5 Entrepreneurs Reveal How They Started Side Businesses Whilst Working 9-5 Jobs

This is especially useful for anyone who is thinking about quitting a job to start a business. Most of your questions may be answered in these practical lessons of people who started their businesses whilst working 9-5 jobs. It’s a difficult position for aspiring entrepreneurs but with the right ideas and steps you can pull it off too.

If you are looking to hear from other people in your position for motivation purposes, this will be a good read. These are some of the best responses to the topic by users on reddit.

1. psychosid

I am no longer in that position, but I had a 7 AM to 5:30 PM job along with my startup project for about four years. I worked my day job as a land surveyor and draftsman and by evening and night I was starting a photo/video firm.

Those first few years were rough. I’d work most days from about 7 AM until about 5 or 5:30 PM at my day job, and then I’d head out to my secondary job with an appointment or to my apartment to edit.

When I started the company in 2007, I dreamed of it being a full-time gig, but never really thought it would happen. But slowly, over those years until 2011, I found my niche and figured out it was possible. I never took a cent out of my business until I went full-time in 2011. All of the money I made was invested back into the business.

My friends thought I was crazy for working so hard for “nothing.” They thought I’d lost my mind when I resigned in 2011 during the economic slowdown to pursue a “crazy dream.”

Those years of working two jobs were pretty tough. But worth it in the end. Now that I’m four years into the new business, with revenues increasing every year, and hiring new employees every year, I love rubbing in their faces in a friendly way. They’re all stuck at their desk jobs working for terrible bosses, and I’m galavanting all over the state taking photo and video of large estates and ranches for sale.

Worth it.

2. nichesiteazon

I’m in a somewhat similar situation.

Full-time 9-5 job, wife, etc.

I run a few different affiliate websites that are doing around $3,300 per month these days. Mostly passive income, but they still require upkeep.

Also started a website documenting my strategies, and offering services. This has been taking up a lot more time. Hoping to also get this up to the $3k/mo range as well, so between then two I’d be looking at $75k/yr in online income.

Sometimes I’ll get home from work and just not feel like working on my side projects at all. It comes and goes.

I think I want to try waking up early and getting in 2 hours of work before I head to the office each day.

Can’t imagine having kids and trying to pull it off :)

3. docbrain

Full time IP attorney by day (often with far more hours than 9-5). Running Patent Monk (online patent search engine) by night. Along with a side gig ghost writing for a large media company and running a few newsletters.

How do I cope? Honestly I don’t consider it that serious a problem. I get stuff done. I work hard. And when it’s time to relax, I ONLY do that.

I specifically carve time out to read and go out. I play intramurals to release tension. And don’t cook and have meals made for me. (This last point is important. I have a good estimation for how much my time’s worth. So I outsource all the BS like cooking and cleaning wherever the ROI is lower. Admittedly I can afford to do this because I work my jobs, but it also frees up significant time.)

How is business going? We launched  Patent Monk about three weeks ago and have had over 8000+ users. We’re very happy with the results so far. Now to finish building out all these new features users have requested…

Side note: I sleep 8 hours and I have a girlfriend. I do watch some TV but I’m excellent at having it on in the background while I do work. In fact, I’m doing it right now…

4. BBQ_RIBS

Been working a 9-5 job at a growing marketing firm for 2 years now, started as a runner straight out of college. At the same time I began much more seriously pursuing my new side business involving travel sales and logistical solutions for large events.

I’ve spent the last two years grinding at both essentially, the day job is like a startup in itself as I have grown it’s event division from scratch. (0 employees & -163k profit when I started to now we pull 200k per year profit & 4 full time employees). I work directly for the owner in this case and it has proved to be a great experience. Lots of fun and lots of learning, although very stressful, the work is analogous to my company and it gives me strategies that I plug right into my own business. Long hours, 50+ a week, if it’s an event week 60+. Owner knows I have my own business and is supportive for now.

Now while this is all happening my side business (with two other partners) has been consuming nearly every second of my free time. A typical day involves barely dragging myself out of bed for 30 minutes of emails and calls for my own company. Then shower and run to my 9-5. Duck outside for client calls if necessary. Take long lunches to have a meeting or catch up on some work. Leave there at about 6pm, eat fast food or soylent, drive to other office and work until 12am.

By Friday I usually snap and go drinking or whatever until I pass out. I go to my company’s office on Saturday for 4-8 hours depending on the week and then I either pass out from exhaustion or go drink again. On Sunday I catch up on everything else I’ve neglected to do with my life (laundry, food, romance aka call my ex, exercise, see family).

My own business is finally starting to hit some real metrics, 350k revenue, profit not as much as it should but getting there, new clients, new projects, and general growth. Now it’s time to change gears and make the “jump”. I have a Dday set and in about 7 months I will be 100% self employed.

To answer OPs question, yes you can definitely do it. I’m so damn close I can taste it. It’s going to be hard. Really really hard. You will have to sacrifice almost every piece of your leisure time and it still might all be for not. But for every bad day I’ve had, I’ve always encountered someone having a worse day, so just remember to be grateful that you are even free enough and smart enough to even try. :]

5. manygrams

During the day, I work as a data scientist (basically a data analyst that does a lot of programming). I have been doing this for 2 years since graduating from my degree in Mathematics and Economics. My day job has helped me hone my programming and people skills. I have always worked on small side projects, but I have never made an attempt to monetize them before.

My business partner and I launched my current side business about 6 months ago, and things have been going really well. It’s a freemium service that has grown to ~3k active users since we launched in our first city. We just launched in our second city yesterday. Our premium account conversion rate has been decent since we sorted out our pricing model, though I have been thinking a lot about how to improve this further. I take care of building the website, general strategy, and money. My partner takes care of user growth. We have more than doubled our investment, and we’re currently looking for cost-efficient ways of growing our user base.

Very early on, I made a habit of not ever thinking about my side business during my day job. I’ll be honest – it’s very hard to put off thinking about a support request or an idea my business partner messaged me about, but I feel that I’ve done a good job of compartmentalizing thus far. Furthermore, since I have been taking care of all development, I have really improved my programming skills, which has helped me in my day job.

I’m having trouble with advertising. Our service is currently only targeted to two cities, which seems to make advertising a little difficult. We’ve had a little success with Google Adwords and partnerships. We’ve had almost no success with Facebook Ads, but I feel like this might be because we’re not trying hard enough. The majority of our signups come from media coverage and word of mouth. We’ve been looking into Twitter and Reddit ads targeting local subreddits, but it’s too early to report on this. We’re going to try out some physical advertising soon, which I’m excited about. I don’t like the fact that it’s hard to track the efficacy of this kind of advertising, but I’m looking forward to giving it a try. We haven’t found a method with that sweet spot of good ROI and high traffic, but I’ll keep searching.

My main fear is that the business will outgrow me. I really enjoy my current day job and career path, and I want to stay in the field. My plan is to grow my side business so that my involvement goes down over time, but I have literally no idea how to do that. It feels very manageable at the moment, but it has been growing fast enough that I know it will get harder to manage as time goes on. I feel that this will become easier with experience, but this is something I think about a lot.

Follow the discussion on reddit here.