Being Your Own Boss: Going Solo Takes a Team

This is the final essay in a four-part series.



The day I published my website was nerve wracking.  I felt vulnerable, yet oddly, that vulnerability was accompanied by a sense of accomplishment. I was setting out on my own.

But not really.

Just as there is no such thing as an overnight success, no one truly sets off entirely on their own in business. There are teams of people in the background, volunteering their time and knowledge, rooting for your success. 

 Assemble Your Business Support Team 

When I first set out, I had a group of 6-8 friends with deep industry knowledge and/or first-hand experience consulting or otherwise working for themselves.  Once a month for the first twelve months, I emailed an update detailing wins and fails.  What business activities I made progress on, areas where I felt challenged, and what was left to accomplish.  I treated going out on my own as a project, complete with a plan, milestones and feedback opportunities.

My obligation to report progress kept me grounded and accountable. 

Because everyone’s business acumen, experience and path are different, a roundtable group such as this serves as an accountability board.  The updates were thorough but not overwhelming.  Allowing them to follow along and determine when it is appropriate to provide feedback.  Maybe there is nothing for four months relating to one person’s area of expertise, but then that month 5 update goes out and they recognize you and your business are now at a stage where their insight will prove valuable.

In the prior three essays, I’ve noted the sheer volume and variety of roles you take on when working for yourself.  Make a list.  Review it with your business support team as early as possible.  They will help identify any blind spots and also assist with prioritizing the ‘must haves’ from the ‘nice-to-haves’.

Decision-makers

Are you creating a low-priced, physical item? Odds are that your supporters will all make a purchase, simply because they believe in you and they control the means of purchase.  They are decision makers of their own funds.  If you are offering business-related services or more expensive products, that pool of decision-makers thins out. 

There are a small number of supporters who know what I do, are clients and have the means to hire me.  Wherever they go, if they see a fit, they reach out.  I am beyond grateful for them because they are incredibly rare.  That trifecta is similar to a rare celestial event that sees a series of planets line up once every ten years. 

The largest set of supporters in my life, and likely yours, are not going to be in positions where they can easily spend their organization’s money. 

Some Words of Caution

Many of your supporters will be your existing friends and family. 

Don’t stop being their friend.  Your relationship existed before you went into business for yourself, ensure it exists afterword.  Your venture may consume your every waking thought, yet your friends may wish to talk about something – anything! – else. Go for a walk.  Play video games.  Hang out with them when you can and be mindful of separating business talk from personal conversations.

No doubt I blurred the lines a little too often at times and am more cognizant of it. 

One day my sister-in-law texted, asking how I was doing and my entire response was a series of positive milestones I’d achieved with clients and publications.  Her follow up, “That’s great. How are YOU?”. 

Do not be frustrated if some of the closest people in your life are unsure how to support you.  Someone who is not active online cannot be expected to like and share every post you make.  They cannot attend every event.  They may have zero relevant feedback to offer you, but what they do offer is far more valuable. 

A friend who sits beside you in silence, to let you know that you are not alone, is a friend to cherish with every breath.

One area where I was very naïve, was not understanding how performative public offers of support could be.  A facilitator whom I’ve met several times, was a very vocal proponent in the early months of my solo adventure.  On social media posts they championed me, encouraging me to contact them if I ever needed advice.  I did contact them.  In fact, I contacted them every time they posted those comments. Not once did they acknowledge or respond. 

There is no way they saw me as a threat.  I feel it is in keeping with their brand - being a helpful person in the community, to be seen as helpful publicly, even if they don’t follow through privately.

Soak It All In

If this is your first time out, some of the advice you receive from your supporters may not be applicable until years down the road.  Either because your business needs to mature through a few fiscal cycles or it undergoes significant changes during that time.

Soak it all in. 

Write it all down. 

Reflect on the advice you’ve received and feel grateful someone cares enough about you to share their thoughts.  When people share their stories, understand they are not giving you a roadmap.  It is more of a signpost.  One day, you’ll encounter that signpost on your journey.  At that moment, your recollection of the story, combined with where you are in your business venture, will let you know how to proceed.  Is it a greenlight? A flashing red hazard? Or a moment to recognize the warning and proceed with caution?

I recall going to lunch with my friend Anna, herself a walking wealth of knowledge.  During our lunch she mentioned another friend of hers who set out on their own.  This person cast a wide net when they first went to work for themselves.  Subsequently, they returned to a fulltime role in the corporate world for a brief time.  It didn’t stick.  Not only did they realize how ill-suited they were to working for someone else, they had a better idea of the niche that did suit them best. The clarity gained made it easier to identify who they were in the marketplace, the service they offered and who their potential clients were. 

Hearing this did not cause me to alter what I was doing or what I had to offer.  I was only 5 months into my first go round.  I never forgot her story though.

I thought of it when I too, accepted a fulltime offer a few years after I launched my business.  I didn’t feel like a failure. 

I thought of it when I realized that working fulltime for someone else just felt wrong.  When I left a position other people thought was akin to winning the lottery, I thought of her story. And I did not feel like a failure.

It is a reminder that success is not a straight line. 

It is a reminder that sometimes we need visceral experiences to guide us when we lose our way.   

It is a reminder that walking away from the one thing that has been a constant in my life since I was a teenager, working for someone else, is not easy.  Remember, I was never the kid with the lemonade stand.  I was the kid who wondered ‘what if?’ and proceeded to act out my next crazy adventure.

At least once a week I second guess my decision. 

It is difficult to let go of things, even things we don’t enjoy, once they’ve become routine. After decades of getting up five days a week to go to the office, sitting in my own office each day, doing the work I want to do can feel … strange. 

Pointless. 

Or overwhelming.

And sometimes, it feels perfect. 


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Glendalynn Dixon

Glendalynn is a writer, speaker & facilitator. She combines humor and reflective storytelling with over two decade’s experience working in technology, education and change management.

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https://www.glendalynndixon.com
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Honesty and Discomfort: Contemplation in Times of Uncertainty

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Being Your Own Boss: The Busywork of Social Media