Getting better at managing myself

I had about 30-40 sticky notes on my desk.

22 web browser windows open on my computer (each with 5+ tabs).

Texts to myself, voice notes, journal entries, Notion, Google Docs.

I have a lot of ideas …

And I’m diligent about writing them down (or recording a voice note).

I thought I was also fairly proficient at keeping my thoughts organized.

And getting the actionable ones done.

But running a startup as a solopreneur has proven to be more than my old system can handle.

The ideas keep coming, but I’m failing at the organization and execution stages.

There are a hundred different things I could work on, but where to start? Which task should I prioritize first? What will have the biggest impact?

It got to the point recently that I started to avoid thinking about work, sitting at my desk, or opening my computer because I knew I’d be met with an avalanche of unfinished tasks.

I even pushed new ideas out of my mind because I knew they would just be added to the top of an already insurmountable mountain of unfinished tasks.

That’s when I realized I needed to get better at managing myself and my business.

Transitioning from employee to entrepreneur

When I was working a W2 job, I relied on the systems that were already set up by the company.

They told me when/what/how to work. I just had to follow the instructions I received from:

1. My manager: another human responsible for managing me

2. My coworkers: veterans to learn from, emulate, and ask for advice

3. Training: documentation and instruction on how to do my job

4. Specialized role: clearly defined responsibilities and goals for my job title

5. Other company systems: pre-configured software tools, working hours, mandatory meetings, playbooks, scripts, templates

They made it obvious what I should be doing at any given time as an employee of a larger company.

Now that I’m a solopreneur, it’s much less obvious.

Failing to manage myself as a solopreneur

Now that I’m running Break Into Tech Sales on my own, I don't have management systems already set up for me. No manager/coworkers. No training. And my role isn’t specialized.

I’m my own manager. Teaching myself as I go along. And I wear every hat.

In the early stages, my lack of self-management wasn’t apparent.

I was mostly brainstorming, doing research, and coming up with ideas for marketing, product development, and monetization. The only system I needed was a journal for notes.

But now that I have clients, partners, and contractors.

Scheduled calls and project deadlines.

Expenses and revenue.

It’s a lot, and the workload continues to increase as the business grows.

At first, I was relying on sticky notes on my physical desktop, browser windows left open on my computer, and ideas in my head.

I knew I’d reached the limit of my old system when I had so many sticky notes I couldn’t move my mouse and so many open windows my computer was freezing.

It was also taking a toll on my mental health. I was struggling to separate myself from the work and “shut off.” Even when I stood up from my desk and closed my computer, work thoughts continued to cycle in my head.

And I just wasn’t getting things done. I would start a task, then get distracted by a notification, email, scheduled call, or another new idea. I was feeling overwhelmed and unsure of what to focus on at any given time.

I didn’t want to give up on the work. I just needed to find a better way to work (which wasn’t clear to me at first, but it is now).

Reasons why my old self-management system wasn’t working

1. No prioritization: How do I know what to work on first? Next? Which tasks am I de-prioritizing for now?

2. No scheduling: When do I work? Scheduled calls are the only events on my calendar. Should I block out time for tasks?

3. No organization: A standardized task management system with tags, folders, groups, themes, stages, etc.

4. No centralization: One central place to see everything I have going on.

5. No impact calculus: Which task will make the biggest impact for the least effort? Which business objective are we measuring impact for?

6. No work-life separation: Every time I look at my desk at home, I see all the sticky notes. When I open my laptop, I see all the windows. My brain keeps thinking about work stuff outside of work time.

There are probably more reasons than just those.

But it’s a list to start with.

These will be the minimum requirements for my new operating system.

Exploring options for a new self-management system

My first thought was that I needed scrum, agile, kanban, or something like that.

Then I remembered my brother telling me about how he started using the Getting Things Done methodology.

And my girlfriend told me about August Bradley who makes YouTube videos about setting up your “life operating system” in Notion.

I’m still researching these systems/methodologies and figuring out which one will work for me.

At a high level, I think I need to get better at two types of personal management:

• Task management: what are the things I need to do and how do I organize them?

• Time management: how do I use my time to get those things done?

I also need to delegate more.

There aren’t enough hours in the day for me to get everything done on my own.

So how can I find good/cheap contractors and hand off tasks/projects that they can complete for me?

In some cases, I can use SaaS or AI instead of human contractors.

Asking for advice

I know some of you who follow this newsletter are excellent operators, entrepreneurs, and hyper-productive people …

What systems do you use for task management?

For time management?

Do you outsource some of your work to contractors/AI?

Any other advice for me?

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