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  • Jenny

Day 40 of Self Employment: From Corporate to Cocktails (and Content Creation)

Updated: Dec 12, 2023

Going from working almost a decade in a corporate environment to suddenly being self-employed (even if at will) has been the biggest life change I’ve experienced to date. It feels much more dramatic than going from college to starting a full-time. I think it’s all related to social norms.


It’s the norm to graduate from college, work a job at a stable company, turn that job into a career, and continue to be employed to earn a steady income - whether it’s by the same company throughout the years, or switching to a similar one in the industry. It’s the norm to climb the corporate ladder and gain more responsibilities and earn more income. I was on that track. And I ended it abruptly.


I was a senior manager in a corporate headquarters environment, on track to become a director in my next role. I was doing everything I could to gain more responsibilities, get more exposure, and take on projects and experiences that would set me up for success as a director. I was going through all of the motions, yet… I wasn’t all that excited. I wasn’t feeling fulfilled by the accomplishments, and I couldn’t get myself to truly care.


At the same time, I was managing my Instagram food blog for the past 2 years and learning every day. I was creating on it daily and through it, had formed relationships, learned social media marketing, and started receiving interest from local and national brands to partner. After reaching 20,000 followers in May 2023, more opportunities came my way. The more opportunities landing in my inbox, the more I wanted to test and learn concepts, the more content I put out, and the more momentum I had with follower engagement and growth.


I’d hit a point in September 2023 where I couldn’t easily manage both my day job and the content creator opportunities without sacrificing quality on one of them. This was around the same time I realized my passions were with creating — yes on the food blog I started, but I also realized I had suppressed my dreams of starting and creating my own business. On Labor Day Monday (September 4, 2023) I’d decided I wanted to open my Italy-inspired cocktail bar, and 48 hours later on September 6th I would put in my notice. September 20th would be the last day in my corporate career.


To say I left and “never looked back” would be a total lie. I look back all the time. I think about how I felt working a job where I wasn’t always challenged, yet I always got a paycheck. It was kinda nice. I think about how I now feel challenged every day trying to learn how to start a business, gain better content creator skills, and build structure and new routines with self-employment, yet… don’t always get a paycheck and now have variable income. I know it’s worth it for me, but it doesn’t always feel good.


I juggle the rational part of my brain which still fully recognizes that corporate work is stable and relatively high income, with the creative and riskier part of my brain that I had inevitably suppressed. The great thing is that I no longer have to suppress the creative side. Instead I’m learning to find rigidity and routine in this completely different life. And within all of that, I feel much more fulfilled as a whole.


Finding routine, building new habits, and adjusting my mentality hasn’t been easy. But these are the 3 things that have kept me going over the last 40 days. They help ground me when my mind wanders to unhealthy places, when I have feelings of doubt or regret, or when I feel less valued with the decision to be self-employed.


Finding Routine

The routine previously was the Monday through Friday, 8 to 6. It was that in those hours you’d dedicate your mind to doing whatever corporate asked of you - but you knew you could mentally sign off in the evenings and on weekends. While it wasn’t always ideal for me, the structure was oddly comforting, mostly because it was predictable. Now that I don’t have any pre-set structure in the day, I need to create my own. A schedule that includes time I dedicate to running and working out (this hasn’t changed vs. when I worked in corporate, but is changing with the season and later sunrises), to content creation, to uploading, to writing, to doing emails (this never changes), to learning how to run a single-member LLC. I can’t say I have fully figured out the routine yet and every day does look different, but I’m trying to embrace that going off schedule is a beautiful privilege, and learning to be adaptable is a skill I’ll carry for the rest of my life. Today I really wanted to start my day with a run. But it’s cold and raining, and the afternoon looks clear. So instead, I started my day with short form uploads (Instagram and TikTok, and this week I’m committing to uploading all TikToks to YouTube Shorts as well), responding to emails, reviewing some legal documents related to my LLC, and writing this blog. I’m planning to go for an early afternoon run.


Building New Habits

Instagram and social media can be as easily harmful as it is helpful. The IG and TikTok spirals I’ve been on are countless. You get sucked in and can barely pull yourself out. You’re consuming without any intention and you’ve lost sight of the day, what you wanted to accomplish next, and what goals you’re working toward. It’s a scary place to be. I could easily be on social media more than I was previously when I was still working my day job. I have more content I’m working on and more content to upload. But I have the goal to be on it much less than before. I want to fill my day with intention. There are 10 things I could work on at any given moment that get me closer to my goals. Getting sucked into the platforms is the last thing to get me there. I’d used to upload a post and re-watch or refresh it for the first 10 minutes it was live. It really did nothing except make me sad if a post didn’t get good engagement right off the bat. Now I try to “set it and forget it.” Let it go live and run its course without checking it too much. This doesn’t always work of course; I need to constantly remind myself of what I’m working toward and what will get me there.


Adjusting My Mentality

The pervasive thoughts here regard my worth and value. For whatever reason, I felt my worth was tied to my job and income, and potential for a better job and more income. I really wrestle with what my worth and value are now that I’m self-employed. Over the last 40 days I’ve gotten in a much better headspace about this, with the help of great friends and also my followers. I had a bad mental health week a couple weeks ago and was open about it on Instagram stories. I had several people respond over DMs to remind me that I do add value: that I had helped them find footing in a new city, that they had taken my recommendations for big days and big celebrations, and that they enjoy following all the spots I check out and look forward to all my posts. The value looks completely different from before (and before, the value was mostly added to me actually, in the form of a paycheck) and now I’m actually adding more value to followers of my content. I’ve put my time and energy into creating content and higher quality output, and this directly benefits the people who consume it. I’ve learned to disassociate income with success, and I think we all can agree that money does not equal happiness.



Thank you for reading and following along my journey. I am grateful and have learned so much from the people who engage with my content. Engagement is not one-way — it’s a two way street that communicates and grows and evolves. If you ever have thoughts or feedback, please do not hesitate to reach out. I value human connection and finding mutual understanding the most.


Cheers to more content, figuring out how in the world to start a cocktail bar, and continual growth. During good days and bad days.


Recording a frame on Wednesday 10/25 for my most recent YouTube video. This one didn't make the cut haha:


1 Σχόλιο


Jennifer Egan
Jennifer Egan
30 Οκτ 2023

Loved reading this 🫶🏼 so relatable, even to those who aren’t self employed

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