Reflections: Starting My Business

Transitioning from Employee to Business Owner

Choosing to start a business is a scary & exciting venture. A transition filled with unknowns, stressors, courage & fortitude. There is a level of leadership that no one can truly prepare you for.

I’ve been reflecting on my own business journey as I initiate another transition. There is much I’ve learned & continue to about myself as a result of having started a business. Today in this post, I want to share a few lessons with the hope there may be something here that resonates for you and a current transition you’re facing.

If you’re in this transition, take heart. Know you’re not alone.


In 2012, I felt it was time to start the business I’d always dreamed of. At that time, I’d been coaching & consulting within my organization for close to eight years. My intention was to support leaders across many industries. I had a dream of being my own boss with the creative freedom to design & deliver services in ways that felt authentic and effective.

I’d always sensed I’d have my own business, some day. I just had no idea what that would be. When I began my professional development as a coach and leadership consultant, the dots started to connect, and the vision began to take shape.

With solid Capricorn energies, I naturally crafted a plan. So, in 2012 when I opened my business, I developed a two-year plan where I would continue to work part time in my job and start to branch out to develop my business.

Having a blooming partnership with another company, I naturally started there. This grew, almost to the exclusion of my own business. There came a choice point at the end of my two-year plan. That was to work predominantly with them as I left my organizational role. I said yes. Without hesitation.

This was a good choice & filled with excitement. However, I failed to pause and check-in with my original dream. My company’s mission, my seed vision and my values. This was one of many experiences over the years where I’d learn this important lesson.

Lesson number one

Value time to pause, reflect and choose. 

Before any decision in business (and well in life) it’s important to pause. To take the time to reflect and check-in with yourself. Revisit your vision, mission & values. If you’re not clear on these, then this may be your first step if you’re transitioning into your new business. Checking in might reveal that the decision you’re about to make aligns, doesn’t or maybe you discover that your vision is shifting.

Get Clear

Get clear on What’s Ending

Whether you’ve lost a job or have chosen to leave a job, take some time to be clear on the W5 (Who, What, Where, When & Why) of this ending.

  • What has ended? (Your love of the work? or maybe Your ability to stay in the work?) 
  • What will you be losing/letting go? (e.g. title, secure income, daily routine, clear purpose)
  • Who else in your life will be experiencing an ending & loss? (e.g. family’s ability to count on your schedule, routine & financial support)

Make room for the emotions of grief.

Whether the choice to end what was your work your own or maybe the result of another, there will be grief emotions that need to be processed. I totally under-estimated this. I’d worked my entire life for an organization from the age of 16. As much as the choice to leave “the job” was my own, I was unprepared for the emotional landscape that unfolded for honestly a couple of years after leaving. The time frame was longer I believe because I didn’t make room to process these consciously. And like so many, I chose to travel this part of my transition alone.

Once you’ve welcomed the endings phase, then, begin to draft out the attitudinal & philosophical blueprint.

Write out your vision, mission & values.

I’ve found journalling to be an important companion. Allow yourself to wonder & wander around with your thoughts, on paper or on the screen. Often our heads get full with ideas, or we feel we’re clear when we’re not. Practically this can look like struggling with decision making, procrastination, feeling stuck.

Start with you. There are interesting threads between our personal principles (vision, mission & values) and those of our business. Many debate the validity and best approach to this. In my own experience it’s been important to begin with me. As a solo-preneur, one who activated my own transition, it’s been important to develop clarity here. Then, to focus my attention on those who I am serving. Clients guide the framework, process and approach, based on what they are seeking. And, in the absence of the personal clarity, it becomes challenging to forge ahead & cultivate the courage and fortitude inevitably required.

Lesson number two

Develop a plan for your business and your days.

Equally important to your attitudinal & philosophical blueprint is the practical nuts & bolts.

Yep. How many people advised me to develop a business plan? And well, I didn’t. I thought I could wing it. I knew who I wanted to serve & how I wanted to do this and in fact was already doing so with another company. I didn’t take the time to map out my own business plan. Fast forward many years and this is one do-over I would highly recommend. You see the process of developing a business plan is a good one. Honestly it will un-earth things you can’t even imagine you need to contemplate & consider. Even if you’re a solopreneur like me.

Second, have a daily plan, a schedule, a routine. This I’ve learned is mission critical. Yes, as entrepreneurs we live for freedom, freedom to create, to service & develop our business in ways that feel authentic for us. And, having a minimum specification to your daily schedule is a life saver. You’ll be surprised how much time can evaporate.

Transitions are by their nature unclear, sometimes chaotic and lack stability.

Investing time structuring your business plan & daily routine will help provide a place to land when your emotions take over and you feel lost in the fog.

Lesson number three

Be kind to yourself & Be you.

Take it easy. Don’t expect to slide into your business goals effortlessly. It takes time, work, experimentation, re-dos, un-dos and everything in between. Along the way you may discover some deep-seated threads of self-judgement taking hold. This requires a level of self-kindness I actually do not have the words for. Be flexible. Gently engage your self-doubt and judgements. They will emerge. If you resist them, well, they just get bigger. Trust me.

Be you! Resist the call to follow another’s path so much that you’re trying to be like another. The world needs you & what you’ve come here to share. Learn from others and stay true to who you are.

“Be yourself; everyone else is already taken.”

Oscar Wilde

Lesson number four

Get help. Learn, Learn & Learn.

Reach out to the many resources available & are designed to help small business get up & running.

The internet is rich with information & resources. It can feel uber overwhelming, so in addition to educating yourself & exploring resources, get a business coach and or mentor. Someone who is there to be your challenger & champion. Choose wisely, however. Over the years I have invested in various business programs and supports that have been less that valuable. Be clear on their deliverables, their experience and their own business vision. Ensure there is a good fit for you. And that you clearly see how they have helped others in the past.

There are a long list of things to discover about your self & the technicalities of building a business. From how you feel about selling? What does that have to do with your view of your self worth? (stay tuned for a future post on my learnings about this one!) How to build a website? What about marketing? Social Media? Accounting, taxes etc.

Here are three resources you could start to explore:

Women in Business in Nova Scotia

Great Podcast I find valuable & inspiring

Business Development of Canada’s Page for Women Entrepreneurs

Lesson number five

Be willing to pivot.

One of the enjoyable and equally as challenging points of being your own boss in business is the opportunity to pivot. To stay in the experimenter’s perspective and be willing to call a time of death on a project, program or product when it’s not working. This involves a constant revisiting of your vision, mission & values. It requires reaching out to your customers and deeply listening. In fact, this is one of the most important lessons, I’ve learned so far.

As much as we each have our own vision & dream for our products, services, at the end of the day it is our customers who matter. If there is no one in need of your product or services (or are unaware of their need & unwilling to be educated about it), well, this takes us back up to lesson one through four. 

This has been really the tip of the iceberg of the lessons that have emerged for me today as I’ve reflected on my transition of starting a new business. I hope you’ve found a nugget or two. 

Share what you’re learning below! I’d love to hear and learn from you.

There’s no reason to navigate this transition alone.