What is the most unexpected challenge you’ve faced as a founder?
Morgane Granier
26 replies
Being a founder comes with countless challenges, but some of the toughest ones are often the least expected.
Let’s share stories about those surprising obstacles that caught us off guard—whether it’s a team issue, market change, or something totally unexpected.
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Morgane Granier@morgane_glt
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One of the most unexpected challenges I faced as a founder was managing my own energy and mental resilience. Balancing the constant ups and downs, staying motivated, and avoiding burnout proved to be just as critical—and difficult—as tackling any business problem 🥵
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Sparky
For a bootstrap founder, a limited marketing budget can indeed be a big challenge.
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@liu_kexin Bootstrapping on a shoestring budget is no joke. Finding creative ways to stretch every dollar can be exhausting but also super rewarding when it pays off!
Elon Jump
That you have to actually talk to your customers 😭
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@ag94 hahahaha YES! Saas founders usually think they won't have to 'cause they want it to be selfserve services, but spoiler alert... we have to! 😂 Been there too but I'm actually starting to like talking to my users
(Love your comments btw. Second punchline you're throwing under one of my discussions)
Self Doubt. As a first time founder
I struggled with realizing my value at first.
Learning so many new things and wearing different hats can be exhausting.
I fail every single day in one way or another.
Now, instead of feeling like an imposter I remind myself that I’m human.
There’s things I don’t know how to do, things I don’t like to do, and things I will never be the best at.
That’s okay.
My best quality is being aware of what I’m capable of and if I can’t get it done I’ll find my clients someone who will .
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@ashley_bergeron So relatable! Imposter syndrome can sneak up on you, but your self-awareness is such a superpower. Keep reminding yourself that progress over perfection is what really counts!
For me, the most unexpected challenge was learning how to effectively delegate and let go of control. As a founder, it's tempting to want to be involved in every decision and handle everything yourself. But I quickly learned that's not sustainable and can actually hold your company back from growth. Building a strong team you can trust and empowering them to take ownership was a big mindset shift, but so critical for scaling the business and maintaining my own sanity! 🧘♂
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@noahchristopherbennett Letting go of control is such a big shift, but you nailed it—trusting your team and letting them take ownership is a game-changer for scaling and keeping your sanity intact!
Totally feel you on that. For me, the constant roller coaster of emotions and self-doubt has been the toughest part of the founder journey by far. It's a daily battle to stay positive, believe in yourself and what you're building, and not let the lows destroy your motivation and energy. Learning to embrace the chaos, take care of yourself, and keep putting one foot in front of the other is a skill that I don't think gets talked about enough. Stay strong! 💪
Balancing work and life was tougher than I imagined. It took more effort to manage than I expected.
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@noora_mccluskey I feel you on the work-life balance struggle! It’s easy to let things blend when you’re passionate, but finding that line takes serious effort. Glad you’re tackling it!
Definitely managing your own mindset and motivation. Especially in the early days when it's a rollercoaster, you have to be your own biggest cheerleader. Finding little wins to celebrate and ways to recharge is key to avoiding burnout. Staying optimistic through the lows is a real skill!
One of my biggest surprises was realizing how challenging it can be to manage unexpected team dynamics. It’s one thing to plan for market changes, but people issues can really throw you off!
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@elido_dial People challenges are always the sneaky ones that catch you off guard! It’s a whole different beast compared to market shifts. You’ve got this!
I was caught off guard by how much time and effort goes into maintaining a positive company culture. It’s easy to focus on the product, but keeping the team motivated is a whole different challenge.
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@rose_linda Keeping the team motivated is a whole job in itself! It’s so easy to get lost in product goals, but without a strong team vibe, things can quickly go south.
I was surprised by how difficult it may be to stay motivated during terrible times.
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@nathaniel_cross It’s so true, staying motivated when things aren’t going well is one of the hardest parts. But those tough times really do build resilience!
I didn't anticipate dealing with unanticipated regulatory difficulties. It was a serious setback.
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@amelia__waters Regulatory hiccups can feel like a sucker punch—totally get it. They’re such a wild card, but getting through them just makes you a stronger founder!
Probably managing yourself, especially in the early days where it is just you (+ co-founder(s)). Sometimes it's difficult to get going and get in the flow of getting things done. I think there is a lot of focus on how to manage teams, how to raise, growth hacking, ... while not too much on managing yourself. It's a learning curve for sure.
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@robin_poelmans Completely agree. There's a lot to think about and manage at the same time. Keep your vision alive, nurturing your relationship with your co-founder and ensure you're on the same page, but also get shit done product, marketing and growth-wise.
So challenging but so exciting!