Maggie Lynn Olson Coaching

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Is Entrepreneurship Lonely?

In December of 2013 I turned in my 2 weeks notice at my corporate job where I’d spent 8 years working. I enjoyed the job and got to do a lot of fun things - photography and videography, documentation creation (this was actually a lot more fun than it sounds 🤣), training customers and helping a lot of high level sales reps and executives at the company. I enjoyed most of the people I worked with…except for my boss. 

I didn’t quit my job, I quit my boss. 👀

When I called the meeting with my boss, the engineering manager and the HR manager I was SHAKING with fear (and, if I’m being honest, excitement). This was totally not like me to just - quit. 

I wasn’t this bold. 

I certainly was never this rash. 

I had NO CLUE I was waking up that morning to quit my job. 

And I was afraid of what people would say but I’d had enough. It was literally like at the peak of a movie where the heroine finally takes a stand and says, “no.” and finally takes a stand for herself.

I had been told a few days before that I needed to work more hours (overtime) because my cohorts were working overtime. So to make things “fair” I needed to work more as well. When I said, “but I don’t have enough work to keep me busy” I was told to “find work to do”. Which I had gotten in “trouble” for a few months before for doing because I wasn’t “doing enough” in our group and was spending too much time doing pet projects for the higher ups - even though I was ahead on my projects and was waiting for others in the group to finish their projects so that I could put the final touches on things. 

Talk about a mind game.

I was at my wits end and I knew that my photography business was busy enough for me to let go of the security of a corporate job. Sunday Scaries usually started on Saturday evening and sometimes on Friday at 3pm as I was leaving, I was already dreading coming back on Monday. I would get all worked up about all the things that I didn’t want to be doing all week long at work. I walked in at exactly 630am and out at 3pm because I didn’t want to be there a minute longer than I had to. And really, I was busy enough outside of work with photography and teaching yoga that I had to be on the dot in order to fit everything in each day. 

After being told I needed to “do more” I called that meeting. And as those three filtered into the room I stood up, took a big deep breath and said, “I’m done. I quit. I can’t do this anymore. I don’t have enough to do and apparently me finding things to do are the wrong things to be doing. My photography business has gotten to the point where it’s a full time job. What are my next steps for quitting?”

The engineering manager clapped and congratulated me with a, “WOW!!! I’m SO PROUD of you for growing your photo business to the point of full time!! Be proud of yourself!”, my boss’ jaw hit the floor and the HR manager just scowled at me. It was December 13, 2013 and I knew my boss (and probably the HR manager) was scheduled to take most of the next couple of weeks off. I had just created a mountain of paperwork and hustling for them. Was it a dick move, yea maybe. But I had been put in a corner for far too long and I knew I was meant for more. I was done being walked all over.

I walked out of that room feeling so LIGHT and FREE. Like a literal new person. I had shed a layer of myself that I held onto for far too long just because I wanted to “fit in” and “have stability”. Over the next two weeks as I wrapped things up I knew they were in for a big surprise when they realized how much I actually packed into the 40 hours that I was in the office each week. 

I was also in for a big surprise once I left the office. 

Yes, I was getting the freedom I desperately craved. The ability to create my own schedule, work when I wanted and make as much money as I wanted. But I would also soon find out how lonely (and HARD!) working for yourself can be. Over the next few months after I left I realized that things were kind of like the movie Ground Hog Day at my house. Everyday felt the same and while it was amazing - it was also really freakin’ lonely. 

In an instant almost all of my friends were no longer just a walk down the hall. Suddenly there was a barrier I was no longer on the inside of. And there wasn’t much that we had in common any more. We couldn’t joke about work because I wasn’t part of that. They didn’t understand the demands of being an entrepreneur and I didn’t know what was going on at “work”. 

What did I do? 

Over the next few years I started learning more about the art of networking and how important it can be for a business owner. And important in more than just being able to pass leads/referrals. Important in the way that you can be around people who are in the same boat as you. And essentially the “water cooler” or “coffee pot” conversations that happened at work now happened at networking meetings and galas and events. Being able to connect with others to say, “I’m having these issues.” and hear, “oh, me too! I thought I was the only one!” was a relief. Having someone to talk to about business is so good for any entrepreneur. 

It took me a long time to “find my people” as far as networking goes. I tried the full gamut of things - but never quite feeling like I was “enough”. Finally I told myself to give it up for a while. Then in early 2021 after closing down my yoga studio and switching gears to coaching (and feeling really really lonely and isolated in my business), my coach invited me to an online networking group. And for the first time in a long time I felt seen in a way that I had been searching for for so long. I was able to be myself and not fit into some sort of mold. 

It’s taken me a while to find the evolving voice that I have now - and I think one of the best things is that I’ve been able to understand myself in a way that I can “fit” into any group and feel welcomed there. I’ve done the inner mindset work with myself so that I know my importance in any situation. That I can be myself in an unapologetic way and that I’m not afraid of what others think. The best part is knowing I have a community of other entrepreneurs that I’ve met over the years that understand the ups and downs of being an entrepreneur. And don’t get me wrong, I have amazing friends and family outside of the entrepreneur space - but just like in a corporate job, when you have people in your corner it feels so much easier to get through some of the mundane aspects of job/business. 

What does all of this have to do with coaching?!

This topic is something that comes up A LOT during coaching calls. SO MANY PEOPLE FEEL LONELY IN BUSINESS. Many times it’s the thing that seals the deal to closing a business - “no one understands what I’m going through or how to help me.” Being lonely in business is also something that keeps people from going into business. I can’t tell you how often this topic comes up but I’m also so glad that my clients feel safe to be able to tell me these things! 

How can coaching help?

Coaching gives the space to speak about these feelings and to explore them. And yes that sounds real voo-doo woo-y but knowing you have someone that is on your side and in your court can be so helpful when you’re working through some of these feelings and thoughts. A coach will help you navigate those thoughts and do some of that inner work with you to help you understand what to do when those thoughts come up again. 

If you’re thinking, “how in TF will that help me?!” I would ask you, “what if it DID help you to shift your thoughts?” What if shifting your thoughts could expand a piece of you to grow more? What if expanding your thoughts and shifting your thinking could unlock more in your business - more sales, more money, more time, more! 

When you start to work on your inner thoughts and understand what makes you tick you wind up opening up a whole new level of opportunity in your business and usually that is the trigger to leveling up your income. 

And if that’s you, girl, I feel you. And I invite you to come sit at my table with me. Grab yourself a spot on my calendar and let's talk! I want to hear all about where you are at, what’s holding you back and where you want to be! 

If you’re interested in booking a free 1:1 discovery call - do that here:

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