I am Jason Scott Montoya, and I’ve been freelancing full-time since early 2014. I have been working with small business owners to grow themselves and their income. I also work with small business clients to build virtual teams of freelancers, sometimes utilizing the talented freelancers at FreeUp.
As my freelancing journey progressed, I applied the lessons learned and systems created from my prior seven-year journey as a marketing firm owner. I became so successful that other freelancers began buying me lunch asking for tips and guidance on how they, too, could flourish as career freelancers.
Now I have another book coming out — The Jump: From Chaos to Clarity For Your Striving Small Business.
As a fifth-generation entrepreneur, I have experienced small business ownership from every angle. I ran a marketing company and faced a litany of challenges running the business. After this, however, it was my freelancing journey that gave me a real front row seat to this entrepreneurial path working with numerous business owners.
It was at this point that I knew and felt what it was like to be on the other side of myself. And it gave me a clear picture of both the positive and negative dynamics of it all.
Many of the things I learned and the challenges I overcame were ones that my entrepreneurial clients were also facing. My desire to download my insights and stories to help them accelerate their journeys was therefore also a way for this book to act as a letter to my young self. I share in The Jump what I wish was shared with me as I struggled to make the business work and struggled with doubts about whether I’d ever make it out of the company alive.
While the book is valuable to folks across the wide spectrum of business entrepreneurship, this book is specifically aimed at striving small business owners who feel stuck.
Often, struggling entrepreneurs hit a revenue number and for several years can’t rise above this artificial ceiling. The days, weeks, and months feel like that Bill Murray movie, Groundhog Day, where every day feels like a repeat of the day before. It’s like they’re starting over, facing the same challenges, and dealing with the same negative consequences of their mixed decisions over and over again.
These entrepreneurs are striving to succeed, but at the same time wonder if they should keep going. They’re daydreaming about the future and freedom they once believed their business could give them. Faced with an existential crisis, however, they’re trapped in a self-made prison — they have no realistic way out of that endless cycle of thought: Keep on or shut down?
Broken and beaten, I offer them an answer. It’s not an easy one, but it’s the principles that will, when fully embraced, give them a pathway to the freedom they’ve sought but so far failed to achieve.
Often, when I get into work with my small business clients, it’s filled with the chaos of people not having clarity on what their roles are in the business. Some are owners who don’t know where they’re leading the company, so they are telling their troops to go in a variety of different directions. Others are vendors who are entangled in the business mess and getting caught up in the drama of this craziness. Still, others are clients who wonder what’s really going on and question whether they have made the right decisions.
Chaos can be defined in this context as the random management of a business that leads to broken promises and a wake of relational wreckage. More formally, I label chaos with the phrase, Rogue Action Management (RAM). RAM-ming things means not capturing ideas, not planning projects, failing to execute on planned ideas, dropping the ball on maintaining what matters, and never taking the time to audit and improve what’s going on.
Order is when business owners have captured this energy of activity into a focused and intentional outcome. They’ve got systems to capture ideas, plan them out, execute them excellently, keep them alive as long as they’re relevant, and regularly improve everything so it’s generating the outcome they’ve clearly articulated. Order is built on intentionality and sustained with discipline.
A chaotic organization can only grow as far as the business owner can will it forward. But, the herculean effort is wearying, so they burn out and the business regresses. When they’re rejuvenated, they do it again. Rinse and repeat. Eventually, it stops working altogether, and they never get past this negative cycle because they tend to give up. As much as they might resist it, owners must embrace the structure and face themselves to get past this seemingly impossible milestone.
When it comes to successfully scaling a small business, the person steering the ship is critical. The crux of scaling up a business is leveling up the captain of the ship. The founder and leader of a business is the one setting the example and pioneering for the team. This person is also the one deciding the vision, mission, purpose and values of the organization, which determine if the company is built on a sandy foundation or bedrock. When the storms come, or the desire to scale up is strong, it’s grounded business that’s needed — not just to survive, but to thrive.
With a strong leader and a solid foundation, the team and bullet-proof systems come into the picture. Scaling the business requires help from others. No one can do it alone. The systems, including people, processes, and resources, allow everyone to lean into the clarity of the company’s direction, while also giving freedom so they can move things towards the end game.
And it’s the people who are the future of the business. How well we equip and train them to succeed will determine how far they can build on the solid business foundation that the small business owners have established. At the end of the day, the heart of entrepreneurship is about mentoring others who will then disciple the next group. It starts with one and slowly and systematically replicates over time across countless people.
None of this happens if the captain steering the ship is a poor leader or lacking in character. And a great leader on a sandy foundation won’t build a great business.
Small companies will often get into chaos — it’s the natural direction of things. And while it would be best to prevent this and plan the business, departments, and projects before launching things, it doesn’t always happen. And we need a way to capture that chaos and morph it into a container we can control, or at least influence.
In The Jump, I mention a 5-step process for transforming a business into a well-oiled machine. Here’s how it unfolds.
What can you do to quickly reduce expenses and generate more income? What can you easily do to generate leads or increase conversion rates? The goal here is to buy us time so we have more runway to work on important medium and long-term campaigns.
Stop doing anything that is not contributing to moving the business forward. Consolidate efforts that are overlapping or unnecessarily segmented. The goal here is to get focused on what matters and eliminate everything else. For one client, we consolidated almost 800 blog posts into 150 evergreen ones. Our organic traffic and contact collection are way higher now. Often, less can be more.
Once we’ve pulled back from our over-committed context by shrinking what we’re driving, we can look at what we’ve simplified and take action on ways to improve things for the better. We simplify everything beforehand so our effort here is also as minimal as possible. The goal here is to figure out how we work smarter and do things more effectively.
As we’re getting focused and organized, getting things simplified and improved, we will naturally see gaps in our campaign. We want to find these gaps, and fill them to accomplish what our current efforts are focused on (no unrelated shiny objects here). Think of these as potholes on an existing road that need filling so the car can have a smooth ride and not get damaged in the process.
By now, we’ve gotten a handle on our business and we want to keep it that way. At this stage, we make sure we have a system of processes and people to sustain what we’ve done while also introducing new things in a methodical and integrated way. The goal here is to establish a habitual cadence to ensure things continue in an orderly way and don’t fall back into chaos. Slowly and surely, the business will grow and the ongoing momentum will take hold and facilitate the scale we’ve likely been seeking.
This is the process from chaos to order and it’ll serve you well each time you need it.
While we small business owners generally want to follow the order of this process, we’ll likely want or need to work on multiple phases at one time. Use this process as a guide, but shift it to match your context so it generates cash and grows the long-term benefits you need to sustain the business. Don’t skip stages because you’re uninterested.
If you feel like you are stuck or trapped in your small business, it’s time to seriously reflect on why you got into entrepreneurship in the first place. Through this exploration, you’ll want to ask yourself what type of business you could get excited about to the point where you’re willing to fully commit and make it work.
If it means you need to shift the direction of your current business, do it. If it means you need to change your business dramatically or start a new one altogether, seriously consider the change. Stuck small business owners don’t go anywhere but in circles, and I’d hate for that to happen to you for the next year or decade.
The Jump: From Chaos To Clarity For Your Striving Small Business is available on Amazon. When you purchase the physical copy, you get the Kindle edition for free.
To learn more about the book, visit this page for the book on my website. I’ve also got the following freebies:
You can also check out and subscribe to my blog where I share stories and systems to live better and work smarter.
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