How hard is it to find a job after trying to start your own thing

"irreparable damage to my career."

I am trying to help you with my comment but it is going to be straight. You sound like someone who wants to have the cake and eat it too. If you have the itch so bad, you need to do something about it at some point and there never will be a right time. Trust me on that. Yes, you can take calculated risks etc but overall, there will never be that perfect day.

"Irreparable damage" is too strong of a phrase. That tells me that your itch is not that bad and it is more of a nice thing to do because many others do it. Don't think of it that way. If you truly want to do your own thing, think of it this way. What if you never do it ? Will you be ok with it on your death bed ? If not, do something now. If it doesn't matter that much to you, you are most likely better off just working for someone else.

Having said all this, if you are not sure about how to start your own thing, the next best thing is to join a small company/startup where you learn and are very close to the bottom line. Lot of startups/small companies (under 50 employees) would love to hire failed entrepreneurs.

Source: I have been doing my own thing for almost a decade now after working jobs for a decade. If you are a failed entrepreneur, hit me up. Always open to chatting.

I had a failed business venture and when I was truly ready to give up I found a listing for a job at a startup company that was trying to do something similar to what I was trying to do and I was working for them in about three weeks.

If I was hiring for a startup I’d be more inclined to hire someone who tried to start something and failed that I would be to hire somebody who worked at Facebook and Google and had internalized the processes there.

People might have a different attitude at a big company but I think startups appreciate people who can wear many hats and will figure out how to get something done whether or not it fits the job description exactly.

I was an employee, then did my own thing for 6 years, then recently went and got a job again.

I felt no push-back at all for doing my own thing; in fact, I think it was a positive for most people.

If it was only 6 months instead of 6 years then maybe that would have made a difference (?), but generally I've found that people saw it as a positive sign that I was able to be self directed, work in ambiguous circumstances, etc.

Also as pointed out elsewhere here, the ease of getting a job is often a lot more about your network and who you know rather than your exact experience.

Good luck!

I doubt it would do much harm to your career unless your business ends up facilitating child molestation at scale or something and that’s what you see when you Google the name of the business.

But, the fact that you’ve been thinking about it for 10 years; are asking for permission from a group of strangers; and are already thinking about an exit plan before you’ve even started the business suggests that entrepreneurship may not be for you.

It will obviously be a higher risk proposition than working for someone else. If not having a big brand name on your resume for a few years sounds scary to you, trust me, that will be the least of your worries.

How old are you?

Ageism would be one of my top concerns with regard to re-employment. It is also one of the biggest factors prompting techies to try doing their own thing.

Take a good look at your co-workers. What percentage are beyond middle age? This should give you some indication of your employment prospects going forward.

Fresh out of a 7 year stint in a 'proper job' - a friend and I set up a media company. We pivoted continually and eventually found some mild success with interactive video, but in the end my heart wasn't in it.

I found it really easy to move on to a product job after hat experience, and I have referred back to that 2 year period in nearly every interview I've had since, with good feedback.

Go for it - you'll have heaps to talk about, show and share.

I've heard hiring managers question if a candidate who ran a startup before would stick with the job. Depending on how you present that experience in your resume, it may give the appearance you just want some extra income or breathing room and will bail on the job if/when the startup takes off. Hiring managers may also wonder if you will work on your startup ideas on the employer's time.

I've seen resumes from 20-somethings with history like this: Intern while in university, barista, CEO (or CTO). It can look a bit ridiculous to put CEO on a resume when the company consisted of one or two people. Maybe tone that down to "self-employed."

In many ways it's a plus to have an entrepreneurial stint on your resume. You're basically taking all aspects of design, production, shipping, finances, logistics, legal, etc on your own shoulders, not to mention teamwork and management if you hire or team up with people (highly recommended).

All of these things are skills that employers will like, so long as you can demonstrate in the interview the valuable lessons you learned while doing them. It's all in the presentation. They want you to wow them with the value of your skill set and interpersonal skills, which have just been expanded greatly for free (from their point of view).

They will want to know:

- What roles did you fill, and what you thought about them (they want to know: how strongly do you feel about the position you're applying for vs other options?)

- How did you deal with the day-to-day, and with exceptional circumstances. Are you resourceful and resilient when things go bad?

- How well did you work with others? Do you behave in a professional manner? Do you play the blame game? Are your retrospectives honest, looking for learning points?

As someone who has done this, I'll highly recommend evaluating your circumstances that you have this concern.

Startups need lots of focus, hard-work, runway and luck. Strongly evaluate your appetite to take a shot at it.

I'd recommend a shot but budget atleast 2-5 yrs of staying power.

I had a feeling like that ~6 years ago, took the plunge and failed (with the tiny startup idea that I had).

The only damage this might cause you is that you'd not be accumulating any new money (or there will be less of it, when working part time) during that time. Other than that, it has many more positives than negatives: you will appear as more of a "doer", someone who can think outside of you narrow tech area of work, and you'll also have a stories to tell of how you failed or succeeded. And if that itch is strong enough, you will take take more chances like that and will in those later attempts worry less as you'll know it'll be alright. :)

Just make sure how you will fund the time you are trying to start a business, discuss with people who need to be onboard with this, and also plan the date/time you will start entering the job market should things not work out.

It's emotionally difficult, because you've tasted being your own boss and it's hard to go back to someone else making your decisions. You should have more skills afterwards so you can easily get a job again. As long as you have closure, you can go back to employee. The hardest is if you think your idea can still work, you'll feel like you're giving up on your dream or quitting by getting a job.

My experience: I bootstrapped my company while working full time over the last 10 years. While transitioning to fully self-employed I took contract work to fill the income gaps. Now I'm fully self-employed, but there were times in the past I considered going back to full time employment.

I've gone back and forth a few times, and it hasn't seemed to cause me any problems when applying for new work.

That said, I have a piece of advice: when you list the time you spent working for your business on your CV, don't call out that it was a business you started. Just put it on there like you were a regular employee.

Don't hide that it was your own business if asked, but if you put it on your CV, there are a number of places that will filter you out immediately on the assumption that you'll be quitting to start another as soon as you have the funds.

> I feel like it’s now or never for me to try entrepreneurship

It's never really now or never. Remember that Colonel Sanders was over 60 when he started KFC.

Depends on your field, but when interviewing I tend to get excited reactions to telling folks I run a product with thousands of users, and have experience understanding customer pain and converting that into a product that meets their needs.

There aren't hard data obviously, but some factors to consider:

1. If you go off on your own and never really produce anything visible, it might not back up your claim that you were working.

2. Leaving the "game" during a soft time in hiring might be interpreted as you were probably laid off and then have been unemployed for a couple years, "working on your own thing". I remember seeing this in 2002-3 for people who became entrepreneurs in 2001.

3. Are you on a career trajectory? If so, leaving it will mean you will be on a different trajectory if/when you come back. It could be steeper, start higher, or be flatter, and start lower. If you went away in 1998 for 5 years, leaving a job at $60,000, and came back in 2004 you would be on a trajectory to be making hundreds of thousands. If you went away 5 years ago and are trying to get hired now, you've left a large amount on the table and might not find that job right away. But it's like the market, you can't predict the timing.

Before you jump off, test out your idea with people you will be selling it to. If you don't know any, that's a bad sign, go meet some. If you're afraid to meet them, you won't succeed. Think about how you'll bring the idea to market or find a cofounder who believes in you who can. If your early customers want to invest in you, that may be a very good sign.

depends on how long... 1 year is no big deal... 10 years can be nasty...

depends on the thing... if it demonstrates skills that are highly relevant to employers, then great... if random, then your skills can look atrophied...

depends on the impact... if it got traction of any kind that can be a big win even if the money didn't work out...

I've never had trouble finding work except right after graduating in the early 2000's. My employment has been with software consulting practices, though I have worked for some manufacturing companies as well. Hiring managers generally appreciated my experience as an entrepreneur.

I value that experience because it means that that candidate is going to have many soft skills that come from such an experience. Just make sure to keep your relevant tech skills up to date.

This might just be the sort of people and companies I hang out with, but at my last gig two of the other three developers on my team had failed startup founder in their career history. Ditto the product manager at my current role and some chunk of my local tech friends. Job market is always changing, but it hasn't been an obstacle for people I know, and when hiring I see it as something to talk about but not likely to be a problem.

I am someone who has 'done my own thing' for more than 35 years at this point - i.e. direct contracting with my own clients, occasionally working on some 'side' project I hope I could sell, and even took a FT position here and there when the right opportunity came along.

My feeling is it has not hurt my career at all, and more likely made it better - having your own company, with your own clients and working on lots of things you learn lots of skills you likely won't learn grinding it out for mega-corp year after year.

Other big bonus is, on my resume - there are no gaps - I was either on someone else's payroll (for me less than 5 years of my 35 years of work) or doing my own thing - I never had a recruiter or hiring manager question 'gaps' - on paper I was 100% employed at all times, which is easy to say if you have your own little corp - even if you were technically idle at times.

IMO if you have some money to get thru thru for a while (i.e. you won't be homeless if you don't get a check every two weeks), this is the perfect economy for doing your own thing.

I owned my own company for 10 years. When the business ended, I put myself as an employee of my own company (instead of the owner).

Startup life is about taking risks, seeing things through, timely and honest admission of mistakes to yourself (and possibly investors if big money is lost) and pivoting out of them, not running back to comfort after burning someone else’s cash. There is no “going back”. You have to be the Pirate Captain that points the cannons to the deck and fires.

The “safe” route is to make spare time and build a business during that time using what you have available. At least by the time you seek investment to grow beyond your means, you have demonstrated competent execution.

Someone else suggested working at a startup. That’s certainly a good way to learn the ropes, I’ve done it. I will tell you though, you either distinguish yourself as an entrepreneur or you end up in the “employee” box. The potential upside is if the founders succeed, they might want to invest in your ideas. But even that requires weaning yourself off the company salary.

Find a side hustle you can put sweat equity into.

Keep working your day job. If you have an idea that gets traction eventually you will be able to make the switch.

It will take years. It will be really hard and you will question whether it was worth it.

Don't quit your job. Figure out how to build a manageable project / business you can have full control over. For me this is more important than profitability, and my day job keeps the bills paid.

Staying in the corporate environment will irreparably damage your spirit worse than your feared repetitional suffering for taking risks. People won't respect the slow hustle either, but it's sustainable not sexy so don't be surprised when people don't get it. I don't know if it will be worth it but it's the path I'm on right now and it allows me to accept myself and my situation instead of fighting it and stressing out.

I started something and failed catastrophically. We returned the remaining cash to the investors. VCs are beating down my door to discuss the next thing, and they're introducing me to their portfolio companies to see if I'm interested in jobs.

Starting a company and failing makes it easier to get a job, not harder.

Just came out of this. I can totally see where you are coming from. When I started 3 years back I had same concerns and doubts. But took the leap of faith. You have to trust your skillsets and have some confidence. You have worked for 10 years so you do have good amount of experience. In my experience it was much easier for me to get interviews lined up. And honestly in terms of career progression I am farther ahead than I imagined. One thing that I would improve though is have some idea before jumping off the wagon. Need not have product or funding secured (better if you can) but some direction. Also would highly advise looking for someone to work with unless you are going indie route. It can get lonely and is a roller coaster of emotions daily.

I spent a good portion of the past 40 years hiring people (certainly not full time but as part of my primary responsibilities).

A stint trying to establish your own business would definitely attract a large part of my focus during any interview. I'd need to satisfy myself I knew the truth why you went out on your own. In particular I'd need to believe your reason was excitement about something particular you were going to do; and not because you were running away from something (unemployment; boredom with work; difficulty not being the boss; etc).

On the other hand, I'd be really interested to hear about the thing that attracted you so much and everything about that experience. I suspect I would find that experience an overall positive.

Nobody will care per se that you worked for yourself for a period. It's actually a very common thing, especially consulting and freelancing.

What will come up as a question, with entrepreneurship specifically, is why you stopped and are now job-seeking.

The answer they will want to hear will be something like "I decided that getting a job is more stable and is the best thing for me and my life situation right now."

A bad answer would be something like "we went bankrupt and now I need a job so I don't starve." Since that makes it sound like you're only job seeking to pay your bills for now, until you can save up some money and go back to doing what you actually want (being an entrepreneur).

At the risk of being out of topic, there is a more complete way to think about it. What do you think will be the most painful in the long term: having tried, failed, and suffer the consequences, or having renounced, and regret it for the rest of your life? That second part can be awefuly costly for you own wellbeing.

I'm self employed for 10 years now (one startup, one limited company, then freelance - if that's sounds like a failure it's because it is a bit). 10 years ago i realized I couldn't live with the regret of staying employed. It did not turned out as I wanted to, but I'm better off as things are now that if I hadn't tried (in terms of mental health).

I have spent multiple peruods of my career where I was either self employed or unemployed to spend time working on my own thing. This never seemed to have an impact on whether I could land interviews. Assuming you are in skme form of tech role, chances are you aren't doing any damage to your career whatsoever by going for entrepreneurship. Why would a field heavily founded on entrepreneurship punish entrepreneurs? If anything, some companies want to hire people who were entrepreneurs even if their idea failed.

So many good comments are there, I doubt whether you will be able to digest that information and come to proper conclusion. Entreprenual itch and nervousness about irreparable damage can not co exist. If during your FT job , you have saved enough as somebody said to sustain yourself for 2-5 years and do not have serious debt then to avoid regret at deathbed, go for it . Age also matters , if it is not now , then forget about starting your own business and accept that it is not for you .

I've worked in startups and tech recruiting for startups and whether I was hiring, or hiring on behalf of someone else, I don't think I've ever heard of an entrepreneurial stint as a negative when considering employment history.

Often it's a huge plus as it tells you that the candidate has, at some point, had to think holistically about a business. Doesn't matter if it succeeded or failed so long as you can speak to the experience and the lessons learned.

I've left and come back 3 times in my career. It was absolutely no problem to come back--until my beard turned grey. After that, you are looking at a 6-18 month job search.

P.S. You can do irreparable damage to your career just sitting in your cubicle too. Or have it irreparably damaged by something which is 100% outside of your control.

Nobody can predict the future--if you really want to know what's going to happen, go make it happen.

The economy and where you live / are willing to work will play a much larger role in how easy or hard it will be for you to find a job. Right now, the job market for software engineers is shit. Maybe 8 years ago, when tons of money was slushing around and both big tech and startups were paying well even for new grad hires, you could take career risks much worse than trying to start your own company.

There's no damage. At least you're not leaving a gap in your CV for when you look for a new job after a failed business. It's something you gained experience from, learnt from, and can talk about in interviews. In fact, if you acquired a specialist skill whilst doing the startup, then it can get you head-hunted for certain roles.

If you are a hype entrepreneur that doesn't build anything and crashes and burns, yeah it's bad for your career, those are negative signals. If you are a legit entrepreneur that builds something that sees some market uptake but it just never really reaches critical mass, that's a resume item.

You haven't even started and you're already planning for failure? You should have more faith in yourself.

> how hard would it be to go back if things don’t pan out?

Go back to what? The answer is going to change significantly based on field, seniority & role and what your responsibilities would be as an entrepreneur. Another factor is the brand/prestige of your current resume (Work exp, School etc).

Why would you think the intense learning and broad experience gained from an attempt at starting your own thing would harm your career?

Seems obvious to me and in my personal experience and everyone I’ve seen go try their own thing, can report back that it only helps your career.

> I would be doing irreparable damage to my career.

This is a fear you've completely invented yourself, likely as a defense mechanism against the real fear, which is failure, to convince yourself that it's just "not the right time".

After 7 years of startups and consulting I was able to secure a job with fair market pay without any issues. No one even asked about my history. The skills I developed during my solo stint are my killer feature.

I've never heard this considered as a negative in many years working in SeriesB+ startups and big tech. It's universally a positive.

I've been doing my own thing since 2002. Haven't looked back to a time of being owned by others.

Yes, it will hurt your career. Not irreparable but there is downside risk.

I hire people a lot, and it’s a green flag. People who try their own thing understand what it takes to build a company, and tend to have an elevated ability to make things happen.

If it doesn’t work out, you may lose out on some jobs… but those are the jobs you don’t want. It’ll open up doors closer to what gets you excited — any company that does similar things to what you’re doing will jump at the chance to hire you.

(There’s one exception, and that’s scammy or unethical companies. For example, if you started selling sales leads, I might be meh… but there’s a lot of companies out there who do that and would love to hire you)

"irreparable damage to my career"

You're doing irreparable damage to your soul by not trying it out.

as long as you have some outcomes, some hard evidence to show your skills and achievements made in the entrepreneurial area - it's not different from being an employee in the same role & type of company

I've switched back and forth few times with no problems

Since professional network is the reliable route to good jobs, the future state of your professional network will influence relative difficulty.

"Relative difficulty" because the state of the economy also plays a role. Of course, the state of the economy is not something you can influence. Your professional network is.

All this with the caveat, that 'trying entrepreneurship' is not a business idea. Good luck.

I think like most jobs, it really depends on the thing you started and how it goes

At my previous company, we had a founder of a mobile app startup become a pretty high level PM because his startup gave him very real leadership experience he lacked at his large tech company job previously. But he also had a giant team he built under him, a real product, revenue, investors etc. All that he and his fantastic founder team made happen.

If companies see that, it shows that you can deliver and make things possible.

I have another friend who struck out on their own to be a “Marketing Consultant” and got zero clients, posted some pithy statuses on LinkedIn, and has nothing to show from it except a depleted savings account, and nobody on earth will call him back for job interviews.

It matters what you did, not whether you did it or not

Depends maybe on your idea, but: why can't you start your idea part-time? Work on it evenings and weekends, or maybe drop your employment to 60% or 80%?

FWIW, I count as a failed entrepreneur. I had a hobby system that I worked on part-time, and had a couple of happy customers. I decided to go full-time with it. Turns out: most of the work you have to do has nothing to do with the product or your idea. It's networking, sales and marketing. If that's what you want to do, go for it. For me, nope, not my thing.

After making the decision, it did take me a few months to find the next normal job. I don't thing that was because of trying my own thing, but because I was in my late 40s at the time. Age discrimination in tech is real.

I imagine this varies greatly for different region, cultures and industries.

In Silicon Valley? I can't imagine anyone marking down a candidate for having tried and failed to do their own thing.

Regions that don't have a strong startup culture? I don't know.

I am on my own since 2018. So 6 years at this point. The thing is, I will be honest with you, I am not sure how happy I will be now to work for somebody. I am so not missing all that corporate bullshit. Tiers of management, unnecessary complications of things. Meaning it will be hard for me to find a position where I would be satisfied with the work.

But so far my business is successful and I hope it is going to be that way. And I never stop. I keep making things better in my product. And keep developing new products.

I once had an executive tell me I had been “out of the game an awfully long time” after 2 years doing something else.

This is an idiotic take.

Expect idiots.

But “irreparable damage” it isn’t.