I Have 8 Kids, Run a 27-Person Company, and Have a Side Hustle Web Start-up. These are my Top 5 Time Management Hacks.

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Sometimes when I talk about all the projects I have going on, I get the snide remark, “You must not have kids.” And while that’s a true assumption — I don’t have kids — it never really sits well.

The choice to raise children doesn’t have to mean giving up every waking hour and all your entrepreneurial aspirations. It just means you have to be more intentional on how you spend your time.

But since I’m obviously not the best qualified to talk on this subject, I brought in someone who is.

Bryan Orr is a self-described “blue collar entrepreneur,” who runs an award-winning local service business, an online start-up, and has a family of 8 kids.

Update #1: I’m no longer a non-parent, though still have a long way to go to catch up to Bryan.

Update #2: Bryan was a guest on The Side Hustle Show talking about how his new HVAC training podcast has turned into a healthy side business.

Enter Bryan:


How can a 31-year old guy run a full-time service business, side hustle a web start-up, home educate eight kids and still have time to relax, read, and have fun?

The answer (of course) is that is that it is not possible to do it alone, but with help and structure it’s actually not only possible, but it’s really no big deal.

I have the same 24 hours in a day as everyone else.

1. Agree on Foundations

If my wife Leilani was not totally on board with our lifestyle and choices, my life would be utter chaos (visit us at dinner and bedtime and chaos may still be a good description).

She views her role in our family as a passion and calling, and when we talk about where we are headed as a family, we are on the same page. The truth is that she has her finger on the pulse of our home and treats home life with all the focus and gusto of a startup founder.

This level of commitment and focus on common goals didn’t happen by accident.

Leilani and I communicate about the foundations that we build our life on and what we are willing to sacrifice to reach our goals. It doesn’t mean we don’t have conflicts or disagreements, it just means we always face the same direction at the end of the day.

The result is a home that is run with a purpose and everyone is clear on the game plan.

For us, that means training our children in character and intellectual discipline at the expense of other personal comforts. We live in very close quarters, we don’t keep a lot of things that require maintenance, we drive a 15 passenger van (it’s a real beauty), and neither Leilani or I have any time-consuming regular hobbies.

The people closest to you will often be very different, but you must be clear on where you are headed.

Whenever you choose an atypical lifestyle you will get friction. For us it’s things like being able to go to “Adults only” events. Many of our friends and family cannot relate to how difficult it is to carve out time and when you have such a big family. For us it means saying, “Thanks, but no thanks,” more often than not.

We had a really sweet couple that we just met invite us to a weekly get together in their home. They said, “Oh yeah, your kids can come,” but when I told them we have 8 kids, they awkwardly changed the subject.

In order to deal with the critical voices both inside and outside myself, I need to rely on my internal why and stay the course we have chosen.

Nick’s Notes: What Bryan is describing is not much different from the sacrifices you might need to take to get your side hustle off the ground, and the funny looks you might get from friends and co-workers:

“Why are wasting your time on that?”

“Dude, we never see you anymore.” 

“When are you going to get a real job?”

2. Motivate More Than You Manage

The only way I can train leaders to successfully take over my core roles is to give them ownership of the process and outcome.

Motivation takes trust and trust takes time; it doesn’t happen overnight.

For example, it has taken me 9 years of hard work to get my service business to a place where I have people in place who can cover all of my roles with the level of excellence our customers expect.

I believe in process and training, but more than that I believe in showing people that they will be allowed to grow and self-actualize in the context of our business.

No amount of coaxing or pay or raises will make people care if they don’t believe the work they doing is significant and meaningful.

Having people on your team who understand and believe in where the company is headed means leadership from bottom up. When everyone is willing to lead themselves first, it makes for much fewer fires and issues.

We achieve this by hiring for character, values, and personality and not skills or tasks.

The best example is the way we hire technicians. I almost never hire experienced techs, I much prefer to lay out the honest job path for becoming a technician and hire and train anyone who wants to walk that path so long as they demonstrate the character and personality to do it. In other words, hire people who are excited about becoming the best and helping them become the best version of themselves vs. hiring to get a job done.

Nick’s Notes: Building a team you can trust is the BEST way to leverage your time. You may only have 40 hours of available working hours in a week, but with a team of 25 in place, all of a sudden you’ve got 1000 hours of productivity.

3. Don’t Make Excuses

If you and the people around you decide to do something, then DO IT.

Don’t wait, don’t look at Facebook, don’t go to a movie, don’t watch TV.

Get up and make it happen.

This means that sometimes you will wake up very early (I woke up between 3am and 4am every day this week).

You obviously can’t live with this kind of intensity every day, and that is why I find myself saying no to ideas FAR more than I say yes to. But when I find myself about to make an excuse about why I didn’t do something, I try to remember to shut up and do it now.

Nick’s Notes: Here’s my litmus test to see if a task on my to-do-list is really important. If it sits there for weeks or months at a time, it’s obviously not a high priority.

If it was a high priority — by definition — you would have done it already! So why not just cross it off and remove that mental clutter from your life?

4. Be Organized, But Not Too Organized

Let’s face it, if you aren’t using a calendar to track your obligations and lists to track your tasks, you are crazy.

However, I can often waste a lot of time with “planning paralysis” and try to compile my notes in neat groups organized by date and blah, blah, blah. My time would be much better spent figuring out my #1 priority and GETTING TO WORK than it would be thinking about things in the future that may or may not happen.

If you get an idea, GREAT! Unload it into Evernote and keeping working on priority #1.

5. Don’t Whine

I have a 3 year old in my brain. He wants to complain about everything all the time:

  • “Why do I need to work so hard?”
  • “Why don’t people respect my feelings?”
  • “I will never be good at writing” (current three year old brain quote)
  • “I’m too late in the game to start blogging.”

The little whiny-brain-Bryan is the one who causes me to procrastinate, he makes me treat people poorly and he gives me an excuse to watch TV instead of work on what I am actually passionate about.

If I ignore my inner whiner, I get a lot done and I feel great.

Nick’s Notes: I’m definitely guilty of this one.

If I didn’t sleep well, I’ll think to myself, “ugh I’m so tired” … which of course becomes a self-fulfilling prophesy. Instead, if I “tricked” myself into being wide awake and full of energy (maybe by going outside or doing a quick workout), I’m sure I’d be better off.

There are no “secrets” to managing your time better, but there are a lot of truths that will help reduce the days you feel like you “got nothing done” and increase your velocity toward your goals.

Keep hustling, you can do it!

**For those scoring at home, there’s been a new addition to the Orr family since the above picture was taken.

13 thoughts on “I Have 8 Kids, Run a 27-Person Company, and Have a Side Hustle Web Start-up. These are my Top 5 Time Management Hacks.”

  1. Yes I know the whiny 3-year old in my brain who also tells me I am late in the blogging game. But 31-year-old me refuses to believe it. Thank you Bryan for being such an inspiration !!! I only have one son and some days it’s like i CAN GET NOTHING done around him. That’s changing from today.

    The biggest take-away here is that I need to be FOCUSSED. Thank you. Thank you. Thank you.

  2. Great post Bryan. Thanks for sharing. Your experience is inspiration to the average ambitious family man. Like you said, it all starts with a great family foundation and accountability. Thanks again.

  3. wow! Great post! How did I miss this? It’s amazing the connection of raising kids and entreprenuerism. Nick’s insight is spot on. I must learn more from these Orrs!

  4. I love this! Puts things into perspective but also lets you know that things can get done. Truly inspiring story and I wish you the best of luck in your endeavors. Will be following you CLOSELY my friend. I play the time hack myself and I’m actually doing that as we speak. This is the “me” time that I have to create since my wife works. Kind of that when everybody is sleep deal. Take care and thanks again

  5. Wow this is an amazing article! I can definitely relate! This is me all day! I have a family of 7! I get more things done than a single person! We are definitely motivation masterpieces!

  6. The side hustle will make and break some. Those who are determined to prosper will end up becoming a future “side hustle millionaire.”

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