If I had it all to do over…

If I had it all to do over...

I’m in the process of closing my business… and it feels like ripping the sharp shards of a shattered heart out of my chest.  I knew it would end eventually, but I didn’t see all the grief it would bring with it.  I’m left hurting, and questioning,  “If I had it all to do over again, what would I do differently?”

I accepted that the business would have a not-too-distant end.  I’d had to accept that, after years of fighting with myself. I just didn’t want to give it any more of my energy.  I wasn’t the right person to build the remaining systems that it would need to truly be sustainable over time.  But if I had it to do over, would I rather have just grinded on to the bigger goal?

Would I keep working on it longer?

I’ve debated whether choosing to stop developing the company, where I did, made me a quitter… Is just pushing through to some more lasting “end” what I’d do differently? No. I couldn’t do it.  I’d been at this company for 8 years.  8 years is a really long time to stuff down a bleating heart that longs to do something else.  I already silenced my feelings with food and obsession over short-term goals.  I spent years forcing myself to do work I didn’t have passion for, as a vehicle for geographic freedom.  I think I made a solid choice by seizing that freedom while I could.

Would I stop working on it sooner?

Once I realized that I didn’t really love running this company,  should I have turned in search of a greater passion to fuel the journey?

It’s true that I’m a huge fan of  jumping from thing to thing.  However, I want something that feels (to me) like a stable foundation to jump from thing to thing, upon.

There’s a huge ” motivational culture” around the  web these days to “quit your job and live free!”  But I was $40k in debt when I started this business… that’s not living free.   I started actively inquiring about what I might want to be doing instead, in 2012.  It’s 2017, and I’m still at it.  5 years on that quest, and  I still don’t know what the hell kind of vocation I’d find any lasting happiness in.   But I also don’t have any more credit card, auto loan, or graduate school debt.  I’m really glad I didn’t give up having an income over that period.

I would delegate more, sooner.

I knew from the first year of this business, that my dream was to have it function without me, while I explored elsewhere.  I was afraid to step out, though.  I thought I needed more income first, before I could afford to offload the work that kept me tied to Los Angeles.  The more I wanted to get away, the harder I thought I had to dig in and work to build that freedom.  It wasn’t until circumstances arose that took a gash out of my income that  I realized I could drastically cut my living expenses by getting out of LA as soon as possible.  If  I had it to do over again, I’d question my assumptions about how much cash flow I actually needed, and channel more cash into my geographic freedom goal.

I would be more myself.

I knew I wanted to turn this business into a passive income generator for me… but I sort of kept that a secret.   I thought in order to sell, to train, to lead, I needed to have a big lofty vision, and enthusiasm to enroll others in that vision.  I thought in order to build relationships, people needed to have a sense that they were “for life”.    I thought I needed to be someone else, in order to be a successful business person.

Sure, I have elements of the clever strategist, the outgoing organizer, the ambitious visionary, the obsessed number cruncher, and the devoted caregiver.  But those aren’t all I am.  Looking back, I realize I worked hard to hide the wandering, introverted, contemplative, quickly changing creature I also am.  It’s exhausting to hide parts of yourself, and it leaves you burned out and tied up in nots.  If I had it to do over again, I’d try to trust that *all of me* is okay and allowed to come to the table.

I would risk not knowing.

By burying parts of myself, I spent a decade learning how someone I was *trying to be* does business.  I don’t actually know what *I* can do in a vocation, or what I want from it.  I don’t know what I’ll find next… maybe a new business, maybe simple work that can sustain my continued travels, or maybe even a life that looks more “normal” for a while… But I don’t know, and that’s AWESOME.  Not knowing means I don’t have to force anything to happen.

In this business,  I spent a lot of time figuring out how to force things to happen.  I held myself responsible for a lot of outcomes… basically all the outcomes.  I put so much pressure on myself to know everything, and wrapped myself up in an illusion that I had much more control over the world than I actually do.  It’s taken a lot of work to make friends with not-knowing.

I would be crystal clear with what I do know.
  • That the people who worked for me mattered, deeply.  I wanted them to feel valued and trusted.
  • That we provided a great service, and saw huge changes in the lives of our clients.
  • That business was a really good place for us to all practice the “tough stuff” of boundaries and agreements, and general adult-ing.
  • That the wellbeing of the humans involved was more important to me than money.
  • That  I wanted an unconventional life, and my personal engagement in all this might not look the same over time.
  • That there’s a lot of things I’m not great at, and I’d love help with.
  • That human-ing is hard, a lot of the time.  So let’s be really gentle and playful with each other, while we do it.
I would focus on discovering how be gentle with myself, while I learned.

If I had it to do over again , even when a sense of scarcity and fear made me feel like I couldn’t possibly rest until I had it “all figured out”, I’d find a way to seek out beauty and joy, each day.

If I had it to do over again, I’d go in with the assumption:

“I’m enough, just as I am.”

Yes, if I had it to do over again, I’d definitely be more of my unknowing, playful self.


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1 thought on “If I had it all to do over…”

  1. I love you “Lady Octopus.” How that lesson (what was it 7, 8 years ago) has really showed up as a recurring theme. However, your teacher may have been right and wrong- while you can’t put out 8 fires at once, you can be a whole being that’s multifaceted. Keep digging into that idea that play makes life gentler- perhaps that will be the center of your next big thing. ❤️❤️❤️💃🐙

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