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Does anyone have experience leaving an established job for a start-up? 

I have been with my current company (since college) for 14 years, and am pretty much the most senior person in my role in North America. My "boss" asks me for advice and follows whatever lead I set. I love the team I work with, the job is super easy, the benefits are great (100% WFH), and the pay is good enough for me. It is really a great company to work for. The only issue is that I've been doing it for long enough that I am incredibly bored every day. I probably "work" 20 hours a week, and most of that is sitting in useless meetings. 

The only issue is that I work exclusively with oil/energy clients which is just gross. The upside is that my job is literally to gouge them for as much money as possible, but still I'd rather work on projects that aren't killing the planet. 

My current company is a Fortune 500 company, and I am so established that I could easily end my career (20 years from now) doing the same job and be just fine, with zero concern for any layoff. I could also easily move up if I decide to care about getting an MBA, but I don't really have an interest in being an exective. I'm not a "people person" / "leader". I prefer to do actual work (my degree is in engineering). 

However, a new start-up approached me for a similar position, and that company is focused on sustainable developments in a field which I am super excited about. This is a spin-off from research at my alma mater, and it sounds awesome, but also seems like a huge risk.

I can see much more upside for career growth at a small company, but much more risk since the company might fold once initial financing dries up. I don't know how the salary really compares, but working for a start-up can have massive upsides once you consider stock options.

Who knows if they will ever be truly profitable, or when a buyout will happen? The technology does seem sound (from my initial overview), they have patents in place, and have major corporate investors established, but that doesn't always generate a profitable business.

Do I stay with the easy, boring job with great benefits, or push for something innovative? 

Edited by Heimdallr
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14 hours ago, Heimdallr said:

Does anyone have experience leaving an established job for a start-up? 

I have been with my current company (since college) for 14 years, and am pretty much the most senior person in my role in North America. My "boss" asks me for advice and follows whatever lead I set. I love the team I work with, the job is super easy, the benefits are great (100% WFH), and the pay is good enough for me. It is really a great company to work for. The only issue is that I've been doing it for long enough that I am incredibly bored every day. I probably "work" 20 hours a week, and most of that is sitting in useless meetings. 

The only issue is that I work exclusively with oil/energy clients which is just gross. The upside is that my job is literally to gouge them for as much money as possible, but still I'd rather work on projects that aren't killing the planet. 

My current company is a Fortune 500 company, and I am so established that I could easily end my career (20 years from now) doing the same job and be just fine, with zero concern for any layoff. I could also easily move up if I decide to care about getting an MBA, but I don't really have an interest in being an exective. I'm not a "people person" / "leader". I prefer to do actual work (my degree is in engineering). 

However, a new start-up approached me for a similar position, and that company is focused on sustainable developments in a field which I am super excited about. This is a spin-off from research at my alma mater, and it sounds awesome, but also seems like a huge risk.

I can see much more upside for career growth at a small company, but much more risk since the company might fold once initial financing dries up. I don't know how the salary really compares, but working for a start-up can have massive upsides once you consider stock options.

Who knows if they will ever be truly profitable, or when a buyout will happen? The technology does seem sound (from my initial overview), they have patents in place, and have major corporate investors established, but that doesn't always generate a profitable business.

Do I stay with the easy, boring job with great benefits, or push for something innovative? 

What's your life situation like (family, home, kids)?

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A lot would depend on life/home situation.  I am in a similar boat to OP though, as I’ve worked my way up in the same company since after high school.  It would be difficult to make that move to another job, but especially as start-up.  But I do speak for job fulfillment, and that it is important if you enjoy what you do.  

A word of caution though.  One of my wife’s biggest clients was offshore wind here in Maryland/Delaware.  It dried up very quickly once certain legislation was passed, and a big federal agency was about to approve an offshore wind farm too.  Sustainable energy is a risk to jump to.  

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It depends on priorities and how much leeway you have to take a risk. If fulfillment in your job is a priority and you have enough networking skills and talent and experience to come back to a comparable position, sure go for it. If you aren’t in that situation, I’d say the grass isn’t always greener and it sounds like your current job is fine.

But for me personally, I don’t need to be fulfilled in a job. I get that in my church, with my family, and with my hobbies. My job is something I do the best that I can to collect a check and benefits and then I don’t care at all after I leave/logout. That’s your crucial question IMO.

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12 hours ago, MWil23 said:

It depends on priorities and how much leeway you have to take a risk. If fulfillment in your job is a priority and you have enough networking skills and talent and experience to come back to a comparable position, sure go for it. If you aren’t in that situation, I’d say the grass isn’t always greener and it sounds like your current job is fine.

But for me personally, I don’t need to be fulfilled in a job. I get that in my church, with my family, and with my hobbies. My job is something I do the best that I can to collect a check and benefits and then I don’t care at all after I leave/logout. That’s your crucial question IMO.

 

Depends on where you find "fulfillment" in a job as well too maybe.

 

For some people, that's just "climbing the ladder" or whatever.  Just "gain better title" and "earn more moneys".  And i don't really care about that (more money plz tho imo).  But for me, it's about doing something that is actually really interesting to me.  Something that challenges me and pushes and allows me to continually learn and grow and do new things.  I'm gonna spend most of my stupid waking hours doing this ****...i want it to be something i care about, or can get invested in and excited about.  I want new things, new problems to solve.

I made a jump a while ago from something i made more money at, to go back to school and do something else where i now make less money.  Which sucks, but it's also great because i don't just sort of sleepwalk through the majority of my day.  Or at least...not always.

 

But yeah, that's the crucial question when it comes to actually jumping out on your own as a small business like that.  How much does personal fulfillment matter, because your personal stress is going to skyrocket...and that's going to have an impact on all the other "clocked out" elements of your life.  Family, friends, hobbies, whatever.  When you start your own business, it's a struggle and pretty all encompassing until you can getting it really humming along.  Your work/life balance goes to "same same".

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On 6/24/2024 at 3:45 PM, Heimdallr said:

Does anyone have experience leaving an established job for a start-up? 

I have been with my current company (since college) for 14 years, and am pretty much the most senior person in my role in North America. My "boss" asks me for advice and follows whatever lead I set. I love the team I work with, the job is super easy, the benefits are great (100% WFH), and the pay is good enough for me. It is really a great company to work for. The only issue is that I've been doing it for long enough that I am incredibly bored every day. I probably "work" 20 hours a week, and most of that is sitting in useless meetings. 

The only issue is that I work exclusively with oil/energy clients which is just gross. The upside is that my job is literally to gouge them for as much money as possible, but still I'd rather work on projects that aren't killing the planet. 

My current company is a Fortune 500 company, and I am so established that I could easily end my career (20 years from now) doing the same job and be just fine, with zero concern for any layoff. I could also easily move up if I decide to care about getting an MBA, but I don't really have an interest in being an exective. I'm not a "people person" / "leader". I prefer to do actual work (my degree is in engineering). 

However, a new start-up approached me for a similar position, and that company is focused on sustainable developments in a field which I am super excited about. This is a spin-off from research at my alma mater, and it sounds awesome, but also seems like a huge risk.

I can see much more upside for career growth at a small company, but much more risk since the company might fold once initial financing dries up. I don't know how the salary really compares, but working for a start-up can have massive upsides once you consider stock options.

Who knows if they will ever be truly profitable, or when a buyout will happen? The technology does seem sound (from my initial overview), they have patents in place, and have major corporate investors established, but that doesn't always generate a profitable business.

Do I stay with the easy, boring job with great benefits, or push for something innovative? 

 

Main question i'd ask with this is...in your particular industry (which sounds oily), how flexible is your established role and credentials in terms of jumping back to one of the various oily companies, if things go completely sideways with the Startup?

 

I'd definitely want to understand contingencies in that scenario.  If you have to go crawling back.  Exactly how "hung out to dry" would you be?

 

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I had a big debate about batman today with this girl basically she said batman is the worst superhero bc he's a billionaire and owns the biggest company in Gotham. Sh said he can reduce crime by improving livable wages every time I tell he she's wrong she just screams.

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9 hours ago, Tugboat said:

But for me, it's about doing something that is actually really interesting to me.  Something that challenges me and pushes and allows me to continually learn and grow and do new things.  I'm gonna spend most of my stupid waking hours doing this ****...i want it to be something i care about, or can get invested in and excited about.  I want new things, new problems to solve.

I made a jump a while ago from something i made more money at, to go back to school and do something else where i now make less money.  Which sucks, but it's also great because i don't just sort of sleepwalk through the majority of my day.  Or at least...not always.

I have a ton of respect for people like this. I'm with @MWil23 personally though, and I get my fulfillment elsewhere. Once something becomes a job for me, it doesn't matter how much I love it, I will stop loving it. I work a job I can tolerate, I am good at, pays well, and gives me the time outside of it to get my fulfillment from everything else- hobbies and family, mostly.

But that definitely plays a lot into the answer @Heimdallr is looking for. Do you feel the need to get a lot of satisfaction and fulfillment from your job or not? The answer to that question, plus the ability to retreat should it go belly up and how many people are counting on you for stability in your job, should inform what you do next.

I'll say that I worked at a startup once. There were definitely violations in labor law for how little they paid me, but I was still a student when I worked there so I didn't mind much. The fact that I was still in college also helped me not get too involved in the company, since it wasn't in my field and always felt like I'd move on after graduating anyway. Ultimately, funding got pulled 3 days before Christmas one year, right after we moved everyone to a new office and established salaries for everyone. No recourse, happy holidays. A fine situation for a kid in college, not great for all of my coworkers that had kids or families.

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On 6/24/2024 at 4:45 PM, Heimdallr said:

Does anyone have experience leaving an established job for a start-up? 

I have been with my current company (since college) for 14 years, and am pretty much the most senior person in my role in North America. My "boss" asks me for advice and follows whatever lead I set. I love the team I work with, the job is super easy, the benefits are great (100% WFH), and the pay is good enough for me. It is really a great company to work for. The only issue is that I've been doing it for long enough that I am incredibly bored every day. I probably "work" 20 hours a week, and most of that is sitting in useless meetings. 

The only issue is that I work exclusively with oil/energy clients which is just gross. The upside is that my job is literally to gouge them for as much money as possible, but still I'd rather work on projects that aren't killing the planet. 

My current company is a Fortune 500 company, and I am so established that I could easily end my career (20 years from now) doing the same job and be just fine, with zero concern for any layoff. I could also easily move up if I decide to care about getting an MBA, but I don't really have an interest in being an exective. I'm not a "people person" / "leader". I prefer to do actual work (my degree is in engineering). 

However, a new start-up approached me for a similar position, and that company is focused on sustainable developments in a field which I am super excited about. This is a spin-off from research at my alma mater, and it sounds awesome, but also seems like a huge risk.

I can see much more upside for career growth at a small company, but much more risk since the company might fold once initial financing dries up. I don't know how the salary really compares, but working for a start-up can have massive upsides once you consider stock options.

Who knows if they will ever be truly profitable, or when a buyout will happen? The technology does seem sound (from my initial overview), they have patents in place, and have major corporate investors established, but that doesn't always generate a profitable business.

Do I stay with the easy, boring job with great benefits, or push for something innovative? 

I look at this as 2 separate issues.

First issue is that your current job doesn't offer you purpose or fulfillment and you're bored at work. Second issue is whether you should move to a start up. Regardless of whether you take the job, the first issue is still there and it might be time to look for something internal.

I haven't worked for a startup, but I've worked with startups a ton. Your concerns about not being a people person/leader would become more pronounced because there's way less specialization. Who does what and how they do everything is new for everyone, so it all has to be discussed, and the fewer people there are the further away from the expert you can be while still being the most qualified person in the room.

All of that said, are you sure you aren't a leader?

Quote

I have been with my current company (since college) for 14 years, and am pretty much the most senior person in my role in North America. My "boss" asks me for advice and follows whatever lead I set. I love the team I work with, the job is super easy, the benefits are great (100% WFH), and the pay is good enough for me. It is really a great company to work for. The only issue is that I've been doing it for long enough that I am incredibly bored every day. I probably "work" 20 hours a week, and most of that is sitting in useless meetings. 

I read this and it sounds like it's a good overall situation, but the thing that keeps you there are the people you like working with. You may be more of a people person in a working setting than you're giving yourself credit for. I was in a very similar position in my last job, and the rewarding memories that I have aren't the projects or anything, it's the little ways I was able to mentor other people.

If there's a way you could try out some kind of hybrid working manager role that still keeps your nose to the ground and gives you that sense of "I did something today" while also letting you formalize some of that leadership in the spare 20 hours, that might scratch some of that boredom itch.

And worst case, if it doesn't work, you know it's not for you, so next time you want a job, you can target a big company, plug me in and let me go kind of deal.

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On 6/25/2024 at 7:58 AM, MWil23 said:

It depends on priorities and how much leeway you have to take a risk. If fulfillment in your job is a priority and you have enough networking skills and talent and experience to come back to a comparable position, sure go for it. If you aren’t in that situation, I’d say the grass isn’t always greener and it sounds like your current job is fine.

But for me personally, I don’t need to be fulfilled in a job. I get that in my church, with my family, and with my hobbies. My job is something I do the best that I can to collect a check and benefits and then I don’t care at all after I leave/logout. That’s your crucial question IMO.

I think that is where I am at too. I don't need to be fulfilled by work. Yeah, doing something new and exciting would be fun, but it would also be a lot more stress, and I'm not sure I really want to make work the biggest focus in my life. 

Thanks for the input! @ramssuperbowl99 @minutemancl @Tugboat @MWil23 @naptownskinsfan

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2 hours ago, MWil23 said:

Case in point…Guys we just had over 100 people reply all to an email that was sent out to 1,000 people in the government. It was absolutely glorious.

Shame - that whole mess could have been prevented if just one person replied all saying "please don't reply all everyone".

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10 minutes ago, ramssuperbowl99 said:

Shame - that whole mess could have been prevented if just one person replied all saying "please don't reply all everyone".

LOLOL

Dude, the first 10 people made excuses why they couldn’t attend this completely optional training. Then the don’t reply all brigade. Then someone just hit reply all to the email in 72 point font that said do not reply all to this email in bold and all caps. Then 35-45 people said “remove me”. Then 10-15 people responded with how to remove yourself. This cycle continues for 90 minutes.

Then my supervisor came in off the top rope in our text thread with “Maybe Ramaswamy was right, fire half the federal workforce. This can be the bar!”

It was everything you wanted it to be.

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43 minutes ago, MWil23 said:

LOLOL

Dude, the first 10 people made excuses why they couldn’t attend this completely optional training. Then the don’t reply all brigade. Then someone just hit reply all to the email in 72 point font that said do not reply all to this email in bold and all caps. Then 35-45 people said “remove me”. Then 10-15 people responded with how to remove yourself. This cycle continues for 90 minutes.

Then my supervisor came in off the top rope in our text thread with “Maybe Ramaswamy was right, fire half the federal workforce. This can be the bar!”

It was everything you wanted it to be.

lmao.  This is sitcom level ****.  This is a goldmine.

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12 hours ago, Tugboat said:

lmao.  This is sitcom level ****.  This is a goldmine.

REPLY ALL UPDATE:

30 more reply all emails overnight and into this morning. 

A clarification email was sent out that over 16,000 people are on this thread.

People have now branched off with completely new subject lines and threads, rendering the “ignore” feature and “rules” feature powerless.

Climbing the career ladder here shouldn’t be difficult.

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