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

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.

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?

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'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."

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.

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!

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.

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

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)

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.

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 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 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.

"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 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.

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.

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).

[dead]

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'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.

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 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.

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.

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'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.