29 Comments

There is some absolute GOLD in this article, my favourite part was your overview about what's actually important:

- Solving a valuable problem for an engaged audience

- Cashflow

- Momentum

Couldn't agree more.

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This echoes a very true sentiment. At the end of the day you are there for you because whilst those around may support they will never truly understand everything that went into a decision or milestone. And vice versa too!

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This resonates well with me as I quit my job last year to take a sabbatical. Now, I'm doing my best to be independent and build my business as a solopreneur.

The process is so damn hard. I thought I would give up multiple times, but glad I keep pushing myself.

Swimming upstream is also tough. But I realized this is the process I have to follow.

If I had turned back time, I would have taken myself less seriously and extended my time horizon to succeed in the new pursuit, so there would have been less pressure for me.

But, overall, I know it was a right choice to begin with.

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Thanks for sharing, Wyndo, and being open and vulnerable about how tough the process can be. The instinct you have about this being the right path should be enough - keep it up and the success will come.

The balance between throwing yourself into hard work and giving yourself grace is tough. I comfort myself with the belief that the results will come slower at first...then faster than you can imagine.

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This was so comforting to read as someone who just lost her job and decided to finally give working for myself a shot!

There is a lot of advice around building up your business next to your day job on Substack which has been making me doubt my decision. I tried doing that for the past 3 years but it was really hard and I was bound by so many restrictions and policies. Like you, I was always afraid that I would never go for it. So now that I am, I feel quite relieved.

It doesn’t help that like 50% of people I share my plan with ask me if I have considered <insert amazing corporate job opportunity> instead. So it helps to know that I’m not alone in getting mixed messages and needing to mainly be my own cheerleader (although my partner and family are really supportive)

In other words, I do give a sh*t about your career transition 😉 in fact, I feel inspired and excited for you!

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Congratulations on your decision, Anna. The clarity you'll get some taking firm action and moving will be worth it, however the road winds.

I count myself lucky to have great support from my partner and my family, and now you from you as well. I'm looking forward to staying in touch and swapping tips along the way!

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Thank you Graeme, that sounds lovely! Let's definitely stay in touch and exchange tips! (side note: I can't wait to get to a point where I actuallty have any tips to share on this haha)

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This is too true and while it’s been hard to hear, I’m so relieved I’m not still living in ignorance about it because it always justified staying:

They didn’t give a crap about what my title used to be, the size of my former team, or any of the other things that are so prized within the corporate matrix. Your money is no good here, Sir.”

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Within the corporate matrix, job titles differ so much that it doesn't really count for much even IN the ecosystem, never mind outside it. Experience and results (and ability to make your new leaders look good) are far more important.

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I feel you and I hear you! Every time you ask yourself: ‘What if it doesn’t work out?’— rethink. What if it does? That’s why you do it. That what you follow. Keep going!

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Even in the hard times, you can ask "how could I make this situation as great as possible?". Got to keep fixing forward. That's what separates success from the many who give up.

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I just left a 7 year corporate job at a big company and it's been a thrilling and terrifying transition. It's only been a month since my last day. One area where my experience is different, I find a lot of people care. Maybe it's because I do a lot of volunteer work with a cause that isn't career minded, and I am an active church member, but I've had a bunch of friends check in on me constantly.

They ask how it's going, they want me to succeed, and they seem to want the best for me. Maybe it's that people in corporate America don't care once you drop out. But there's an entire world of people who are not on the grind and they care a lot about people who are taking risks to be themselves.

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I'm happy for your difference in experience, Sean. I think the blame for mine lies at my own door, where I over-invested my time and emotion for too many years in the people of corporate America.

I hope to continue to build friendships and community like the ones you have along the way!

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I’ll be your friend. You seem like a great guy.

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Extremely refreshing article and very well put. As someone that's just left their "dream" corporate job in favour of taking a risk with entrepreneurship, this has helped ease some anxieties I have been facing. The one thing that always keeps me going is that each morning I wake up with no cognitive dissonance about where I am in life. Sure, I feel anxious about the future, but I am always flooded with a sense of "this is exactly where I need to be". I never felt that way in the corporate world, and if I did, it was often an illusion! Good luck with your next steps, excited for you!

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Thanks, Kavi. I am writing about something more related to this now - that true authenticity is when your thoughts, intentions and actions are fully lined-up. Often we think that's the case but if we stop and examine closely enough it is not always true.

It's great that you're already feeling a difference. I wish the the very best for your onward journey. It sounds like it has already been a success!

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Nobody caring is so true. This paralyzed me for years, but people have so much going on in their own lives that really, nobody thinks about you except for very immediate friends and family. It’s very freeing once you realize that.

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Tremendously so! What are you doing with your new-found freedom, Robbe?

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Oh, well I quit my cubicle life as a government contractor and went all-in on running, over the past five years have built it up to where we're now the world's number one site for running shoes and gear reviews, 100k subs on YouTube, top running podcast in the U.S. and have traveled the world over, making more than I ever did at govt. I'll never forget the day my contractor lead tried to convince me it was a bad idea and too risky (like your warm lead). Cut the rope and never looked back.

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Amazing, what an inspirational story. Thanks so much for sharing, hoping to follow in your footsteps. Pun intended.

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Awesome Graeme, such a great decision you made, I can only respect it.

I am battling with this myself now...

Keep us updated on your journey, look forward to seeing what you accomplish!

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Thanks, Stefano! Good luck for your own journey, too. Happy to chat whenever (with no punching) 🫣

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Very few people will applaud your decision. But, it's your life!

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That's been one of my biggest pieces of progress. Not needing other people to applaud my decision to feel sure that it's a good one.

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I care x

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Love this. Also love the realisation that nobody cares what job title you used to have, they want to know what you are doing now.

I've been grappling with a career change for a while, fretting over job title and my 'career identity' was what held me back for a while... none of it matters!

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My experience and feelings mirror what you describe. What felt liberating to me about people not caring what I do: most people didn’t bat an eye when I said i was working for my own company. I read this to mean they thought of me as far more open and capable than I thought of myself.

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Nobody is ever paying as much attention to us as we believe they are. This gives us permission to live life exactly as we like. Any fear of judgment stems from a made up story in our heads, and is therefore irrelevant. We get one go at this, let’s make it count.

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That Dan Koe quote was one of my big motivators to make a change too!

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