Interested in starting your own entrepreneurial journey in business development but unsure what to expect? Then read up on our interview with Jess Dewell, Managing Partner, Operations + Strategy of Red Direction, located in Kirkland, WA, USA.

What's your business, and who are your customers?

Forging a path is difficult and requires courage. For as long as I can remember, when describing what I was working on, people offered advice. Always. Even today! I quickly realized that most of the advice was invariably well-intentioned yet very specific to the experiences of the giver.

Wanting to show that I valued the shared information, I soon had a to-do list, so long completion was impossible. I always felt the timing was off, and I was behind, and my blindspots started not only showing up but getting in my way.

That was true from my earliest endeavors selling Girl Scout cookies in the 1980s and 1990s! After experiencing both failures and successes since then, I realized that entrepreneurs and business owners really wanted to know: the best path to achieving goals, what steps to take, and why they continually commit to actions that are associated with others’ success. All of which overlooks the most impactful part of the mix: your business strategy and prioritizing actions that move your company toward its most important goals.

Red Direction serves entrepreneurs and owners of small and medium businesses who want to clarify their path to success and build the map to get there. We are the red pointer on a compass aiming toward your true north. We show the right techniques and offer guidance to use this pointer to move in the direction you want to go with your business.

Tell us about yourself

I have a complicated relationship with linear time. One aspect comes from external expectations: you should be able to learn this or do that or complete a particular task by such-and-such date. Deadlines are self-inflicted and can be rationalized. True liberation happened when I realized that I couldn’t squeeze creativity and deep work into small chunks of time. I need at least 3-4 hours in a work session to create, consider, and make big decisions. Turns out, I’m not alone. Every year there is more research that comes out about how to become more creative and mindful (and they all involve less structure). My energy is my fuel, and recognizing that empowered me to challenge what I believed to be true about time, calendars, and due dates. We hear every day that to achieve everything we want, we just have to do more. More, more, and more!

Embracing the idea that there is a point of diminishing return relating to what is scheduled and what is possible — is, frankly, a difficult concept to comprehend. So… Shifting from: “How much can I fit in the time I have?” to: “What is the most important thing to be doing with my time right now?” …is a journey that requires room for trial and error, grace, and digging deep within oneself to keep going forward. Especially with regard to holding the vision for and leading a company. Those who are unable to shift fall into the 99 of 100 companies that are out of business within ten years. I am motivated to increase the number of businesses that have thrived for more than a decade.

What's your biggest accomplishment as a business owner?

All my failures are my biggest accomplishment. Through failures, I’ve learned more about who I am and who I still want to become, how I can be impactful and of service to others, and really, really clear on what I don’t like or want. There are two tools that I developed over the course of 24 years filled with experiences in building and growing thriving businesses that consistently deliver results. They are gifts that I have created and offer to you:

Present Retreat. The tool to build accountability for yourself and your business.

Here is a PDF that gives you ten questions for accountability and the Present Retreat™ framework.

LEAD Model for Better Decision-Making and Problem-Solving is an article that will help you identify when competing priorities exist and what to do about them.

What's one of the hardest things that come with being a business owner?

Knowing what is most important. There are fantastic structures, including Profit First, Traction, and the 12-week year to name a few, that provide repeatable processes necessary for every business. The real challenge is the needed additions to your chosen framework: the levers where you can increase or decrease revenue, how to implement, what to choose, and commitment to specific work practices.

What I’ve learned is how important the levers that drive my business are. I didn’t know what they were at first, and I was always guessing and unable to maximize effort. So what exactly are these “levers”? Specifically your unique selling proposition, the solution you offer your customers, and what you do best in the world.

Once you’ve found those levers, become familiar with them. So much so that they integrate into the way, you show up to choose what is most important. The starting point? Use your unique selling proposition, your solution to a customer’s problem, and what you are best at. Your weekly Present Retreat™ is a good time to put effort into developing, testing, and refining to know what is most important.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Choose a time each week, preferably the same day and time that is protected from interruptions. This time, your Present Retreat™ is for you to review your business, assess progress, make adjustments, and make decisions that relate to your current goals and overall business strategy.
  2. Have someone to hold you accountable. The resources I share here will get you started. Make sure it is someone who can challenge you to find your assumptions and help you lean into your strengths to navigate your business successfully over time.
  3. Be ruthless about staying true to your goals. Only ideas and collaborations that keep you focused on your goals are what you say YES to. Then, after your work is done, your self-care is done, and your personal priorities are done … that is when you determine: Is there time left to do more?

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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