They say that when starting a business, you want to choose something you enjoy doing, or even that you can be passionate about.
Oh come on! Delivery work? Is it possible to enjoy the work, to feel good about yourself, to actually thrive, to feel like a legitimate business person while doing deliveries for these companies?
Ab so freakin lutely!
Maybe it's just me, maybe I'm just weird. I enjoy doing this – I love being an independent contractor and I enjoy the deliveries.
If we just let ourselves think like we are doing something that is good, dwell on the opportunities , choose the enjoyable, and focus on the things that are important, that will play a much bigger role in how successful we can be.

It's too easy to look down on what we do. We can dwell on this feeling menial, or on how the companies take advantage of us. We deal with traffic, grumpy restaurant workers, grumpier customers, grumpierer app support staff. Yes, I said grumpierer. They cut our pay, gas prices go up… we can be miserable.
This website focuses on practical tips, business ideas and strategies for you. But even from a business perspective, one of the most practical things you can do is get your mindset in the right place.
If you're miserable at what you do, all the best tips, tricks and hacks mean nothing.
So how the heck do you start enjoying this work? I came up with five mindset hacks, five ways to adjust our outlook into something that sets us free to enjoy, and even thrive in, our independent contractor delivery work.
1. Embrace Your Status
Dude…. (and I mean that in the most non-gender way possible) You're business owners.
There really is something amazing about that.
We can dwell on how predatory it is for companies to classify us as independent contractors, but I choose to take advantage of that status. I choose to pursue the opportunities.
When they made that decision, they made us business owners. They gave us rights and opportunities that no employee has (they just don't want us to know about those rights, but that's for another post).
They made you the boss.
Know what that means? They made themselves your customer.
That changes the dynamic of the relationship tremendously.
Most businesses take months, or years, to get off the ground. You make a profit from day one. It's an awesome taste of the freedom of your own business.
Embrace that. Enjoy it. Claim your rights. Revel in your opportunity.
You. Own. Your. Own. Business!
Celebrate that one.
2. Know Your Why.
I wrote about this at length earlier. Before you do another single delivery, get real with yourself.
Why the heck are you doing this?
Sometimes we beat ourselves up if we are miserable about what we are doing, but think about this: If you ARE Miserable, that tells me that your why is especially important to you.
So why are you doing this?
Is it to pay off debts?
Survival?
To save for that car, that vacation, that tuition?
To get freedom to do the things things you are passionate about?
Why???
And why is that “why” so important to you? Drill down on that one – dig deep into what is really important.
And then dwell on what this work is doing for your why. How is it helping you meet that why? How can it help you even more?
When we think about the why instead of the what, that's huge. That's motivation.
That's power.
What is your why?
3. Challenge Yourself
Personally, I get competitive with this. I track all sorts of metrics: Deliveries per hour, miles per dollar, profit per hour. I'm always looking for ways to shorten my drives, get deliveries done more quickly, and earn more.
One thing that makes this enjoyable is that I'm competitive with myself. I'm always looking for a way to get faster, to drive less, to find better places to drive, to do better on my hourly profit. I measure things like deliveries per hour or miles per dollar earned and compare those.
When Grubhub cut delivery pay by 12% in my market with their new pay model, and when Postmates reduced fees by 20% over 3 months, I challenged myself to not let my actual hourly profits drop as a result. I took it as an opportunity to show that I was in control of my own outcomes.
It worked.
Know your worth. Know your potential. Declare your value and set goals around it. Challenge yourself to do better, be faster, earn more. I set a goal daily with my 40 cent rule – 40 cents a minute. Don't settle for minimum. Don't feel like you are at the mercy of changes by these companies. Challenge yourself to get better, challenge yourself to overcome changes with these companies.
Empower yourself. Prove to yourself and everyone else that YOU are in control.
Not Grubhub. Not Uber Eats or Doordash or Postmates.
Cement your position as the boss.
4. CHOOSE to Enjoy Yourself
Enjoying yourself is a choice. So is being miserable.
The thing is, there is good and bad in just about anything we could be doing. The kind of work we do isn't nearly as important to our happiness as our attitude.
I like this quote:
Finally, whatever is true, whatever is noble, whatever is right, whatever is pure, whatever is lovely, whatever is admirable — if anything is excellent or praiseworthy — thing about such things.
Philippians 4:8 – New Testament
You can choose what to dwell on. You can choose whether it's the person who didn't tip or the one to tipped generously. Long wait delivery or quick and easy? It's your choice. You can choose whether it's the bad weather or the opportunities that come with bad weather. You get to choose.
I made the decision to upgrade my car a little instead of trading up. It's comfortable and enjoyable. I updated the sound system and a couple of other things. There are more fuel efficient cars out there, but my ability to enjoy the drive was worth paying extra for gas. And it's probably more profitable, because it's easier to stay out there and keep driving when I feel like it.
Enjoy the things you see when you are out. Find the humor in situations. Relish the excitement of the kids who've been waiting for the food. Enjoy the puppy who thinks the food is for them and not their people. Appreciate the smile from the restaurant worker who appreciated you treating them well. Things like these are gold. They can keep you going and overcome the frustrations that can arise.
In the end, that's up to you. Choose to focus on the things that are good out there.
Take Advantage of All That Time in the Car.
I mentioned that I upgraded my stereo. I may have the only 1998 Buick Century on the planet with a backup camera and Android interface. But I spend a quarter of my life in the car and these things allow me to make good use of that time.
How many 9 to 5 workers get paid to learn and develop themselves the way we can? We have all sorts of time to learn and develop through podcasts, listening to information and news, and through Audiobooks. I use the time to learn how to build a business I'm working on, and to learn how to improve this site.
Technology gives us tremendous opportunities to continue to learn. You can say “Okay Google” or “Hi Bixby” to tell your phone to do things for you (or talk to Siri if you are less fortunate). There are almost unlimited resources where you can learn.
If that first question, about the “why,” is a tough one for you, you have time to think through that. You have opportunities to decide the things you are most passionate about. The opportunity exists to think through where that can take your life. You may find you like running a business but you want to take it further than the gig economy will let you. Learn how. You can make plans. Tell your phone to write the plans down (and often it will be more accurate than our own typing).
Or you can just be still and think.
You have an opportunity with your drive time to enrich your life, in whatever way you want to enrich it.
Your Life, Your Attitude, Your Business… They are all What You Make of Them.
I wonder if family and friends feel sorry for me for what I do. Truth is, I probably feel more sorry for them because I wish they could enjoy what they do as much as I do.
I try not to compare myself, but I do see people struggle with this. I'm sure there are plenty who do far better. Is one better than the other? Is it market, or luck?
Sometimes the reasons for success or lack thereof have to do with tactics and how we do things. A little bit is luck. I honestly believe a large part of it is mindset. If we just let ourselves think like we are doing something that is good, dwell on the opportunities , choose the enjoyable, and focus on the things that are important, that will play a much bigger role in how successful we can be.
Besides, life is too short to be miserable.
I do hope that some of these things can help you enjoy your work a little bit more, thrive a little more in who you are and what you do.
Even if it's not delivery related!
Comment Questions:
What do you enjoy the most about your work (whether it's delivery or anything else)? Are there small joys? Big joys? What are your why's and how do those keep you going?
John C Fisher
Wednesday 19th of June 2019
Why? Freedom, pay off debts, save for a better vehicle.
ronald.l.walter
Wednesday 19th of June 2019
Those are awesome, thank you for contributing. I think those are some of the best "why's" out there - a lot of them echo my own. But take those a bit deeper. Why do you want the freedom? What would you do with that freedom? Why do you want to pay off the debt? What will that allow you to do? When we get to the why behind the why behind the why, we drill into the things that are at our core and those things have an even stronger motivation.