Lessons Learned As A Solopreneur

Taking the leap to solopreneurship.

I was speaking with someone recently who suggested that they’d like to make the leap one day and leave the corporate world.  They didn’t feel ready yet but suggested that maybe I could share my solopreneur “lessons learned”.  I loved this conversation.  I loved that they wanted to leave their job and make this leap and I loved the idea of sharing lessons learned as I’ve been out on my own now for ten years.  For everyone the experience is going to be different.  What I found with one recent client, that although she wanted to leave her job initially, the issue isn’t just the job, it’s something within you.  There’s more personal growth work that needs to be done otherwise we’ll just encounter the same issues within our new career.

Start your next job while you have a job.

In Michelle Goodman’s book, The Anti 9 to 5 Guide, she talks about the idea of moonlighting while you have your current job.  Some companies have policies against this especially if you are doing the same type of work so you’ll need to check your corporate policies.  However, if you’re a software engineer and an artist, there shouldn’t be any reason why you can’t sell your work.  Whatever it is that is calling you, start doing it while you’re employed.  Take classes, go on retreats, read books, and network with those who are doing what you want to do.  This provides you with a safety net as you venture out into this new world.  I was in such a bubble in my corporate world.  I had no idea there were other people outside our company doing amazing things.

Be on top of your finances. 

When you do make the leap, you most likely won’t make as much money initially.  Be prepared by saving as much as you can and get rid of any debt.  This will make those lean months much more manageable.  I honestly didn’t think this through when I left.  Outside of selling my condo, to alleviate the worry of a mortgage, I just ran out the doors and had to figure this out as I went along.  I had no idea what I was going to do or that I wouldn’t work as a full-time employee again.  I just left and went traveling.

Be willing to work part-time.

When I decided to be a coach, I quit my marketing consulting career to focus 100% on coaching.   I felt this is what I needed to do.  I thought I had to set the intention and let my actions follow so that my energies weren’t scattered.  It didn’t work.  I made very little money, had to use my savings, and ten months went by before I could get a consulting job again.  I still consult part-time today.  I’ve changed my perspective on it though.  Instead of saying, “Ugh, I thought I was done with this type of work”.  I say, “I’m so thankful that I have a part-time project which in essence is paying me to create a coaching practice and write my book”.

Work hard for you. 

Some people are really good at working for themselves.  They don’t need any prodding, they just run around town, build a business and make millions.  I think this is a very small percentage of the population.  For most of us, we’re really good at working for other people.  If someone says, “deliver that to me on Monday,” you are off to the races, writing that proposal.  But if you work for yourself, you are the only one trying to figure out what you need to do and when to deliver it.  There are no deadlines.  There are no meeting presentations to prepare.  This is why I shared in my last post, that you have to ask yourself, each day and each week, “What is going to give me a sense of accomplishment today?”  Additionally, you have to remember that your work day is totally different than when in the corporate world.  I spent all my time in my corporate job going to meetings and writing emails.  That was what productivity looked like for me.  As a solopreneur, productivity isn’t a day at my computer looking at emails.  Productivity is writing for a couple of hours, reading a self-help book, setting up meetings, going to networking events, connecting with new people, and managing my social media posts.  The old way of working is a really hard habit to break too!  I still have days where I’m staring at my various email accounts trying to figure out what to do next.  (The answer is to close my email.)

Connect with others.

When you go out on your own, you often end up spending a lot of time alone.  I actually don’t mind being alone because I find it very contemplative and restorative.  However, if I spend too much time alone, I start talking to myself and my dog way too much.  Isolation isn’t good.  You need to get out and connect with like-minded people.   You need to share your ups and downs with someone other than your significant other and/or dog.  You need to brainstorm with people going through what you’re doing through and see if you can find solutions.  Whether you meet people at networking events, go to meetups or create your own mastermind group, you need others to help fuel you onward.

Be open to a circuitous route.

I like point A to point B.  As creative as I am, I’m also very linear.  I once walked a labyrinth at a retreat and basically ran to the center so I could see what was there and was slightly disappointed when there was just a small rock.  I realized at that moment that I was supposed to be enjoying the journey.  I’ve lightened up over the years and no longer feel the need to know what’s going to happen.  I like the journey now and I like surprises and changes.  Maybe it’s because being a solopreneur isn’t linear.  The path I’ve been on since I left my corporate career has been a winding road.  It is going places that I wouldn’t have imagined when I left in 2006.  I love where it’s going and I can’t wait to see where it takes me next.


For me, I’d say that overall being out on my own has 100% been the right choice for me.  It hasn’t been easy.  It has been a roller coaster.  I didn’t know what I was doing when I made the leap, I just knew the status quo wasn’t working anymore.  The quote from Anais Nin perfectly describes it: “And the day came when the risk to remain tight in a bud was more painful than the risk it took to blossom”.  So, go blossom, again and again, because this one leap won’t be the last.

Anais Nin






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