Delegation Challenge – Days 14-30

The delegation challenge ended three weeks ago, so I’m getting caught up on blogging about it to close out the series. I kept up with blogging through this challenge for the first two weeks, but I found that approach unsustainable. So I opted to prioritize doing the challenge vs. documenting it. I kept good notes along the way, knowing that I could catch up on the blogging aspect when I had time.

Working With Magic

I continued working with Magic throughout this challenge. While there were some rough spots, especially in terms of predicting how well they’d handle a request, I felt it was worthwhile to stick it out, especially for the purposes of this deep dive experiment.

Last week I attended a mastermind meeting and shared a 20-minute talk that summarized this challenge. Among most people I talked to who’d also tried Magic, their experiences were similar to my own, with inconsistent result being the main issue. The idea of the service is pretty easy to understand, and its potential is powerful. But the consensus I’ve heard is that there’s some disappointment when Magic falls down on tasks that you might assume would play to their strengths, such as booking accommodations. This creates some friction in allowing people to leverage the service as much as they might otherwise.

I have to admit that’s something I have to take into consideration as well. When considering assigning a task to Magic, I tend to do a quick mental computation that factors in a failure rate of around 15-20% based on my experiences. Sometimes the task is such an obvious choice for delegation that it’s still worth a try, while other times (and especially if it’s a task where I think I might be looking at a 25% or more chance of having it flubbed), that extra concern is usually enough to make me hold back from delegating it. If Magic could get this failure rate below 10%, it would change the calculus of many delegation decisions.

It’s not just the failure rate but also the expected back-and-forth time cost that’s still incurred when a job doesn’t get done.

Last week I talked to one friend from my mastermind group who said he’d given Magic a serious try, but he gave up after finding that they just weren’t able to accomplish what he’d assigned to them.

That said, my personal experience has been that Magic does successfully get the job done most of the time, and they do it well. They’re professional, super polite, and sometimes playful – all of which I like. They always make an effort, and they don’t give up. I find their can-do attitude impressive, and overall I’ve enjoyed working them, enough that I’ve renewed for another month. It’s not a perfect service, but it has helped me a lot.

A Summary of What I Did Via Delegation

Here’s a summary of what I got done via delegation during this 30-day deep dive:

Landscaper – I now have a new monthly landscaping service for my home. They did the initial clean-up work three weeks ago, including planting some new trees and fixing an irrigation problem. Now they’re on autopilot for twice a month maintenance service. They came by last week for their first maintenance visit. I’m happy with this outcome so far.

Hot water recirculator replaced – A broken hot water recirculator was replaced. Magic was able to find a local handyman service to send someone out to fix it. The repairs took about an hour, and the new unit has been working well ever since. Now the water in the upstairs bathroom runs hot within about 10 seconds instead of taking 2 minutes to heat up. It’s nice not having the mental baggage of thinking “I still need to get this fixed” every time I turn on the shower. Now each time I turn on the shower, I think, “Instant hot water is really nice.” In the long run, this may save me money by using less water too.

Old gym equipment donated – Magic arranged for a local charity, Opportunity Village, to come by and pick up some old gym equipment that had been sitting in my garage for the past 11 years. It’s lovely to reclaim that space in my garage – another positive reinforcer instead of a negative/distracting one. Do you have any old junk taking up space in your life that could be donated? With delegation a single text message gets the energy unblocked and the task moving forward towards completion.

New WiFi mesh network – Before this challenge the WiFi coverage was spotty in some parts of my house, even with a range extender. Now there’s a WiFi mesh network working beautifully, and coverage has been consistently reliable everywhere. This opened up some new possibilities that I couldn’t consider before due to the spotty WiFi in some areas, like adding some Google Home Minis to the house (already done). Solving this WiFi problem was relatively easy; it was just a matter of spending the money on a known solution and doing a small amount of setup. Delegation helped move this towards a workable solution. I had Magic do some initial research and compare potential solutions. I love that I’m able to work productively on my laptop in more areas of the house than before. I even wrote this post in a part of the house that previously had inconsistent Internet access, but now it’s solidly reliable. I also did last week’s CGC coaching call from this part of the house with no trouble at all whereas before I couldn’t trust the WiFi to remain stable enough.

This turned out to be a bigger deal than I ever expected. I dismissed the WiFi issues for years as relatively minor. But of course each time I had the experience of working in my living room, I had to deal with the occasional dropped connection. It sucked, but it didn’t suck enough to do anything about it, or so I told myself. It worked okay most of the time. But having it work 100% of the time is way beyond having it work 80% of the time. Being at 100% is wonderful and triggers feelings of relaxation and appreciation. Being at 80% triggers feelings of doubt and annoyance.

Can you think of any annoying issues in your home or workspace that you’ve grown to accept, telling yourself they aren’t worth bothering to fix, even though you’d likely benefit for years by solving them once and for all? Wouldn’t it be nicer to finally get them solved and put them behind you? How much effort would it really take?

It feels so good to enjoy and appreciate solutions versus having to repeatedly compensate for unsolved problems. Perhaps my greatest gains from the whole delegation experience stemmed from solving some simple but persistent problems and enjoying the peace of mind that comes from expecting the solutions to last for years. Putting just one good solution in place, such as the WiFi mesh network, would have been enough to make the entire 30-day experiment worthwhile.

Bikes fixed – Rachelle and I both had problems with our bikes, so we didn’t ride them. Magic located a well-rated local bike shop, and we were able to take our bikes in and get them fixed. Nice!

New accountant – I wanted a new local accountant for my business, someone who can be proactive in helping me grow my business in the years ahead. Magic researched options, found the top reviewed ones, arranged phone calls, and added the calls to my Google calendar. Magic also sent me reminders a couple of hours before each call. When I selected someone, Magic then arranged an in-person meeting with her, which happened earlier today. All of this was handled as part of one $25 request.

Tires rotated – I was supposed to have my car tires rotated about 17,500 miles ago. Magic arranged the appointment, and I took the car in and got it done. I probably could arranged this in two minutes; it’s just a phone call to Costco’s Tire Center, and the rotation service is free for life since I bought my tires there. Of course I’d been telling myself that I could arrange it in two minutes for a few years. Sending a text to Magic actually got it done. This was a good example of stretching myself to delegate something that I genuinely believed would have been more efficient to do myself. I probably spent a little more than two minutes on the back and forth with Magic just confirming things. But this pathway got it done, and the result is what matters. This was a real eye-opener for me, encouraging me to leverage delegation in areas where I’ve been telling myself “I could do this in two minutes” for years while still not actually doing it. I didn’t pay $25 to save myself two minutes. I paid $25 to save myself another year of mental distraction.

New doctor – The last time I went to a doctor appointment was in 2004, which was for treatment for a bad case of Strep Throat. That was the same year I began blogging. I can’t even recall the last time I had a full physical exam (in my 20s maybe), so I’d like to get one and start having more regular check-ups as I get older. I don’t have a good local physician that fits my current insurance, so I assigned Magic to find one. Magic found some options with good reviews, and one of them matched up with a personal recommendation I’d received as well. This doctor practices concierge medicine though, which I’ve never tried before, so I had Magic arrange an initial in-person consult to see if it makes sense to go this route. I’d been telling myself that I “should” do this for years, so this was another case where delegation got things unstuck and moving forward.

New dentist – I figured I might as well assign Magic to find a new dentist for me since I haven’t been to one in years, and I could use a check-up. I delegated this item during the challenge, and Magic did the initial research promptly. I just have to follow up by picking someone, and then Magic can schedule the initial appointment. This is a case where I’ve kept Magic on hold for a few weeks, feeling I’d bitten off more than I could chew (ouch, bad pun) and wanting to clear out some other tasks first. Magic sends me occasional polite reminders to let me know that this item is still open, patiently waiting for me to tell them when I’m ready to move it forward and actually schedule something. This was a good lesson for me as well, reminding me that I can always hit the pause button on certain delegated items till I have the capacity to deal with them. I’m responsible for maintaining the right balance.

When working with an individual VA, you may need to be concerned with load balancing. If you’re paying for a set number of hours, you don’t want to delegate too little, or it will cost you money. And you don’t want to delegate too much, or it could stress out your VA and create overwhelm. I could underutilize Magic and end up overpaying, but I can never realistically overwhelm them because even if I assign them 10 tasks at once, they can just divide the work among multiple VAs. So this gives me the sense that I have unlimited VA power at my fingertips, which is a cool feeling to have.

Massages – Partway through the experience, I had Magic book some massages for Rachelle and me at a local spa. This was another example of something I could have easily done myself, but often when I tell myself that I could easily do something, I don’t actually do it. When I tell Magic to make it happen, it gets done. Delegating a small task instead of doing it myself might seem inefficient sometimes, but delegation usually ensures that it gets done, not delayed. This realization needs to be part of the calculus for deciding what to delegate.

Password manager – As I shared in a previous post, Magic initially fumbled my password manager research request, but even after the ball was dropped, it continued rolling forward. Attempting to delegate this was the opening move in a series of actions that helped unblock this project, which eventually got done. This item showed me that even when delegation doesn’t work directly, it’s still a way to get some stuck energy flowing again. You’re going to experience some waste when you try to delegate, but even fumbled delegation can move worthwhile tasks and projects forward by getting some stuck energy flowing again. So even when delegation appears to be unsuccessful, it can still be effective in terms of generating results. This was a huge eye-opener for me, encouraging me to try delegating some items specifically to get stuck energy moving again, even when I didn’t expect delegation to be particularly efficient.

Asana – During this experiment I got some recommendations to try Asana, an online project management tool. I’ve been using the free version for a few weeks now and like it a lot. I may upgrade to the premium version later, but for now the free version does everything I need, and it supports up to 15 people on a team. I’m mostly using it for my own individual projects so far, and Rachelle and I are using it together to coordinate the CGC logo project. Eventually I can start using this for team projects too. Previously I’d been using Scrivener to manage my projects and tasks, and I still use it for planning and organizing some aspects in greater detail, but Scrivener is a solo tool and not suitable for coordinating group projects. So by switching to Asana, I removed another potential block to delegation and set myself up for a smoother pathway to further delegation. Asana has a bit of flair too, such as unicorns and narwhals flying across the screen when you check off a task as completed; you can disable this behavior if you don’t like it, but I think it makes the service more fun to use.

Managing appointments – I gave Magic access to my online calendar several weeks ago, so they’ve been able to schedule appointments for me (or reschedule as needed). I like that I’ve also been able to give them general directives like only booking phone calls for the afternoon since I like to reserve mornings for creative work. This saves me a little extra time. Sometimes they mess up though, like the time they accidentally added a 13-hour appointment to my calendar (by confusing AM with PM) or when they added something to the wrong day. I quickly caught these mistakes and let them know, but this does stand out as another situation where their accuracy could be a concern.

CGC logo project – This one doesn’t involve Magic, but it does involve delegation. The Conscious Growth Club logo we’ve been using since 2017 is really just a piece of clip art, so I’ve been wanting a more professional logo to use for the group. Initially we tried going with 99designs and signed up for the gold level (about $800). But our design contest only attracted 11 designers, and we didn’t see any initial designs that enough people liked. We decided not to move the contest to the next level, and we got a refund instead. For us the 99designs experience was mostly disappointing. Eventually, however, this led to working with a designer from that same site one on one (but still paid through 99designs), and Rachelle has been working with him to craft a new CGC logo. This project is still in progress, so we’ll have to see how it converges, but at least delegation seemed to be helping it move forward. In this case we’re more concerned about quality than speed, so we’d like to take the time to get a logo we like.

CGC members doing educational segments – Shortly before the delegation experiment began, I leaned into it by inviting CGC members to share a 10-15 minute educational segment about a personal growth topic at the start of our regular coaching calls. I’d previously been doing these segments myself. I like that we’ve opened this up as a way for members to step outside of their comfort zones and share some value with the whole group in a safe and supportive environment. So in this case, delegation created growth experiences for other people.

New health coach – This one I arranged on my own without Magic’s help. This year I want to work on creating more balance in my diet and exercise habits, and I’d also like to get sustainably leaner. So with delegation in mind, I thought, Why not delegate this too? When a CGC member mentioned MyBodyTutor in our forums several weeks ago, I checked out their site. It sounded like a nice fit, so I signed up shortly thereafter. My coach’s name is Matt, and he’s also a certified personal trainer. This coaching is done mostly online with weekly phone calls, and it’s $249/month for the service. I’ve been using MBT for the past 2.5 weeks and have dropped about 5 pounds already. So far I really like it, and I can see why it gets results. (Incidentally, if you’re interested in trying MBT as well, you can get a $100 credit if you mention that I referred you when you do the intake questionnaire, and I’ll get a $100 credit for the referral too. I’m giving MBT a tentative thumbs up so far since I am getting positive results with it, I like the service, and I plan to continue renewing it for a while.)

To me this was a huge amount to get done in about a month… extraordinary even. I’m immensely pleased with all of these outcomes. Just writing them up and reviewing how much got done makes my head spin. It really seemed like a lot to pack into 30 days, even though some of these items are still in progress.

One of the best uses of delegation was to help resolve several nagging issues around the house. It’s amazing how much extra energy gets freed up when small things no longer distract me.

In fact, this freed up so much extra energy that it got me moving forward with an all new creative project to do a group 30-day deep dive together, already planned for August 1-30. I shared some details about that in yesterday’s post: How About Doing a New 30-Day Deep Dive Together?

This helps me grasp that even when I’m using delegation to tackle what appear to be mostly personal problems, like various issues around the house, it frees up more mental capacity that I can flow into creative projects to benefit many other people too. I think it was a good approach to begin on the personal side with this experiment since that’s where I had many identifiable tasks that could free up some stuck energy.

Magic’s Pricing Model

If I could change just one thing about working with Magic, it would be their pricing model. Their pricing model might make sense from Magic’s angle, but from a customer perspective, I find it lacking. I like the per request pricing, which is wonderful. I dislike the monthly subscription aspect, however, because it forces me to estimate how many tasks I’ll want to delegate in the month ahead.

Partly due to this awkward pricing model, I downgraded my account from 16 requests per month to 4 requests per month. So I intend to keep working with them for now, but I also want to dial this back to a more sustainable level.

I can’t predict a month in advance how many items I can expect to delegate. It’s likely to be somewhere in the 4 to 16 requests per month range, but it’s also likely to vary a lot. In practice the gap between 4 requests and 16 requests feels enormous to me. Imagine going from eating 4 meals a day to eating 16 meals a day (roughly every waking hour), and you’ll get a sense of how extreme this gap is. Or imagine going from 4 audiobooks per month (about one a week) to 16 audiobooks per month (one every 2 days). That’s a really big jump from one tier to the next.

As I’ve shared before, I think a more sensible pricing model would be to sell packages of 10, 20, or 50 requests (or something along those lines) with appropriate discounts for bigger blocks. Then let people use those credits over whatever timeframe works for them. When I have a lot to delegate, I might use 10-15 requests in a month. When my delegation-worthy tasks are lighter, I might assign just 2-4 in a month. Why not give me this level of flexibility? If Magic made only this one change, they’d make their service easier to use over a longer period of time.

If I quit Magic at some point, the most likely reason would be that I felt their pricing model was fighting me, and I found a better model elsewhere. Their current approach puts me in a situation where I’d rather not overpay for extra tasks I won’t use (like paying for 16 and using only 10), so I end up going for the tier below what I expect I’ll need. But then I’ll sometimes underutilize Magic’s service by using up all of my credits and then punting any remaining delegation-worthy tasks to the next month when my credits renew. Or I’ll just find some other way of getting those tasks done. This is inefficient for both of us though. I’d rather assign to Magic all tasks that I think they’re capable of, and for $20-30 per task it would be even worthwhile to assign them some doubtful tasks now and then just in case they succeed.

Another decent pricing model would be to have per request prices but without having to specify an exact commitment in advance. So if you assign 1-3 tasks per month, you pay $35 per task. If you assign 4-15 tasks per month, you pay $30 per task. If you assign 16-31 tasks per month, you pay $25 per task. And if you assign 32+ tasks per month, you pay $20 per task. Then just bill me the appropriate amount for the number of tasks I used. I think this would work well, although a greater number of smaller steps would likely work better. If Magic still wants to be paid in advance, then let me put down a deposit to cover the maximum I might expect to spend in a month, similar to adding credit to an iTunes account or a Starbucks card. Then let me specify that if my account balance dips below a certain amount (like only $25 left), Magic can automatically refill it by charging a certain amount to my credit card, like $300. I’d be okay with this arrangement, although I’d still prefer the bundle purchase idea.

Some friction occurs when I have to estimate in advance how many tasks I’ll want to delegate in the next 30 days. That’s hard, especially for someone who’s relatively new to delegation. Why make me do that? Is it really necessary, or can Magic eliminate the need for this extra decision step? In practice when I have 6 or 8 tasks to delegate, it means I’ll only delegate 4 of them. And that means we both fall short of our potential for doing business together.

Note that Magic may change their pricing model, so if you’re reading this a while after I published it, you may want to check their website to see what they’re currently offering.

Reframing Limiting Beliefs

I really made tremendous strides in overcoming blocks to delegation thanks to this experiment.

Some of those beliefs simply collapsed due to confronting them with direct action. I now see how getting a result is more important than controlling the process.

In reviewing the list of limiting beliefs in the previously linked article, I see that there are just a few significant ones that remain for me. The biggest issue I have going forward is guarding against complexity. I have to be careful with the pacing and manner of delegation, so I don’t get overwhelmed with added complexity, like filling up my calendar with too many meetings as I try to move multiple projects forward simultaneously. Presently I don’t see this as a limiting belief though. It’s a real risk to manage.

Building skill at delegation is also something to work on. It would be easy to bite off more than I can chew here, and sometimes I felt like I’d done so during the 30-day challenge. So this combines with the previous risk to emphasize the importance of pacing oneself intelligently. Keep making progress with delegation, but don’t overdo it.

The last major hurdle is finding good people. By working with Magic, I’ve largely let someone else handle that aspect, but of course the results can be inconsistent. So this is another area to work on and another skill set to develop.

My biggest challenge now when it comes to delegation is my imagination. When I look at each project on my plate, I think about how I could slice off some pieces to delegate. The answer is often far from obvious, and there are many ways to slice up a project. I need more practice at imagining how projects can be chopped into pieces that can be assigned to someone else. Or I need to delegate that function to someone else.

Delegating to AI

Although this challenge was about delegating to humans, I still see a lot of potential in delegating more to robots and AI in the years ahead.

I’ve upgraded my collection of artificial helpers this year as well. Before the delegation challenge, I added a Roomba 980 (for vacuuming), a Brava Jet (for mopping), and two HomePods.

This week we also added three Google Home Minis. Google’s AI assistant is vastly superior to Siri – it’s really not even close (sorry, Siri). I enjoy seeing how the experience of working with AI tools evolves over time.

Amazon Prime Day is coming up July 16-17, so that’s also a good time to get Echo/Alexa devices since they’ll probably go on sale then. I might pick up a few as well (maybe an Echo Spot and some Echo Dots), so I can test out that ecosystem as well. Each system has its strengths and weaknesses, and it’s not clear who the long-term winner will be (although I’d currently bet on Google). In the meantime I intend to enjoy the ride over the next several years as all of these systems continue to grow in intelligence and capability.

A funny thing happened yesterday. I asked the Google Home Mini what she thought of Siri. She asked Siri to dance, actually activating Siri on a nearby HomePod in the process, and then Siri responded. I thought to myself, Wow… these devices are now talking to each other. Won’t be long till they’re plotting against us. It’s an eerie experience watching two devices in your kitchen engage in a short conversation, seemingly understanding each other too.

Just for fun try asking a Google Home device, “Are you Skynet?” I thought it gave a clever answer. I actually found Siri’s answer to the same question a bit more disturbing. Siri claimed she didn’t know, but I’m not sure if I believe her.

We’re in a strange and unstable phase in the development of AI and robotics. It’s going to be a fascinating wave to surf, changing year by year. If you don’t keep up with it, I can’t blame you, but these increasingly intelligent devices may hold it against you.


This was one of my toughest 30-day experiments in terms of how much mental effort it required of me. Pushing through the limiting beliefs wasn’t easy. In fact – and I say this without trying to exaggerate – I found last year’s 40-day water fasting experiment to be psychologically easier. Fasting was physically more challenging, but it didn’t run me into as many limiting beliefs.

I gained a lot from this challenge, and it certainly transformed my thinking about delegation. The way I think about delegation now is much different than it was eight weeks ago before I began this experiment. I found my own sense of order by diving into the chaos.

Thirty-day deep dives remain one of my favorite personal growth tools. They can be good for adopting new habits, but they’re also good for testing other modes of living, trying different mindsets, and pushing through limiting beliefs to see what’s on the other side. I sometimes feel that a 30-day trial is a miniature life in itself. It allows me to dive deeply into a mode of living that I might otherwise completely miss.

And again, if you’d like to join us for a group 30-day deep dive, I’m seeing lots of interest already based on the emails I’ve been receiving about yesterday’s post. We’ll be kicking that off August 1st. I’ll share more details about it in the weeks ahead.

Receive Steve's new articles by email.

The post Delegation Challenge – Days 14-30 appeared first on Steve Pavlina.

Steve Pavlina

Steve Pavlina is an American self-help author, motivational speaker and entrepreneur. He is the author of the web site and the book Personal Development for Smart People.

You may also like...