To Become The 9-to-5 Entrepreneur

I’ve been there and done that.

I’m not a big shot like Gary Vaynerchuk, nor did I invent a new viral app like #Slack. But I’ve successfully grown a one-man-show freelance web/design gig to a SaaS (subscription) based operation with a 10-person team. Delegation, automation, streamlining, bootstrapping are not buzzwords I see on Entrepreneur.com – I lived through it, I still do, and I will continue to for the rest of my career.

I’m a 9-to-5 entrepreneur. Or should I say, I strive to become one.

You’re probably thinking “I thought people like you want to escape the 9-to-5? Are you drunk?”

I firmly believe in the motto “Work to live, not live to work.” and if I cannot make the time & freedom to enjoy my hobbies and spend time with my loved ones, grinding through one of the most competitive industries is not worth it.

The Bootstrapping Days Are Needed, But Not Forever

Working 16 hour days on a regular basis, working some more on a Sunday, and going to bed at 2AM to return to the office by 8AM was a norm for me. I once got in trouble because I refused to spend Xmas eve with a girlfriend because I had to work (I met my own deadline for the launch of version 4 in 2015 January).

The business was relatively new with only 3 full-time staff on my payroll. I still had to tackle the system upgrade that was critical to the next phase of expansion. Without venture capital funding or parents’ money, I had no choice but to put my own hours in. After all, it was my software, and I knew it best. This was the next big step to improve the customer experience and our product quality while reducing the time burden on our subscription revenue.

For several years, from my one-man-show days to having an established agency, the long grinding hours didn’t stop. I rarely took full weekends off, and I never took vacations.

Then, I had a life again. There was light at the end of the tunnel.

It wasn’t until mid 2015 that I had normalcy back to my life again. I was working 7 to 9 hour days, sometimes even 6 hours a day. I took most weekends off, although I still compulsively checked my emails (I’m still working on this bad habit). The business model was better established, and our workflows solidified. We were utilizing better tools to make our days more efficient without sacrificing quality.

This was the life I wanted (as I became a 30-year-old)

If you’re forever working evenings & weekends, you are a slave to your own work. You are not working to live – you’re living to work, and that’s no way to be. I’m not an advocate of the irresponsible & compulsive YOLO lifestyle… not at all. I believe in putting in hard work to build your future, but the ultimate objective should be to have a life, not to be dictated by work and work alone.

Here’s how I got my evenings and weekends back.

Delegate, Trust, and Avoid Interference

I’m the furthest from a micromanager. I don’t like to look over other’s shoulders. This takes trust, as well as firmly establishing workflow. You can’t expect another person to think like you. But if the training documentation & workflow is well established, it’s easier to be hands-off (minus the routine training & reviews).

Sometimes this backfired. Once, by the time I realized one of my staff was missing procedures, it had cost me tens of thousands of dollars. But, just as you can’t give up on dating because of one bad experience with an unstable person, you can’t let a bad experience shun you from delegation. If one hiree fails, look at why it failed, and fix the problem. Move on.

If you constantly mutter “If you want something done right, you gotta do it yourself.”, you have a system problem, it’s not your team’s fault.

Improve Systems, Learn Better Tools

There are so many efficiency tools out there. You can, and must, get more quality work done in less time. We invested into software upgrades to make our system better, while decreasing the time spent for each website setup (won’t get into the technical details, but it was similar to upgrading a steam engine to a gasoline engine).

Don’t be one of those people stuck with Microsoft Outlook or a paper notepad out of sheer habit. Use Asana, Google Docs, Yesware, #Slack to work better & faster. Reduce time on repeated tasks, simplify your administration to leave time for more important things.

Don’t make exceptions; Change your workflow if needed

If something’s not working, then change the workflow/policy altogether. Every time I made an exception to a policy to appease a customer (when I should not have), or reduce the immediate headache, it backfired – it became an expectation and a norm without any added revenue or profit, or caused confusion later that took up even more time.

Making exceptions to policy is akin to taking a shortcut only to ruin your shoes in the mud and arrive even later than expected. As soon as we stopped making exceptions, our work was contained during business hours and rarely spilled over to the weekend, while managing customer expectations with consistency.

If you have to bother your staff on the weekend, your system is broken

Maybe your documentation or project management system is not being utilized well. Maybe the workflow isn’t clear. Or maybe the workload is too much for the team to physically handle, while your prices are too low. Some steps that should be automated may not be.

Whatever the reason is – if you find yourself having to harass your staff via text or emails over the weekend (unless you do work weekends, as our Realtors® do) you need to look at your systems & workflow to see what the problem is, and work towards avoiding after-hour interactions. You will be happier, as will your team.

It still happens once in a while. Just don’t let it be a norm.

I get it – sometimes you gotta grind out. Truth be told, there are some weeks where we have unexpected issues or irregularities, and I fall back into the 16 hour days and go to bed past 2AM. My team still does overtime once in a while. Never say never.

I’m advocating that these spikes should be incidents, not a norm. Running a business has all sorts of obstacles, and deadlines are real. When shit hits the fan you gotta strap your seatbelts. While these intense times can be dealt with well using agility and extra work, a well-run business should provide you with the work-life balance.