Rungs and Ladders Part 2 - Figure Out Own Ladder (24/30)

I'm writing 30 posts in 30 days. This is number 24.

Previously, I went into deep details about my own situation and what options I can take to move to the next level in the conceptual ladder that is my software business. I also mentioned the Rob’s stair-steps and Nathan’s ladders metaphors in the same post as they serve as useful rail guards for my own thinking in this matter. There are a couple issues when using ladders and stair-steps as thinking metaphors I wanted to cover but didn’t. So, this post is a deeper dive into those issues.

Definite Roadmaps by Other People Sell Comfort. Not Prescription

My current ladder is a bit weird. It doesn’t neatly fall under services business nor is it productized services. It has characteristics of both. and has characteristics of neither. It has the potential to become a product business, I suppose. Or it serves as a launchpad for me to move into a product business that I have to start from scratch. The truth is, nobody knows for sure. And either case is possible.

This brings me to the first point about using such metaphors: they are there to provide some direction, but you cannot follow them too blindly.

Yes, directionally, some steps naturally make sense together to form a conceptual ladder. Yes, some steps do make it easier to go to higher steps. But no, there’s nothing written in stone that some steps are necessary or sufficient to get you to those higher steps.

Even if I were to abandon metaphors and actively searched for definite roadmaps, anybody who claimed that their way is the only way is not selling you advice. They are selling you a religion. No prescription is ever possible given the unbounded nature of the thing that we call business.

We need to perform experimentation with some thoughtfulness and constantly revise the plans when new information emerges. Not planning at all and working haphazardly without thought is irresponsible. I am guilty of this in certain past instances. Not being responsive and adapting your plans when new information emerges is just as irresponsible. I’m also guilty of this sin of inflexibility in certain past instances.

Making fewer such mistakes going forward would be a key consideration as I seek to go after a 1 million ARR software business.

Transition is the Bottleneck

I also mentioned in Part 1 how I already have a ramen-profitable, breakeven profitable business going. Taking the metaphor of stair-steps further, I am now at the point of gingerly lifting one leg up in the air, trying to plant it in the next higher step whilst balancing myself on the one standing leg in the current step, without falling down.

That’s what I would call a transition. Some transitions are easier. Others are harder. A transition is easier if the next step isn’t that much higher than the current step in terms of difficulty. So choose the next step wisely.

On the other hand, if I were to have weak legs, it would be difficult to balance on one leg no matter how easy the next step is. So strengthening my legs is crucial as well.

For myself, definitely it’s choosing both emphatically. I need to choose the next step wisely and push for it relentlessly, while making sure I am strong enough to balance myself on one leg.

You May Have to Figure Out Your Own Ladder and Own Steps

I wish someone would write me an exact formula to make transitions and detailed roadmap of my path to 1 million ARR, but that’s never going to happen. No two successful businesses are exactly the same. At the very least, what anyone who wants to do is to be completely honest and list out exactly where you are at and where you want to go like I did in Part 1.

Of course, I don’t advocate ignoring all prior art. While sometimes, you cannot follow exactly what appears to be a common pattern used by other people, that doesn’t mean the common patterns are completely useless. This is the special snowflake fallacy. And just because other people follow some patterns doesn’t mean it will definitely work for you. This is the false analogy fallacy.

I advocate being mindful of falling into either fallacies.

So What Now?

Experiment. List out possible paths. Write down your plans and ideas no matter how sketchy they are — I use a physical notebook for this. Review regularly upon receiving new feedback. Adopt different personas for thinking and executing.

Are you like me when sometimes you can give better (as in more rational and more compassionate) advice to your own friends for their situations than for yourself? Then pretend you are your friend.

Analyze your situation as if it were a good friend whom you always give good advice that balances the need for rational analysis and compassionate understanding of their unique preferences.

Then, turn your mindspace around and be a blindly compliant worker executing those plans. Report any feedback based on actions. Now, switch back to the mindspace of being the kind, rational advisor. Review the plans based on feedback from the compliant worker. Adjust the plans accordingly. Switch again to the worker mindspace and execute again. Repeat as needed.

At least that’s what I am trying to do now.