What would happen if you stopped blaming yourself and started looking at your system?
You’ve got a brilliant idea for a side hustle. You’ve bought the domain, secured the social handles, told the world it’s coming. Then nothing. It’s not that you aren’t excited about the idea. You’ve always wanted to run your own business. A side hustle feels like a solid plan to get there. Still, nothing.
It makes no sense. You have no problem getting things done at work. Even hard things. That presentation? Done. The problem no-one else could solve? Sorted. Your boss is impressed. Your colleagues come to you when they need someone who delivers.
And yet, Saturday morning. Laptop open. Coffee ready. All the time in the world to work on the side hustle. You sit down. Nothing happens. The same project that’s been sitting there for months, maybe years. Still sitting there.
Same brain. Same person. Completely different results. How can that be?
You’re relying on motivation. Motivation is unreliable. Take a look at your system. There’s a flaw. Once you see it, everything is different.
Here’s 7 ways your system could be holding you back:
1. Clarity at work, chaos with your business
Your boss sends the brief. Clear deliverables. Specific requirements. Defined success metrics. You know exactly what ‘done’ looks like because someone else told you. Or you’ve been doing it long enough you just know.
Your side hustle? You must figure out what needs doing. What order to do it in. Whether you’re working on the right things. Set a standard for success. And know what ‘done’ looks like.
I used to open my laptop on Saturday mornings with ‘work on the business’ in my calendar. That was the plan. Work on what? Website copy? Email sequence? Social media content? All of it felt essential and none of it felt clear. The nagging voice in my head said, work on the income generating task. But which one was that?
The reality. At work, someone creates clarity for you. Your job role is clearly defined. You’ve been doing it long enough to know. With your side hustle, you must create it yourself. That’s not a small difference. It’s a completely different skill set.
What I tried. I wrote a long list of everything I ‘needed’ to do. Then I went back through and wrote down why each thing mattered. Next, I chose the three things that felt most important. I wrote a plan for each. Step by step.
The blind spot. I thought I was procrastinating. But I was overwhelmed by decision fatigue. Making lists and plans created temporary clarity. It helped for a few weeks. Then I was back to staring at the screen, overwhelmed again.
I couldn’t see the real problem. I kept generating clarity instead of building a system that created it automatically. Being a business owner means being the whole team – every role is yours, not just the one you’re good at.
2. Work deadlines are real, side hustle ones aren’t
Your manager schedules a meeting. Other people are waiting for your work. Miss the deadline and there are consequences for your reputation, your performance review, your credibility. The deadline is real because other people make it real.
Your side hustle launch date? You set it. It passes. Nothing happens. The only person who knows you missed it is you. No real consequences. You just reset it. Again. And again.
I used to put “LAUNCH” in my calendar like that would make it happen. Bold letters. All caps. This time it’s real. The date would come and go. I’d set a new one. Same thing. Eventually I stopped setting dates because I stopped believing them myself.
The reality. It’s not that you can’t do it. Or that you don’t want it enough. You need something that makes deadlines real instead of theoretical.
What I tried. Telling a friend and asking them to hold me accountable. They didn’t. My excuses sounded credible. They didn’t know how (or didn’t want) to challenge me.
I considered leaving my job – nothing motivates like no income, right? Too scary. I joined a group with a mentor instead. It worked. To a point.
The blind spot. I thought the problem was deadlines. It was accountability. Without external accountability, the deadlines stay theoretical. You need something that makes them real.
3. Your boss holds you accountable, but you can’t do it yourself
Weekly check-ins with your manager. Progress updates. Status reports. Someone is tracking whether you did what you said you’d do. That external accountability keeps you moving even when motivation dips.
Your side hustle? The only person checking if you worked on it is you. When you don’t, you just feel guilty. No one else cares. No one knows. No one’s tracking it. It’s completely optional. So, you opt out and feel guilty instead.
The reality. You’re brilliant at meeting external accountability. Self-accountability is a completely different skill set. It doesn’t work the way you think it should.
What I tried. Accountability partners that couldn’t keep me accountable. Weekly check-in calls where we’d share progress. Sounded great. Except when I hadn’t made progress, I’d avoid the call. Or show up and make excuses. Or stop scheduling them altogether because the guilt was worse than not doing the work.
The blind spot. You think successful entrepreneurs are just better at holding themselves accountable. They’re not. They’ve built external accountability into their infrastructure.
4. Work carries you; side hustles need you to generate momentum
Your workday has rhythm. Meetings create momentum. The calendar moves you from task to task. Colleagues need things from you. The environment signals ‘this is work time’. You don’t have to generate energy, the system carries you.
Your side hustle? You finish work exhausted. Collapse on the sofa. It’s your job to find the energy to open your laptop. Create the motivation to start. Generate the momentum from nothing. After a full day at work? Impossible.
The reality. At work you’re brilliant at execution within an existing system. Your side hustle doesn’t have a system yet. You’re trying to generate momentum in a vacuum.
What I tried. I used pep talks. Meditation exercises. A quick walk to ‘clear my head’. Rarely worked. I’d get frustrated with myself. Why can’t you just DO IT? You managed a full day at work, why can’t you manage an hour on the business?
Then I realised. It’s not the same. Work has natural rhythm and momentum. Side hustles don’t.
The blind spot. You’re comparing your execution abilities in completely different contexts and concluding something’s wrong with you. The comparison is unfair. At work, the system generates momentum. With your side hustle, you’re generating it yourself. That’s not a small difference.
5. Work needs employee infrastructure, side hustles entrepreneur infrastructure
Corporate execution systems are designed for employee work. They require external structure – bosses, teams, deadlines, consequences. Take away that external infrastructure and the whole system collapses.
Side hustles require completely different infrastructure. Internal structure. Self-generated clarity. Personal accountability. Momentum without external pressure. It’s not the same system with more willpower – it’s a different operating system entirely.
The reality. You’ve spent months (years?) forcing yourself to work within a system that was never designed for what you’re building.
What I tried. I kept trying to apply my day job system to my side hustle. Project plans. Status updates to myself. It felt ridiculous because there was no external structure holding it together. I couldn’t see that I was trying to run Windows on my Mac.
The blind spot. You think you need to try harder. You don’t. You need different infrastructure. No amount of willpower fixes a system that’s fundamentally wrong for what you’re building.
6. You think the problem is you. It isn’t
You look at your lack of progress. You look at how brilliant you are at work. The conclusion feels obvious. ‘I must not be disciplined enough’ or ‘I must not want it enough’ or ‘I’m just not cut out for this’.
So, you try harder. More motivation. Better morning routines. Stricter schedules. Your side hustle stays stuck.
The reality. You’re capable. You’re motivated. You’re just using the wrong infrastructure for the work you’re trying to do.
What I tried. I spent years thinking I was the problem. Reading books about discipline only to conclude that I hate the word. Following productivity gurus who made me feel crap. Trying to force myself to be different. Then I realised that I don’t need to be different. I need a different approach.
The blind spot. You can’t see that the system itself is wrong because you’re inside it. Once you see it, everything shifts. You’re not broken. Your system is. And systems can be rebuilt.
7. What changes when you stop trying harder and start building differently
My 1700-day run streak doesn’t work because I’m more disciplined than you. It works because I built infrastructure that makes running easier than not running. Same principle applies to side hustles that get off the ground.
You don’t need more willpower. You need systems that create clarity when there’s no boss defining it. Structure that generates accountability when no one else is checking. Rhythms that build momentum without external pressure.
Once you see the blind spot – that you’re using employee infrastructure for entrepreneur work – you can choose to build something different. Infrastructure designed for your life. Your energy patterns. Your constraints.
The reality. The solution isn’t willpower. It’s different infrastructure. Systems that create clarity without a boss. Structure that generates accountability without external pressure. Rhythms that build momentum designed for your life, your energy patterns, your constraints.
What this means for you. You don’t need more motivation. You don’t need to be more disciplined. You need infrastructure that works with your life, not against it. Once you build that, everything changes.
From excuses to action
Once you see the blind spot – that you’re using employee infrastructure for entrepreneur work – everything shifts. You stop blaming yourself. You stop trying harder within the wrong system. You start building different infrastructure instead.
When your infrastructure fits your actual work, the exhaustion stops. The guilt stops. The stuck feeling stops. You make progress without burning out. The side hustle that’s been sitting there for months, or years, finally starts moving. That’s what happened for me.
Struggling to spot what’s holding you back? Don’t have the mental space to figure out what’s draining your energy? Download this quick worksheet and see what it reveals.
