most like a slog with diminishing returns?

If you have clarity around what you want, the discussions you need to have will be both kinder and more focused.

Step 2: Have Some Conversations

Since you still have to work together, I want to focus on option one from the list above (Keeping the business alive as a partnership for as long as you want to work there) and recommend some conversations and strategies to take the Mutual-Bitch-Eating-Crackers vibe in the office waaaaayyyyyyyyy down. Recommendations:

You feel sniped at and sabotaged. In my experience, you will have the best results if you react to sniping and passive-aggressive comments with direct communication and giving the other person an invitation and the opportunity to speak in good faith. De-escalate where you can, replace mean, passive-aggressive drive-by comments with open, professional discussions. When it works, you’ll get co-operation. Where it doesn’t, you’ll get information. Either way, you can proceed with confidence that you are doing the very best anyone can do to try to be constructive and kind. That’s my overall approach.

To that end, ignore the birthday dinner and the Rolf issue in the office. Accept that maybe your social lives will not overlap much right now, make a strategic decision to discuss Rolf as little as possible at work. Definitely don’t try to push this issue and save your business at the same time. You’d like your friend to be happy for you, yes, you “should” be able to talk about your relationship at work, but you have reliable info that this isn’t so, so focus. “Right now I want to focus on work and how we can both be good to each other and ourselves at work.”

You could decide that anything your friend says about you doesn’t exist until she says it to you, but I think a more constructive path is to address the “friend overheard you in the café” conversation head on. “Hey, you’re allowed to vent about me/work to other friends, I get it, but I can’t pretend I don’t know about it. If Mutual Friend could hear you, clients could probably hear you, so can we agree to not air the dirty laundry in public spaces while we work our issues out? I’ll try to be more aware of that, too.” This sounds like a small town or at least a small social and professional scene within that town, so keep conflicts in-house.

Use the café incident (and not the birthday dinner incident) to talk about the general work situation.“I’ve definitely gotten the message that you aren’t happy with some things at work, and like I said, I understand the need to blow off steam, but can we make a time to sit down together and talk about how we move forward in 2020? I don’t want to harp on an awkward moment, but I think some of our discontents are normal business growing pains, so let’s please not lose the opportunity to work on it together.”

Don’t try to talk it all out right then, put a series of blocks of time for “planning meetings” on the joint calendar. Prepare for those meetings as you would for an important corporate event: Take turns assembling agendas and taking minutes, order lunch, do the thing. The formality gives you a structure and structure can help when things are messy and scary.

Step 3: Make Those Conversations Kind And Constructive

Here are some possible meeting agenda/discussion points/problem-solving strategies that aren’t “quit micromanaging me, jerk:”

Before every meeting with your business partner, I want you to write down 5 things she does well and 5 things she takes care of that you absolutely hate doing. There’s a reason you wanted to make this dream happen with this person, so dig down and find that before you speak to her about the conflicts between you. If you get stuck? 5 good memories of when things were happy and functional between you at work. 5 things to thank her for handling. Maybe you are totally incompatible at this stage and the kindest thing to do for everyone is to close shop, but focusing on what you like and respect about each other won’t make anything about that process worse than it already is.

Every single point of conflict between you and your friend at work could probably benefit from asking the other person to articulate their dream scenario. “In a perfect world, where you get everything exactly as you want it, how would you want to handle [commissions][flexible schedules][division of labor][training new person][job-sharing/learning each other’s jobs so we have more flexibility][long-term career and growth planning]?” Make it a habit to spell out the good things you want and might do. Negotiate from a place of dreams and cooperation, possibilities and solutions.

Especially whenever you hit a “you always/but you never” impasse, try framing the question that way: “Can you tell me how you see this working? What would make this actually work for you?” What she proposes might not be achievable or a good idea for you, but at least you can spend most of your time discussing solutions rather than defining problems.

What are the big business goals that make this worthwhile? Are you both staying in the business for the forseeable future? How much money does the business need to be making? What does a great 2020 look like? How do you get there? Does x business practice get you there? Are specific conflicts a matter of style or preference or something that’s cutting into (or helping) the bottom line?

During the Recession Years Of Temping (2000-2003) I briefly worked at a business that had an explicit “We do not talk about coworkers without including them in the conversation” + “We don’t say anything about someone that we haven’t said to them” policy and it was a little cult-like but mostly in a good way? I offer that to you as a possible pact with your business partner.

Job descriptions: Do you have ’em? Do they reflect both what each person is best at and what each person wants to do? Are they full of secret bullshit tasks that accumulated without the other partner knowing? Do they need a red pencil and a thorough “Why do we do x? Does it make us money? Y/N” audit? If one of you left the business or couldn’t work for a while, are things documented so that the other person could step in? Do you need to switch jobs for a month or job-shadow each other? Is the right fit for your talents and personalities to have more overlap and communication or less, and work parallel to each other rather than in tandem? Put it on paper and figure it out.

I do not think a micromanager who is not actually your boss should ever do performance reviews of you, nor would she enjoy your 360 degree rebuttal, but do you both need a structure for setting career goals and talking about them with each other and/or trusted mentors in your industry? Like, literally, once a year do you need to do the most painful and awkward part of a formal performance review where you set individual goals for yourself and then check in each year on how you did and be honest with yourself (but business-honest, I-still-deserve-a raise-honest) and revise your goals for the coming year?

Where possible, apply data. If your coworker routinely working nights and weekends, that can be an indication that her workload is simply too big, that she needs to delegate more/prioritize differently, or she could be one of the people who just likes to haunt the office like a vengeful ghost and guilt everyone else into doing the same. You suspect the latter, but we don’t actually know without some data.“Working the occasional weekend or evening isn’t weird for a small business owner, but if you’re doing it all the time, of course you’re going to be stressed out. Can we try a month of no weekends and no evenings for anybody and try to keep our office culture to 35-40 focused hours/week? Can we also do some detailed time tracking to make sure we’re balancing & prioritizing things right?”

Divide up the most avoidable work as carefully as you divide up the plum assignments. When I worked in corporate life, my little team ended each month with a pile of filing and reporting that had to be done to remain compliant with our contract. It was that hellish combination of too much volume-wise, too intermittent schedule-wise (it came in dribs and drabs), and not urgent enough to keep pretending we’d do it little by little in-between urgent things. I could have delegated it fully to my (amazing!!!!) project assistant, but it would have slowed down the urgent work and also demoralized the shit out of him. I could have done it myself, but, see above. Enter “Business Saturdays”: Once a month on a Saturday morning the assistant and I would meet at the office in our gym clothes, turn on loud music, spend 2-3 hours knocking out the crap and quoting movie jokes in silly voices, go the nearby Y, and then eat a lavish lunch (on me). We were friends who did things outside of work on purpose, so while this is a dystopian tale of corporate hell in many ways (it had to be Saturdays because we were already working All The Hours during the week), it is also a tale of being friends. Your business partner is your friend, and you probably already do a lot of this by rote, but maybe your business could use a monthly sleeves-up, croissants-ordered culling of the things that nobody actually wants to do.

You’ve both done a very impressive thing in building your business, but one thing that happens when you are your own boss is that nobody’s training or mentoring you. Maybe your partner’s a micromanager because she never learned how to manage people. Maybe your client services and sales role means you get to leave a lot of operations management to her but you would benefit from learning more about that side of things. Maybe your employee needs to level up a lot to actually be useful and it’s worth investing some time. Maybe training will give you a structure for setting boundaries, expectations, and direct communication.

Speaking of direct communication, you’re getting a clear message that the new commission allocation isn’t working. Whatever good reasons you had for making that change, is it worth the discontent and hostility that it is fostering? If this means you are bringing in more money for the business, when will she see a corresponding return?

I agree it’s frustrating to feel like you have to answer to your peer about your time like she’s your boss, but it also sounds like she handles your schedule sometimes because she’s answering the phone at home base? You might be able to address some of this by getting stricter about using a shared calendar app [if it’s not in the calendar it’s not happening] and pre-emptively blocking out blocks of time in your app (like evenings) as unavailable every week so she (and your colleague) can’t enter anything there without talking to you first. It might also take some “Oh, Client, that really won’t be possible, my colleague accidentally double-booked me, can we try _____, instead?” maneuvering to make the boundary stick.

When in doubt, ask.“I know that you work a lot of weekends and nights. Is it your goal to have to work fewer hours yourself?” Stop. Let her speak, actually listen to her answers. Make it safe for her to tell you the truth. If that truth is a garbled “I want to work the same hours I do and also have you work nights and weekends,” then you can deal with that (“That isn’t going to work for me, my goal is to keep a much more predictable schedule” + “But also, that tells me clearly something needs re-adjusted in your workload, so how can we accomplish that?”). But don’t assume you know what she wants. Ask and wait for her to spell it out.

Neither friendship nor business is guaranteed to survive, but I truly think that “Hey, it’s been a few years, we made an actual business, so it’s time to regroup and talk about how this is going to work as an entity separate from our specific friendship” is by far the most hopeful approach you could try to take with your business partner. If the friendship really is doomed, if all these conversations go nowhere, or you figure out that you have divergent goals or that you’d be happier elsewhere? Then you’ve got plans B & C & D & E and can make good decisions from there. But I don’t think that de-escalating, being kind, and asking questions will worsen any of the things that are already bad.

This is a long one, and a strange one, and the second in a week where I want to help the Letter Writer but I am not 100% able to validate their POV of events, which is uncomfortable as hell, but sometimes a question itches me like an incubus and this was one of those. Thank you for trusting me enough to take a crack at it. I hope you find something helpful here, Letter Writer. I wish you well and will spare all of us comment moderation and its discontents. 😉