7 lessons learned after 7 years in business

Jackie Colburn
7 min readMar 18, 2024


About seven years ago I started my own facilitation business and, in honor of that anniversary, I want to celebrate by sharing a few of my favorite learnings with the people who have supported me along the way.

Plus, some developmental psychologists have proposed theories that life stages occur in approximately seven-year intervals, so it feels like an auspicious time to reflect.

Regardless of whether or not it’s true, I hope you’ll find these insights and takeaways helpful whether you’re running your own business, or are simply navigating the ebbs and flows of life and work.

And thank you to all of you who have been there along the way — friends, collaborators, colleagues, clients, and the teams I have been so lucky to support with my work. Cheers to 7 years!

7 Lessons Learned After 7 Years in Business

1. Relationships matter, and great relationships are fueled by great work

When I started my facilitation practice, my network was my biggest asset. My business was built on the positive relationships I had fostered — from the people I’d worked with and for, the clients I’d helped, and my personal connections. This is likely in-part due to the fact that one of my core values is to always put humans first.

Today, I’m proud to say that I have many repeat clients who come to me time and time again for help. Here are the things I’ve learned are important:

  • Do the work you said you were going to do (it sounds simple, but value and trust come from fulfilling promises and producing good work)
  • Deliver the work on time, and manage expectations along the way
  • Treat people with kindness and respect
  • Practice active listening
  • Be candid but kind (I’m always honest when I share my observations while working with teams)

While doing great work is absolutely essential no matter your role, it’s also important to authentically invest in relationships beyond the occasional LinkedIn message. I make it a point to share blog posts and articles from peers and thought leaders. I’m not afraid to say the names of professionals in my circle amongst a group of people who are looking for referrals. And I make it a point to have coffee with people simply to stay in touch and connected, because you never know where it might lead. And here’s the funny thing about doing this: other people start returning the energy, sharing my content, and saying my name in the right rooms. This virtuous circle has been instrumental in the growth and success of my business.

2. Expertise is important

Trust me, I understand the temptation to say “yes” to a lot of things that might not be your area of passion or true expertise. I’m endlessly fascinated by many topics and am fortunate to be able to say that I am good at many things. It can be hard to commit and focus because you may feel like you’re leaving something on the table. But clarifying your unique value goes a long way at helping you hone your expertise and be known for it.

My specialization in facilitation with deep expertise in digital product and technology helps people understand the value I can provide and ensures that they’ll be better able to determine when they will benefit from working with me. When thinking about the work you want to be doing, don’t be shy about telling people about why you’re great at that work: from the way that you share success stories or case studies, to the content or writing you produce, stay true to your distinct area of focus and expertise.

3. Learning and adaptation are necessary

No matter which industry you work in, continued education and resilience are critical to staying relevant. Do you have professional development circles you can join? Or a list of thought leaders you can follow to stay on top of trends and advancements? How about conferences you can attend, or virtual workshops you might participate in?

In 2020, I had to figure out how to transition from in-person workshops — which was almost the entirety of my business — to remote workshops. To do this successfully, I needed to learn a new set of tools, like becoming a pro at virtual facilitation software. Without a commitment to learning, I could have easily spun out and fallen behind. But I didn’t freeze and, as a result, my business actually grew during the pandemic because I was so committed to making remote workshops effective and enjoyable.

At the end of the day, there’s only so much you can be prepared for, so make space for learning in a capacity that makes sense for you. And never stop being curious about different and new ways to evolve the work you do.

4. Perspective is an asset

As an outside consultant, I have the unique advantage of being more objective when it comes to evaluating the challenge ahead of the teams I work with. I also bring knowledge from working with organizations in many industries.

My fresh perspective and outsider’s viewpoint provides insight and helps to cultivate ideas that may be overlooked by internal teams who are too close to the problem.

In my facilitation work, I often drop into the thick of internal team dynamics and can be a voice of reason when people are too immersed in the day-to-day. My insight helps teams move more easily toward ideas that may have otherwise been overlooked or not considered at all because they’re too caught up in dynamics that are keeping them from moving forward.

So, remember that you bring a unique and fresh perspective to any team or client you work with — don’t be afraid to own it!

5. Challenges will happen — it doesn’t mean you can’t overcome them

Changes and challenges are inevitable. I know it. You know it. But knowing it doesn’t mean it’s easy to navigate the unpredictability of doing business (and living) in the modern world. I bring this point to surface simply to remind you that you CAN survive the challenges that arise.

It might be a little uncomfortable or take longer than you’d like, but with patience, openness, and opportunistic thinking, there’s usually a light at the end of the tunnel.

When the pandemic hit, my entire business could have folded. It was all based on in-person workshops! But I quickly learned virtual tools and how to implement them for remote sessions. As I mentioned earlier, jumping this hurtle actually helped me grow my business during a time when things could have easily gone the other direction.

During this same timeframe, I had planned to be on the road running Design Sprint bootcamps with my friends John Zeratsky and Jake Knapp. Needless to say, I was sad I didn’t get to see this come to fruition. However, we quickly pivoted. Instead of feeling defeated, we engaged in a month-long research project to figure out how to help people quickly shift their way of working. The result was our Remote Sprint Guide, and it’s a tool used by many to this day!

My point is, when you hit a wall, suit up in your climbing gear and find a way around it.

6. Staying the course takes continuous recommitment

Seven years is a long time to do anything with consistency, and getting here has taken continuous recommitment and focus. Making it to this mile marker is not insignificant, hence this post cheering myself on!

As with any long journey or relationship, there are tiring moments, and times of frustration and doubt. External challenges are inevitable, but the internal stuff can be especially difficult — those moments that make you want to get off course in the midst of a long race and head for home. The thing about difficult moments that I’ve learned in seven years running my business is that it’s about staying steady through them.

I’ve found that the best recipe for staying the course to be:

  • Acknowledge potential lessons and learnings that may be present in difficult moments
  • Talk to others for supportive counsel, affirmations, and help (see point #1 about the importance of relationships)
  • Give yourself permission to have other avenues to fill you up outside of your main gig and put those front and center to keep perspective
  • Remember not to make big decisions when you’re in a difficult moment — let the wave rise and fall, and see how you feel on the other side

7. Define and design a business you actually want to run

Ok, so this one is likely only relevant to those of you who are running your own businesses, but I’d argue that even if you’re working inside an org, some of these points may ring true for you.

I’ve met too many business owners who seem to begrudgingly run their businesses. Sometimes it’s a matter of not delegating the right things, and sometimes it’s losing sight of why they started a business in the first place.

Whether you’re considering starting a business or are already several years in, I highly encourage you to always stay oriented to your purpose. Clearly define your goals, then ask at every turn if your actions and decisions are in support of it.

There have been plenty of moments of exploration for me along my seven-year journey as a solopreneur — do I want to scale, or hire employees, or focus on a different specialty? But I’ve considered these things cautiously and deliberately because I don’t want to accidentally begrudge my life, or make decisions based on societal pressures or momentary whims.

You get to decide what success looks for you, and that might be different from what you’ve been told to want. Trust your instincts and stay true to them!

To Round It Out

My hope is that practicing any of these habits will support you in building a professional life that you love. After seven years in business, I can honestly say that the relationships and peers I’ve cultivated have been one of the most instrumental parts in walking this road. So cheers to this path, and seven more years of learnings!

What else would you add to this list? Let me know the lessons you’ve learned in running your own business by leaving a comment, and maybe even a few claps to let me know if you liked this topic!



Jackie Colburn

Weekly resources for facilitators and leaders. Learn tips and methods to run better workshops, accelerate teams and uncover new ideas. www.jackiecolburn.com