When Entrepreneur Productivity Hacks Don’t Work for You

Entrepreneur Productivity Hacks

I ran across a Copyhackers blog post about throwing what you’re “supposed” to do as a freelancer out the window. It resonated with me when I started my business, and it resonates with me still.

I feel like I’ve tried every productivity hack in the world, and some work OK, but most just don’t. I’ve spent years learning how I work best and trying different ways of managing my work, structuring my days, and coming to accept that there is no one-size-fits-all structure.

Lessons Learned

Since going out on my own, I’ve tried all sorts of things to make sure I get work done, have time for my friends and family, and make the most of my days (but leave plenty of relaxing time). In the process of experimenting, I’ve learned some things about myself.

  • A rigid schedule DOES NOT work for me.
  • I need what I call a “flexible structure” in planning my work.
  • I need to be mindful. Listen to my brain and body. Adapt and adjust.
  • I’m going to procrastinate…it is what it is.
  • I’m most successful when I make small changes.

My Schedule is Mine

A lot of the fancy entrepreneur blogs and productivity experts say that people who work for themselves need to set a schedule and stick to it. I tried it. It didn’t work for me. I tried working 9 to 5, the schedule I had at my previous job, and it just didn’t go well. I tried 10-6 to see if starting later would help my night-owl brain. Again, that just didn’t do it for me.

Next, I tried no schedule. No expectations for myself about when I’d work—except for pre-scheduled meetings, of course. I’d work when I wanted to and not work when I didn’t want to. This sounds like it could be a disaster, but when you actually enjoy your work, it goes OK. So this approach did, in fact, go OK. I got work done. Sometimes I would crush the day and do 12 hours work. And then I’d have two days where I’d just sleep and lounge around. That just wasn’t sustainable.

Turns out…I needed something in between strict structure and laissez faire.

I now focus on routine, not structure. I tend to work from 10 or 11 until late afternoon and then a few more hours after dinner. Specific times depend on my meeting schedule, how long my workout is, when I hit my afternoon wall, and if I have any social engagements in the evening. This flexibility works for me, in part, because I don’t have a significant other or a family to care for.

I still have a lot of variety in how much I work each day. Again, it depends on what deadlines I have and the other factors mentioned above, but it also depends heavily on how my brain feels and how nice (or not) the weather is. If the weather is gorgeous and I want to go for a bike ride, I’m probably going to go for that bike ride. I can do that at 1 in the afternoon because, well, I can. But it means I’ll probably be working until 11 or midnight. And that’s OK with me!

I work a lot of weekends. That sounds weird to people but I love working on weekends. There are no meetings (that’s one of my unbreakable rules), email volume slows down, and I can just get work done. I love it. I try to take a weekday off most weeks, but that doesn’t always happen. And yet I don’t feel burnt out—because I have complete freedom over when I work and the type of work I do. The so-called gurus on this topic would scold me, but it works for me and that’s what matters.

The ultimate schedule flexibility is worth it. I love being able to pop out and take the dog for a run or lying down for a nap to reboot in the middle of the day. I have enough discipline (OK, I have a system in place that keeps me disciplined) that I know I’ll get my work done. And again, when it’s work you enjoy, it’s not hard to “make” yourself sit at the computer to do it.

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I will pause here to point out that I know how lucky I am to be able to have this kind of flexibility. I sit on a pile of privilege and am very aware of that fact. There are so many things in my life that lined up just right for me to have this kind of career, and I’m thankful every day.

Going With My Brain Flow

As you learned in the last section, I’m not exactly strict in my working days and hours…quite the opposite. As someone who has struggled with mental illness my whole life, I have had to learn to adapt to the whims of my brain chemicals. There are days when I just can’t focus. And I’ve had to become OK with that. Forcing myself to sit at the computer and stare at a blank page isn’t beneficial for anyone. I’ve learned to walk away (which wasn’t easy).

When my brain just can’t, I go easy on myself. I go for a walk, find a non-brain project to do around the house, or take a nap. I may get back to my computer that day, but I may not. And because I have ultimate flexibility, that’s OK.

Some days I feel like writing, other days I don’t. I try to do the work that fits best with what I’m feeling and where I think I can make the most progress. Some days I’m all about writing. Other days, I just want to build something—in WordPress, ClickFunnels, or whatever other tool at my disposal.

Being flexible and not forcing myself into trying to work on something when I can’t focus has been a huge help in improving the quality of my deliverables.

The “Hacks” that Do Work for Me

As I said, I’ve tried so many of the productivity hacks for entrepreneurs and people who work from home. It’s a numbers game. Some of them are bound to stick, right?

Most didn’t, but some of them did.

I have a dedicated workspace. This turned out to be very important for me. I love working in my recliner with my laptop on my lap and something mundane on the TV. But that’s not an ideal working environment for everything I do. I still work in my recliner, but I usually save that spot for admin work and working on my own business. For client work, I go to my office. And by office, I mean office/gym/library. It’s a room in my house with my weights, resistance bands, and hundreds of books. It also has a desk with my laptop, notebooks, and a second monitor. I got myself a comfy leather chair and now do most of my work (including writing this) here.

My brain works best with checklists. I’m always making lists, but it took me a long time to realize that they actually help me get stuff done. I’ve used checklists to rework my habits, lose weight, complete house projects, and more. I now have checklists for my work, my personal tasks…pretty much everything. My brain moves fast and it’s easy for me to forget to do something. When it’s on my list, I know it’ll get done.

Planning my work is hard for me. I want to do all the things. But I know I can’t. So I plan my work by the week. Each week (run my weeks Monday – Sunday), my virtual assistant (VA) pulls my work from clients’ various project management systems and puts them in my Asana. She organized the work by day so it’s all in a handy checklist for me. I know which work to do in what order, and there’s an approximate day assigned to it. The work may or may not happen on the planned day, but most of the time, I can get the week’s work done.

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I learned long ago that I need to plan my day. It never goes exactly to plan, but the act of planning is very important. If I don’t plan my day, I’ll end up working on low-value, non-urgent items instead of what I should be doing. I’m a night owl. Always have been; probably always will be. So I plan my next day each night before I shut down. This small step at the end of each day (I say day, but it’s usually 10 or 11 p.m.) means that when I sit down in the morning (again, probably more like noon), I don’t have to think about what to do. I can just do it. And per my previous comments about planning by the week and being flexible with my brain, I leave wiggle room for adjustments based on mood and unexpected pop-ups.

My mind moves very quickly. I’ve found that I can help myself by documenting everything as it pops into my brain. If I remember something I need to do or have an idea, I write it down or put it in my phone. Then every few days, I go through and get those thoughts documented where they need to go (a checklist, Asana, an email). I hate that “am I forgetting something?” feeling. By having a system that helps me remember what I need to remember, I can quickly swat away that feeling and move on with what I’m doing.

Embracing Procrastination

I’ve built my life on a crumbling foundation of procrastination. I’ve always been a procrastinator…and likely always will be.

I’ve felt powerless to change my procrastination tendencies (I’ve never had consequences, so why would I change?). Instead, I’ve changed everything surrounding my inevitable procrastination.

The worst part of procrastination is the shame spiral. For me, I feel guilt and shame when I’m procrastinating. I get anxious and have trouble focusing. And that makes it hard to start the work. It’s a vicious cycle.

So instead of letting myself spiral, I’ve changed my mindset. Now I plan for the procrastination and accept it as part of my work style.

Now, when I’m procrastinating, I don’t sit here feeling guilty and trying to force myself to go against my natural procrastination tendencies. Instead, I use  that time to do other, less anxiety-inducing work.

Then, when it’s time to hit the ground running on the project I procrastinated, I make it happen, like I always do, but without the pre-project anxiety spiral.

It’s not a perfect system, but I’ve come to accept that I do really good work when I procrastinate. Now I just avoid the negative side effects leading up to it.

Experiment, Test, Revise, Repeat

I’ve tried to and failed at completely revamping my working style. Big, drastic changes just don’t work for me (or anyone, I’m guessing). I shift small things and do so over time—not all at once. That’s how improvements stick.

I go into every adjustment as an experiment, which makes it OK to “fail.” When I try something I think might help me work better and it doesn’t work, that’s OK. I will try the next thing. For example, I saw somewhere that people write out their day on paper, by the hour. I figured that would fit well into my nightly planning for the next day. I tried it. It went very poorly. I didn’t see any benefits and I actually found myself resenting the hour-by-hour structure. So I stopped! Now I focus on the things I need or want to get done, and do them without the rigidity.

Entrepreneurship is a Journey

I continue to say that the only thing that would send me back to a “real” job at this point is if the health insurance landscape changed drastically and I needed a employer-funded plan. (That’s a whole different topic.)

I’m still loving the journey I’m on. While it hasn’t been hiccup-free, it’s a work lifestyle I can’t imagine giving up.

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