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3 *Big* Mistakes From A First-Time Entrepreneur

1 year into quitting my job as an innovation lab product manager to become an entrepreneur, I reflected on 3 big mistakes I made on my early journey:

1. I quit my job with the goal of starting my own company.

I naively set aside a year to build my own company. It set me up for failure in my own eyes. Building a business really is hard and you can't put a timer on it.

In hindsight, I actually quit my job to learn new skills, test some of my own ideas out and figure out my next step—maybe that's a company, maybe it's consulting or maybe it's a career switch.

I'm still struggling to forgive myself for not meeting my original ridiculous goal.

2. I spend the first 6 months building my projects in the dark.

I built my first few projects in the dark, too afraid to share my progress (and failure) in public. I didn't think anyone would be interested anyway because I hadn't "made it" yet.

I finally gained some courage 6 months in and started building in public and sharing my learnings openly. What happened next was shocking—not only were people interested in what I was doing and what I had to say, but they started asking for my advice!

Turns out, people are interested in how someone has taken their first few steps. And it gives you credibility to advise on a topic much quicker than you'd think.

3. I fell victim to shiny object syndrome and didn't specialize.

The product ideas I've worked on so far span remote work, productivity, product management, e-commerce and idea validation. I've also learned a fair amount about landing pages, cold outreach, lead generation, social media marketing and copywriting.

What I should have done was either pick a problem space and stick to it for 6+ months or pick a specific skill and master it. I would have had a higher chance of building a successful product or starting a service business on the side.

However, this is the mistake I regret the least because I got to experiment a tonne and learn a bunch of different skills. But going forward, I need to focus more.

A lot of these reflections came out of writing the first article of a multi-part series on my entrepreneurial journey: Bye-bye Corporate World, Hello Entrepreneurial Rollercoaster

Give it a clap on Medium if you enjoyed it.

  1. 3

    Well done thanks for sharing.

    The one thing I think that is underestimated in quitting you job is that it does give you time to reflect and figure out your next steps and find your shortcomings. I think this is important and most people never get to experience.

    1. 1

      100% agree. I quit on purpose without a plan because I needed time and energy to figure out what it is that I want to do (and to learn how to test ideas.) I was extremely lucky in that I had a runway so I could quit on a whim, but I do think it's worth it for a lot of other people to save up money so they can quit and get this headspace.

  2. 2

    Thanks for sharing!!

    1. 1

      Anytime! Thanks so much for reading and commenting, I appreciate it.

  3. 2

    Great read Lena. I quit my job two years ago and it took me 18 months to make my first dollar online.

    I truly believe that the only way you can learn from these initial mistakes is by experiencing them first-hand.

    Failure is an asset that compounds over time. With every failure, you'll collect a wealth of insights about works and what doesn't;t.

    If you combine this knowledge with the ability to consistently keep trying, you're almost certain to find traction at some point.

    1. 1

      Thanks for your thoughts, I love how you put "failure is an asset that compounds over time." That's pretty profound.

      I've been thinking a lot about failure and advice. And my conclusion is people seek advice to try and avoid failure but honestly, it doesn't work. Precisely because you have to live through it yourself. So many things I did my mentors told me "don't do it like that" but I just had to try it myself. And fail. Only then did the lesson stick.

      Advice is great and I still seek it on a regular basis but am becoming cognizant of the fact that it's a safety net. Sometimes a false one at that. Much quicker to just go in and try something yourself.

  4. 2

    Interesting read..

  5. 2

    Thank you for sharing. It takes courage to quit your job. Definitely being a founder is a lot harder once you get your feet wet. The pain level is up there and so is the reward. It's a perspective that is hard to grasp when you work for someone else.

    1. 1

      Nothing prepares you for the entrepreneurial journey. It's the biggest rollercoaster I've ever been on but the most rewarding experience of my life.

  6. 2

    Thanks for sharing! This resonates with me. I just recently quit my job as a software consultant in order to pursue building a company, so you can imagine that feeling of finally being liberated after years of hard work for others.

    It sounds like you've learned so much in the course of a year and you consider that a win! Things get much easier once you get experience and the necessary skills to deliver a product. I've done that for other projects so I told myself, "I should be able to do that for myself" so here I am starting my journey.

    Good luck to you @fadedred!

    1. 1

      I felt really liberated and positive and free for the first few weeks after quitting. Then at the 3-4 week point, it suddenly dawned on me that I had no idea what I was doing. My first product idea failed miserably (or I failed and didn't know how to move forward after getting initial feedback.)

      Doing projects in corporate vs. on your own is quite different in my experience. But the corporate experience definitely helped a lot. Wishing you the best of luck on your journey and reach out on twitter to @LenaSesardic anytime! :)

      1. 2

        Thanks for your honest reply.

        Definitely will connect on twitter!

  7. 2

    Great insight. Building in the dark... Thats me currently always feeling people will think i'm some loon for thinking I can create something. Maybe they will, but I'm going to start sharing my progress more. THANKS

    1. 1

      Do it!! It honestly makes everything so much better. It made me feel less like a nobody (not that you're a nobody but it's how I felt)! Good luck!

  8. 2

    Thanks for sharing! It's always super helpful to have feedback regarding where we should focus our attention on. I think the biggest challenge is to put yourself and your project out there even if you know there is a lot of room for improvements. Good luck with your journey!

    1. 1

      That's definitely the hardest battle. And I have my first ever mentor to thank for that. He really pushed for me to build in public on Twitter and just throw a first bad version out of a product. Really saved me that guy and I started off stronger than I would've on my entrepreneurial journey!

  9. 2

    Thanks for sharing Lena, very good reflections. I think that error #3 is the most difficult to recognize and avoid.

    1. 2

      I literally still fall prey to it... but I have more clarity on what I want to do right now so all the shiny objects are at least somewhat related haha. Need to continue working on my focus though.

  10. 2

    Really insightful advice. Especially to share our process with like-minded people like us!

    1. 1

      Super happy to hear it. Thank you for reading.

      1. 2

        Is there a book or person who most influenced your way of thinking about entreprenruship?

        1. 1

          There's a tonne for sure. Alex West (alexwest.co) was a big influence just because he's been so transparent about how long it took him to make money from his projects.

          Also a big fan of Rand Fishkin and his book Lost and Founder - again, super honest, great values and paints a more accurate image of venture capital.

          I recently read Founder's Mentality and it really resonated. Highly recommend that book.

          1. 2

            Great book for sure. Especially the part about the three predictable crises of growth. Also in the last part of the book they presented ways to avoid the crises

            1. 1

              Oh you've read it nice! Yes great book. I particularly liked how it talks about companies that fail during a crisis and how they were struggling before that and the crisis just exasperated their situation.

              1. 2

                Yeah the examples of the comapnies were very helpful for sure

  11. 2

    One of the "drawbacks" of starting down this road is that you have to become a real generalist and once you do you really only need to be about 70-80% good at each thing if the product is good enough. Later you can bring in people for that last 20-30%. If you ever go to get a job after years of this everyone wants a specialist who is 100% good at one thing. Companies don't value generalists so maintaining a current specialty is important if you decide to go back to the corporate grind.

    1. 2

      I agree with what you said about becoming a generalist to go down this road and then having to be decently good at many aspects (design, sales, marketing, writing etc.) But in my experience, some companies do look for generalists. I was a product manager for 4 years and was always a generalist. I specifically worked at startups though where the same mentality as the one you mentioned is needed - need to be able to do a bunch of things quite well. But some companies for sure don't appreciate that kind of general experience.

      Good thing I likely will never return to corporate lol.

  12. 2

    It takes some people years to learn these and they still don't course correct. Well done!

    1. 1

      Thank you for the kind words, means a lot.

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