Entrepreneurs Seek Advice After Leaving Employment
13 posts across 11 communities in the last 30 days; 15% from r/careeradvice.
“I think I already know the answer, but I’m looking for confirmation. 22 years ago, while I was in college, I started working part-time for a family owned business (US-based.) When I graduated (20 years ago) I went full-time and I’ve been here ever since. The owners are great…”
“I’m 22 and I’d really appreciate some advice from entrepreneurs who have more experience than me. I’ve been running my own e-commerce business for a few years. This year I moved from Italy to the UAE because I wanted to get out of my comfort zone, become more independent and put…”
“the way I thought about this decision at your age was 1) how do I maximize the return I get for any given time spent 2) how do I make this very difficult road of entrepreneurship even slightly easier for myself, given I don’t come from a family with connections or significant…”
Several users are seeking advice or offering encouragement to others who have recently left their jobs and are starting new ventures. The posts often involve requests for guidance from those with more experience, reflecting a desire for mentorship and support during this transition.
SOURCES (51)
“Tomorrow is my last day at my company. I’ve worked there for 20 years. I’m just dropping by to turn in my company ID card, before most people arrive. Then I’m done and am won’t be at the office after about 9am. I plan to…”
“I am a lifelong entrepreneur, never worked a day in corporate in my life and still felt that way. So I wouldn’t call it black and white [re: For the 60+ that retired in their 40s... tell me about it]”
“I think I already know the answer, but I’m looking for confirmation. 22 years ago, while I was in college, I started working part-time for a family owned business (US-based.) When I graduated (20 years ago) I went full-time and I’ve been here ever since. The owners are great, but are more retired than not these days. Their children are a nightmare, which is what is prompting my serious consideration about moving on. I got a dumb degree (advice to the young: get a technical/high paying degree eve”
“Thank you this advice actually changed my perspective a bit… it was really helpful! How long have you been running your practice for and what was your career journey like as well as the business journey if you don’t mind me asking? Also did you do your charted exams? I’m trying to avoid doing them and stop at AAT level 4 but if I really do need to do it to progress I will but I’d rather not make that commitment I think with the nature of working in industry in the financial services sector it’s”
“Let’s see what LLM think of this. The "Unlearning" Friction: People who spend 15–20 years in a corporate environment are conditioned to mitigate risk, seek consensus, and follow structured processes. Startups require the exact opposite: moving fast, breaking things, and embracing chaos. The Lifestyle Small-Business Mindset: Older founders often look for stable, predictable growth to protect their existing assets (mortgages, families). While this is smart for a traditional small busines”
“Hey founders. I had some Monday morning thoughts and am writing this to encourage you to take advantage of your age no matter how old you are. I started my first startup at 22. Sold it at 23. Failed several others until I started another one at 33 and sold at 41. After working in VC I started a venture studio and am now 50. I recently saw a post about the average age of a successful founder that goes IPO and the stereotype of founders being 22 and drop out of school. The data shows that founders”
“I’m 22 and I’d really appreciate some advice from entrepreneurs who have more experience than me. I’ve been running my own e-commerce business for a few years. This year I moved from Italy to the UAE because I wanted to get out of my comfort zone, become more independent and put myself in an environment that would push me to grow. The problem is that right now I’m basically breaking even here. My savings are getting lower, I’m self-employed, and I also need to help my parents financially, includ”
Hey all- I have 20 years in education but needed to take a break to help my ailing father liquidate his business. Getting back into the market, I was able to find…
“Seconding this! They also will never be the main supporters of your business, they don’t see you as a business owner they see you as their friend or family member”
This is great advice. I'd also add that don't listen to friends and family about any aspect of your business, they are not your target audience even if they like the free…
“Quit IT after 25 years back in 2021. I now work alongside my wife running her business. Thought I would miss IT.... I don't...”
“Choose something you enjoy and see yourself doing for the next few years. Business is brutal and can become boring very quickly. If you don’t enjoy what you do it can be unbearable and burn you out.”
Never expect to make money with it and then ask do you still want to do it
“That's tough! I largely built my company so it's a very different feeling than inheriting one, but even after having enough (I'm in the wealth business) I could never walk away from my "Paragon Family" without a very solid, smooth, methodical transition plan in place. I have 3 expectant mother with more inevitably on the way, 26 employees, and 66 family members (and around 300 client families) who I support and bring peace of mind to. My stress and daydreaming of Mexico see”
“the way I thought about this decision at your age was 1) how do I maximize the return I get for any given time spent 2) how do I make this very difficult road of entrepreneurship even slightly easier for myself, given I don’t come from a family with connections or significant wealth? The answer I landed on was going to college, the best college I could manage and the best business school I could manage. I thought, I might as well aim for the one job I think will pay me enough and teach me enough”
Good for you :) I've quit 2 years ago, zero revenue since, life is good.
“Keep it on the afterburner, meanwhile you do what you do. Worst comes to worst it fails and you fall back on your 9-5”
“That is the spirit and very inspiring to know things are great at this point of time”
“Maybe have a little fun with it. You could act excited and say, "ooo, that's such a good idea! What should I do first?" And just ask them follow up question after follow up question until eventually they realize it's not as easy as it sounds. Maybe making them actually think about what they're saying would shut them up without you having to say "stfu" yourself.”
“My dad had a story like this where I was almost a year and he showed up to work and the door was locked. Never thought it would happen to me. I'm in an incredibly steady profession in and incredibly steady industry. I had the stable job in our family. Nothing but praise from my managers on reviews and bonus increase year after year. I thought I'd work here until I retired. I'm in shock. I'm sure I'll land on my feet but dang I'm worried and just beside my self. Pic relate”
“worth it. you will never know your potential once you stop working for yourself”
How did you learn? Did you work for someone prior to embarking solo?
“I'm early 40's. I just rejoined corporate life about a year ago after 10-15 years of owning/operating my own business. Who has done similar and what are your stories and eventual bounce back moment, if it happened? I knew it would be a drastic change and challenge. I approached it as I used to be the boss and solved every problem, but now I have no power and will say yes to every boss request. (There are a lot of bosses.) I don't want to provide too many details, but it's a techn”
“appreciate you doing this, no pitch is refreshing lol. genuine q though - when you were closest to just quitting, what was the actual thing that told you to keep going vs the thing that told you to kill it? trying to build a better gut check for that myself”
“Make a list of your top 10 ideas and for each idea, jot down a description of who exactly would be interested and what "top-of-mind" PAIN is being relieved and/or "compelling" WANT is being satisfied. Your thinking should be on what THEY want and not what YOU want. All successful companies have a map that shows where the BUYERS of their products/services are found on the Internet and how to attract their attention, engage with them, and convert them into "raving" fa”
“Maybe start a problem solving business for people that have problems to solve.”
“I switched from employee to consulting 11 years ago and now run a successful firm. I have 4 kids 7 and under. My biggest piece of advice is to network. That has always provided opportunities for me! Make a list of people who you’ve had contact with that have been ‘warm’ in the niches you’re exploring and talk with them. See what they’re working on, give some value, see potential opportunities. Make connections in a low pressure way for yourself. Right now you’re in your head so don’t overthink i”
“I'm in a similar situation and I'm in my 30s. Sold my cybersecurity firm a few years ago and had to stick around for awhile. That just ended a few months ago and I couldn't be any happier. It was a much more challenging journey than I ever imagined because of all of the typical corporate garbage. Went down the rabbit hole into robotics and I don't think I'm coming up any time soon, lol. It's new, fun, and exciting as hell. Besides that, I've just been embracing hobbie”
“With 2 kids under 3. I'd plan for a business that fits your life rather than trying to build something that consumes it. Your experience is more valuable than your ability to work 16 hour days.”
“Corporate middle manager. Making a good living. Two kids. Also pursuing entrepreneurial endeavors.”
“I starter my own eCommerce business after 18 years as an employee managing some digital and eCommerce business of various global brands. Latest role was eCommerce Director for one of the top 10 eCommerce websites in my country. The only regret? That I did not start my own business muuuuch sooner. The corporate experience at top level only made it harder for me in the first months running my own business, as the latest corporate experience was less hands-on and operational and more focused on int”
“I like to know ownership structure. Family businesses are usually dysfunctional. If they have investors, what types of investors, PE who will suck out the soul, or is it PE that invests in an industry. Is also spend time checking Glassdoor to see what the current employees of the place. Before you apply anywhere, try to locate someone on LinkedIn and connect with them.”
“Should I leave my job to focus on my business at 23? South African Hi everyone, I’d really appreciate some honest advice, especially from people who have been in a similar position. I’m 23F, Black, and grew up in a township in South Africa. I currently work in property investment for one of the top firms in the industry, earning around R59k per month . I also own one investment property that generates about R10k in gross rental income , with roughly R1k positive cash flow after deductions. Over”
“It took me just one day. I just wanted to try two new things - freelancing and building my own business analysis/consulting portfolio because staying in the job took away all my mental capacity. I have thought to just try it out for 6 months. Although side by side job search is on. Do you think 6 months career break will impact my future job prospect?”
“Been preparing for it mentally for about 3 yrs when OG owners made his exit and sons didn’t have the leadership qualities needed to run a business. Started doing side work while I continued to make the drive into a job that offered no work to do over 50% of the time. So I’ve got that sporadic type of work to keep me entertained but certainly can’t live off it. They say if work comes in I’d get a call back but I’d be very surprised if any work does roll in. It’s been so slow for so long the horiz”
“Just want to know how it went. Appreciate any answers. submitted by /u/Maximum_Age_4018 [link] [comments]”
“I (37M) planned to take over my family business but sadly that didn't happen after I left for moral and personal reasons. I got my PMP and a job to at least get out of the business. I am making 2/3 what i made working for my family. I really don't know what to do next to improve myself and get a better paying job to support my wife and family. I have an education degree and my PMP. The business I worked in was retail we were a decent sized mom and pop home depot. I currently work as a pr”
“A lot of advice about side hustles focuses on how to start one, but not much on why people actually stop. From what I've seen, it's rarely just "ran out of time" — it's usually something more specific: picked something that didn't match what they're actually good at, tried to juggle two or three things at once instead of committing to one, or it started eating into their main job in a way they didn't expect. If you've started a side hustle and later dropped”
“This hits different when you're also building something on your own. Started at 16 programming, first business at 19 - the pattern of "naive optimism → failure → real lessons" seems universal for builders. What's the one thing you wish you knew before that first startup?”
“Hey, What's your state? Your goals? In my opinion, the most important thing to do at your age is to understand what you want to do in your life. Set goals first, before taking any action.”
What is your status right now? Maybe we can help each other in some way