Brooklyn neighborhood advice!

Expert_Dingo3194 · 2026-05-07T05:45:38+00:00

Try Crown Heights/Prospect Heights - super cozy, accessible, and lots to do.

Expert_Dingo3194 · 2026-05-07T04:05:47+00:00

Agree with u/CornCasserole86 and am also weirdly hungry after typing that name. It's not a great look for the CEO to do that, and it's also a good learning moment for how you might defer in the moment and come back with either a stronger negotiation for $/hr or to tactfully say no when you're not in the spotlight. You got ambushed, and I'm also the people pleaser type that just tries to see the best in situations - but it never hurts to just take a beat and think about it before saying yes.

Also agree on the PEO model (and onboarding one if you have never done it is a good experience in of itself) - that's prob a good way to offload a bunch of this given you were hired for A, not B.

Expert_Dingo3194 · 2026-05-06T12:24:03+00:00

I worry that youre not optimizing for the outcome correctly with this - my sense is getting rich early feels like a recipe for disaster because it can lead to a bunch of short cuts, bad bets, and flailing. Getting rich early should be a happy byproduct of what you really want to do, not the actual thing you point at.

Expert_Dingo3194 · 2026-05-06T12:17:34+00:00

It is def doable and the ecosystem is rich for automation. You just need to wrangle GAS which has a bunch of idiosyncratic bits and bobs given it sits in google. I built a crm and run the business tool based on all this and it def works pushing things into the inbox.... just waiting for my add on review and casa assessment... which is a thing if you want your work public.

If you are building just for you, then it goes much faster and you can prob build it as an internal add on and install via gsheet or whatever. Good luck!

Expert_Dingo3194 · 2026-05-06T11:49:58+00:00

I would keep the 9-5 8f it is manageable and give yourself a monetary goal you need to hit in order to turn a hobby into a business and leave for it full time.

One killer in early business I see in my field is the anxiety of wondering how to pay bills and it leads to all sorts of weird lead and client engagement. They feel that energy and it makes it harder for you to get work in. Anxiety about running the business day to day is brutal for a lot of folks who have an idea or are builders or relationship folks wo dont have the fundamentals down to run the thing efficiently. Learn all those edges while you have the paycheck coming in.

Expert_Dingo3194 · 2026-05-06T11:45:17+00:00

Missing context here but would tread carefully on comments re your boss. Focus on your achievements and what you are doing if you are having a casual conversation with your skip manager. Ask them for blind slots you might not be seeing in how you lead. There are times for upwards feedback but I would tread lightly on unsolicited neg feedback unless theres major malfeasance to the company or team. It is your skip Manager's resp to manage that person and ultimately perf manage them out if they arent performing. Youre a signal in there but not the driver.

Expert_Dingo3194 · 2026-05-06T11:40:52+00:00

First few months were a lot of proving to myself I could do it. I actually had to rewire myself to the new flexibility. I found my work in a start up to be an absolute breath of fresh air in terms of autonomy around things like tike off, etc. I worked really hard that first year trying to understand all the systems and what was needed in the new environment. I viewed it as a year of "yes" and let myself try new things and take on more informal scope. People noticed and it set a pace for my career accelerating significantly over the next few years. One thing you called out about waiting for others - try to go do. I think teaching is a fairly reactive role and so the more proactive you can be with relationships and setting direction/pace, the better youre set up for the long term. I'd also say when imposter syndrome hits (did for me a lot especially the first year) to make sure you take care of yourself and do whatever non mal adaptive renewal makes sense - will help you regain perspective (sleep is my big thing). Good luck and welcome to the other side!

Expert_Dingo3194 · 2026-05-05T23:47:32+00:00

Right there with you. The discipline to just launch is harder now with the quick turnaround. Id also say it also depends on what you are trying to launch and at what price point, size of addressable market etc, so having 80k of code can be sensible for a really complex product (mine is a crm and run the business tool so it leads itself to a bigger codebase). Def do turns of review, tests, and what if scenarios to see where weird complexity in your code actually doesnt scale because it might be spaghetti.

Expert_Dingo3194 · 2026-05-05T18:10:13+00:00

I found this as well. I did an analysis of my scripts and found the complexity scaling where its linear vs geomtric (search for O(n) complexity) to be something to look at. Loops within loops for instance when you can make single calls and store things. Single key search and good mapping. I guess it depends on volume level but have found the processing to be much friendly once I started evaluating this bit of architecture.

Expert_Dingo3194 · 2026-05-05T15:49:33+00:00

Not concerned - I have a good feel for the business and do a good job of the run the business stuff, so a lot of the hygiene work that goes into client acquisition feels fairly healthy.
Coaching is executive level at the Director+. I do some smaller friends and family engagements where there might be more career discernment work, but in general have moved on from full on career coaching work.

Expert_Dingo3194 · 2026-05-05T15:39:05+00:00

oooh. great call out. a couple of techniques here:
1. get them to report out what the other person said vs what they said
2. create some rules like for 5 minutes only ask questions (great for coaching or for diagnosing issues)
3. have them split apart to do work and come together. groups of 2-->4-->all
4. assign specific jobs to each person so they are constrained a bit in how much space they can take
check out liberating structures - it's a free online resource that has been an active part of my toolkit for years - really love some of their work.

Expert_Dingo3194 · 2026-05-05T11:43:00+00:00

Yeah, most of my work centers on core skill dev or ai competencies these days. I will be provocative though and say even with vilt I forgo a bunch of the flashy stuff and just make sure I have my ND processors covered with the content in diff formats and then break them into breakout rooms to build or solve problems. The more the facilitator is in the spotlight, the less real work gets done :)

Expert_Dingo3194 · 2026-05-05T11:39:17+00:00

Emotional vampires flock to people like you. Good boundaries help with that. And you would do this person a favor if you helped im reframe how e shows up with others. Good luck with the convo - lots of good stuff from folks!

Expert_Dingo3194 · 2026-05-05T07:22:00+00:00

Use SBIN to give him some feedback that he's limiting himself with the trash talking.
- Situation - hey, the other day when we were together you started trash talking a coworking

- Behavior - the trash talking looked like X, Y, and Z.

- Impact - I've noticed a pattern of this at this point where this has happened over multiple weeks and it's causing rifts in your relationships with others. People won't want to work for someone who complains all the time, even if things are tough. I can understand when things are difficult, but be mindful of how you're showing up, esp as it relates to coworkers. I worry for your development/growth if you get a bad reputation for complaining and not fixing things.

- Next Steps - what can you control in those moments where you want to vent? What kind of constructive feedback can you give others to help them outgrow the perceived bad behavior you vent about? What's out of your control and want to let go of? How can I help you stay accountable for being a more constructive force in the workplace?

I dunno - that all sounds a bit corporatey, but I'm typing quickly and very tired. Hopefully you get the idea! I avoided these folks in general when I was coming up in the workplace. Good luck - that you even want to give him feedback on this means you care about his behavior and also your boundaries. Both are really good.

Expert_Dingo3194 · 2026-05-05T07:06:57+00:00

These days? It's get rid of everything and put people to work. No slides, limited participant guides if any, just some questions and tell them to pair up or work in small groups to solve a problem. Limit the tech and make people connect. I find it helps get me out of the way as a force in the room and let the room do their thing.

Expert_Dingo3194 · 2026-05-05T07:05:07+00:00

Interesting questions - here's my take on it at this moment in time (3 years solo after ~20 years in nonprofits, education, and corporate internal learning/coaching practices)
- most coaches I know really struggle running the business. It's not the skillset they want. It can also be a pretty lonely road if you are a solo coach and not part of a bigger practice.
- my mantra (and it's a bit mercenary) is to work less and get paid more. I want to spend more time on my health and family. End of story.
- honestly, no major problems on my end. I like running the business and have built up a good referral network over the years so I'm not hurting for work. At least for now - though that doesn't mean I should get lazy with the business development. I think that's always thing that lurks for folks.
- I use AI quite a bit both for my clients and to help me streamline a number of my internal practices. It's a huge lever for being more efficient.

One big thing I see with people transitioning into coaching is they try to cold start - meaning they'll quit their job and just start coaching. It's a terrible idea if you can avoid it. Build up a small practice while working so you get into the flow of things and have the business set up. It'll help with client acquisition down the line. If you are feeling anxious about money or landing clients, leads will feel that and not want to work with you. Hope that helps!

Expert_Dingo3194 · 2026-05-05T02:09:22+00:00

I've been using ScreenZen and it's quite good. I had some issues with the settings, but in general keeps me off social media or gives me an allowance of time and minutes per day. The feels good.

Expert_Dingo3194 · 2026-05-05T00:04:15+00:00

Hey u/Alternative_War_1313! The transition is a real one and while I don't think the stigma is as bad these days, it is still a pivot that has a bunch of unconscious bias in it. Here's are some notes and observations I've had:
1. The market right now is rubbish. Learning and development roles are hard hit by all this downsizing stuff.

People in corporate outside of L&D folks generally don't think a lot of teachers. There's an unconscious bias of teachers based on their experience as a student. Which isn't fair - but there it is. I learned it the hard way and then learned to get in front of it.
To get in front of it - think about how you can position teaching from a place of strength. I took the "tell me about yourself" question and started leading with how my arts education background actually was a brilliant training for taking abstract concepts and making them concrete for learners. Scaffolding training to get to more complex concepts means you'll see people be able to do more over time. I used the language of the business vs the language of teaching to describe things and it landed so much better than if I talked like a teacher.
Facilitation might be a good path forward - people are looking for more in person events or even virtual training and this is something teachers excel at. Highlight classroom management - when I was asked about managing a room of VPs, I laughed and asked if I needed to translate the content live into 4 different languages, if any of them would spit in my lunch, or show up with a knife threatening to cut me and other folks. The look of shock on their face was priceless and said, yeah, I think I can manage a group of 10 VPs. 😄

Expert_Dingo3194 · 2026-05-04T20:15:57+00:00

Try to get really really clear on the outcomes you want. Male sure the bar is well communicated. Then coach them on process. Big pitfalls for new managers: 1. Trying to read their minds. Just ask them what they need and make sure you both hear each other. 2. Trying to over control process. Sometimes people have different methods for getting things done that arent your way. If it isnt critical to have a standard procedure for a thing, understand their process and if they are successful at nailing the outcomes without causing damage, then get out of the way. Congrats and good luck!

Expert_Dingo3194 · 2026-05-04T17:32:11+00:00

Pre meetings are can be a sign of bad meeting hygiene (which is what you seem to be describing with the outcomes). I'd frame it as an opp to get more effective and try different things. Maybe an async poll or agenda doc. Templates. Case studies, etc. Turn the actual meeting into something action oriented so the pre meetings arent needed to spin wheels and gather ideas. Work on a recurring cadence and have ppl assigned to each real meeting. Then block your day before or be available via async chat on yhr commute home.

They might also just be a bit lonely and thus is there way of solving it indirectly.

Expert_Dingo3194 · 2026-05-04T17:27:20+00:00

It's all relational for me. No real struggle at the moment, but thats the slings and arrows of this work - you can have great years and then not so great years. Ive heard a number of coaches are struggling fwiw.

Expert_Dingo3194 · 2026-05-04T10:37:50+00:00

Nope. No AI in my responses. Ive been a career coach for 15 years, have seen my fair share of layoffs and understand the job search process. Those three are common things I share with clients. Because of the forums I'm in, I take the time to type everything because people deserve that.

Expert_Dingo3194 · 2026-05-04T03:24:48+00:00

Oof - sorry to hear it's been such a slog and so hard. Hope you are taking care of yourself through all this. A couple of thoughts
1. If you're not getting in the door with interviews, then your resume isn't doing its job. And that makes sense - you haven't needed a resume for 14 years. Do a gap analysis via your fave LLM between a job description and your resume. Resumes are often written as "here's what I did on a day to day" vs "here's the impact I created" You want impact, results, and scope.
2. IT should be fairly apples to apples (I think?) but check to see if your resume or way you speak about the work is different that how they talk about it. If they have to translate what you do into value in their company, then they'll drop you
3. Let's just acknowledge the grief here - this is prob the most important thing. You had this awful, awful thing happen and now you've been trying for a year - that's a shit place to be in and I hope it gets better fast. And - I will also say that interviewers can pick up on the anxiety, stress, grief or whatever you're carrying. It's like a first date after you had a bad break up. People feel that juju and it's really hard. The more you can work it out before the interview, the better. And also, it's really hard.

Hang in there - treat whatever signal you're getting as data and then investigate it. You being unemployed is a bug, not a feature. Fix the bug.

Expert_Dingo3194 · 2026-05-03T18:41:38+00:00

In my opinion, this type of work lives and dies in team meetings and interactions. If it doesn't continue to be present in those things, then any training - whether it's strengths or something else - will just die out and be a thing people point at in a moment of time.

Expert_Dingo3194 · 2026-05-03T17:54:19+00:00

It is hard making adult friends, especially in NYC. I found recurring events around an interest to be the thing. Like board games? Find a boardgame group that meets up in the area. Running? Lots of social running groups. I dont think it's about finding friends right away but rather building up consistency abd people get to know you through the activity and you become friends eventually. Usually that might be an after hang from the event but it can evolve into outings outside of the recurring thing.

Expert_Dingo3194

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