The Difference Between Working In Your Business and On It
By Shawn Crabb, Crabb Digital Media & Design

If you’re a small business owner wearing all the hats—from product fulfillment and customer service to marketing and bookkeeping—it’s easy to fall into a daily cycle of checking off tasks, answering emails, and staying afloat. But if you’re spending the majority of your time doing that, you may be missing the bigger picture.

There’s a crucial difference between working in your business and working on your business. Understanding—and balancing—these two modes of operation can be the key to sustainable growth, long-term success, and even your personal well-being as a business owner.

Working In Your Business: The Technician’s Trap

Working in your business means you’re hands-on with the day-to-day tasks. You’re the one making the product, answering inquiries, shipping orders, updating social media, managing invoices, and doing customer follow-up. These are all essential operations that keep your business alive and moving.

You might be working in your business if you:

Can’t step away without operations halting
Spend your day reacting rather than planning
Rarely delegate because it’s “easier to do it yourself”
Are always busy but struggle to measure actual growth

There’s nothing wrong with this mode—it’s necessary. Especially in the early stages of business ownership, being involved is often unavoidable. But if you never rise above the technician level, you risk burnout, stagnation, or worse: building a job instead of a business.

Working On Your Business: The Visionary’s Role

Working on your business, however, involves stepping back and seeing the bigger picture. It’s where strategy, planning, and leadership happen. It’s about building systems so your business can run without your constant presence and making decisions that guide the company’s direction.

You’re working on your business when you:

Analyze metrics to make better marketing and sales decisions
Create repeatable systems and SOPs (Standard Operating Procedures)
Develop growth strategies (quarterly planning, hiring, scaling)
Focus on brand development, partnerships, and visibility
Invest in personal development or mentorship to grow as a leader

This work may feel less urgent—but it’s infinitely more important if your goal is to grow a business, not just keep one going.

The Trap: Why Many Entrepreneurs Stay “In”

The truth is, working in your business feels productive. It’s satisfying to check off boxes and feel busy. You may even feel a sense of control and accomplishment. But without taking time to zoom out, you risk staying stuck in the same cycle year after year.

Many business owners avoid working on their business because:

It requires slowing down to think strategically
They’re not sure what to do first
It can feel overwhelming or outside their comfort zone
There’s a belief that “no one can do it like I do”

The irony? Staying too busy prevents you from building the systems and structure that would free you to grow—and eventually, reclaim your time.

How to Shift from In to On

Here are a few ways to gradually shift into a more strategic role:

Schedule CEO Time Weekly
Block off 1–2 hours each week to step away from doing and spend time reflecting, planning, and reviewing your numbers.
Document Your Processes
Start writing down how you do repeatable tasks (e.g., onboarding clients, packaging orders). These will become your SOPs, making it easier to outsource or delegate in the future.
Outsource Low-Impact Tasks
Use platforms like Fiverr, Upwork, or hire a virtual assistant to handle things like data entry, social media scheduling, or customer inquiries.
Track Key Metrics
Numbers tell the truth. Begin reviewing weekly sales, email open rates, ad performance, or website traffic. Use this data to inform your next moves.
Reconnect with Your Vision
Ask yourself: What do I want this business to become in the next 1–3 years? Use that as a guiding light for all strategic decisions.

Why It Matters

Making the shift from being the doer of all things to becoming the strategic leader of your business isn’t a luxury—it’s a necessity if you want to grow without burning out. Businesses that scale successfully do so because their owners prioritize both execution and elevation.

You don’t need to abandon the day-to-day entirely. But you do need to protect time for strategy, systems, and leadership—the very things that will allow your business to thrive with or without your constant oversight.

So, the next time you find yourself buried in to-dos, ask:
Am I working in my business… or on it?

Your future self will thank you for knowing the difference.