3 Ways To Overcome Entrepreneur Challenges

Advice from founders and entrepreneurs answering the question “should I quit my respectable job to do something I’m truly passionate about?”

3 Ways To Overcome Entrepreneur Challenges

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One of the most common dilemmas we come across on a day to day basis is:

“Should I quit my comfortable, respectable job to do something that I’m truly passionate about?”

Sounds familiar, right?

Over the last 10 years, Entrepreneurial careers, Founding Startups, and Thought Leaders have become increasingly aspirational. Everyone wants to be the next Elon Musk, Reddit, or Casey Neistat. Everyone wants to solve a problem, do work they find meaningful, and have an impact.

We think this is pretty amazing. The more people there are that quit their job in finance to start a social entrepreneurship, or a sustainable company, or try to solve global poverty, the better.

That doesn’t mean that it’s easy to make the transition though. Ultimately, entrepreneurship is often misunderstood, risky, even expensive if done the wrong way. So It’s natural that people would be wary of leaving their jobs behind to pursue something with few guarantees.

That makes sense.

But… we feel it’s our job to demystify some of the major hurdles that prevent some of the brightest people of our generation from pursuing their passion projects. Projects that might change the world.

What better way than to ask the advice of Entrepreneurs - all under 35 (often even younger) - how they made the transition from a corporate career to becoming a founder, co-founder, or entrepreneur.

SIGNAL #1

You have a hunch and it won’t go away.

We recently ran a Q&A event that included Benjamin Depraz-Brenninkmeijer who went from working as an investment banker in Paris to founding his own leadership coaching business in 2015. At the same time, Benjamin also joined iDiscover360 as Director of Business Development and Head of Coaching.

We asked him how he took his first step into founding his own startup.

“For me, from idea to action, it's more like in Matrix. Follow the white rabbit. There's something that emerges, like a desire or a hunch, or just a discomfort or frustration of where you are now. Then, it's just more like keep following the thread and see where it goes. It's just a series of actions that don't make sense when you start. They only make sense much later on.”

This is a response we’ve come across a lot. Often, an idea or hunch is sparked by questioning your own experiences. Work, hobbies, lifestyle. Could I do this differently? Could I do this better? Why doesn’t this already exist?

In a recent interview with Gian Powers - who quit PWC to found TLC Lions - he told us how his initial idea came from listening to the complaints of his colleagues.

"I started writing down all of those problems every day and finding a solution to try and come up with new ideas and actually got rid of negativity and it was [the negative comments] actually fuelling my ideas.”

Whilst that hunch might not yet be a fully validated business idea, it’s something that you can begin to explore and begin to build a better understanding of before you attempt to turn it into something bigger.

Naturally, if you have a hunch it’ll keep springing up and demanding your attention and you should trust this instinct, do the research, start to understand if people might be interested in your solution to their problem.

It’s as important to know that it doesn’t have to be fully formed as it is to recognise that this might be your entrepreneurial call to action.

TLDR: Got a hunch about a problem that no one else is solving? Then it’s probably the foundation of a great startup idea.

SIGNAL #2

You’re comfortable resigning yourself to the unknown

Abbie Morris, who formerly worked for the ethical policy and communications consultancy; AEQ Global and is now the Co-Founder and CEO of Compare Ethics, recently shared this nugget of wisdom:

“Honestly, you’re never going to know if it’s the right time [or if you’ve found the right idea] because markets change so quickly.”

Her practical advice was this.

“Be really scientific… What does good traction look like for your audience?...You have to be 100% sure that the product your building is relevant for the market.”

What Abbie was outlining for us was how she wasn’t going to commit to her solution, only to the problem she was trying to solve. Essentially, she has resigned herself to delivering the best product for her market, whatever that might be.

This opinion was echoed by Alex Fahie, a former investment manager who founded Ethical Angel.

“It's never going to be what you think it's going to be. If you have an idea and a passion and you see it through, it will become something. It might not be what you want it to be. It might not happen in the timeframe that you think it's going to. I wouldn't be worried about it. What's the worst that could actually happen?”

If you’re ready to resign yourself to pursuing an idea that you’re passionate about then it’s also important to resign yourself to the unexpected, to throwing away countless solutions to find the best fit for your market.

Interestingly, Abbie and Alex both underline an often misunderstood element of the Startup world. The purpose of most startups is to very rapidly attempt to discover a commercially viable solution to a problem.

It’s easy to look at the Facebook’s and AirBnB’s of the world and associate the word Startup with successful business idea. Honestly, you’ll be doing yourself a favour to start thinking of startups as the sandbox in which to rapidly explore solutions. A stepping stone on the way to becoming a viable, scaleable, profitable business.

Steph Newport-Booth, Founder of GoSweat, and former Aldi Manager outlined the mentality that helped her to make the transition into an entrepreneurial career.

“I was very young and very naive and I thought there was a problem. I thought I could tackle it. I guess it's the same, really. What is the worst that could happen? Or maybe not even thinking what's the worst that could happen, but what's the best that could happen? I'm a really big believer in faith, not necessarily like religious faith, but faith in people that you build around you, and even yourself.”

Steph knew that if she embraced the unknown with confidence and a positive attitude that she would succeed. Of course, It’s easy to tell someone “have confidence” and “be positive”. What’s important to recognise is that if you already have this mentality - and you’re not precious about your solutions - then you’re probably already a great candidate for diving into an entrepreneurial career.

TLDR: If you’re not precious about your ideas and aren’t waiting for a green light from the universe. Then you should start looking to validate your ideas and build traction.

SIGNAL #3

You’re not seeking anyone’s approval.

This is a really big hurdle for a lot of people that are considering leaving their jobs to pursue an entrepreneurial career.

The people around them - colleagues, family members, friends - are cautious and potentially unsupportive of their entrepreneurial aspirations.

It’s natural to seek the advice and approval of the people you trust the most but often they’re risk averse and encourage you to keep your respectable job.

Benjamin Depraz-Brenninkmeijer found there were two reasons people struggled to support him at first.

"...1 is they care about you and so in their mind they think that whatever you have now is safer, 2, they're projecting whatever their own fears, values and insecurities are onto your decision.”

Ultimately, your support network has - what they think are - your best interests at heart but this can lead to a lot of negativity and uncertainty from the people you trust the most.

Natalia Bojanic, a former PR Director who went on to Co-Found Form, had this exact experience.


“When I was telling my family back in Brazil [about her business idea], I think they thought I needed an intervention … Maybe they thought “she’s going a bit cuckoo! And maybe I was but thank god I did [commit to the idea].”

Natalia’s solution was to find support and positive reinforcement wherever she could.

“In the age that we live, there are books that can be our tribe, podcasts that can inspire us, events. Everywhere I would go. Everything I listened to. I would stick them in my home so that I had a constant reminder for every time someone would bring negativity into what I was doing.”

We think this is great advice. Prepare yourself for negativity and surround yourself with the things - not just people - that give you strength, positivity, and support.

Benjamin Depraz-Brenninkmeijer learned that you shouldn’t begrudge people and that eventually they’ll come around.

“Don't expect them to support you or be pissed off at them for not doing it, because they have a right to think it's not wise, and that's fine, but I think over time, as they see that you're fulfilled, that you're challenging yourself, that you're growing, that you're enjoying the up and down journey, they also start to come down and realise that it was a good thing for you. It's just you have to go there first.”

Steph Newport-Booth discovered that her friends and family would support her whether they liked what she was doing or not.

“I think I'm incredibly lucky that I'm surrounded by people who are like cheerleaders for me and maybe that's because I've got selective hearing, and I only actually listen to what they're saying that goes with what I think, but yes, it's your decision, it's your life, going back to like the biggest thing that would bug me would be thinking about what if.”

Much like Natalia, Steph also prepared herself for negativity and whether through selective hearing or the fear of “what if”, it’s a good idea to start planning to have your ideas questioned and pulled apart by your existing support network.

Abbie Morris had her own solution to combat the negative comments.

“In terms of tangibly what I was doing... I just put in the topic of sustainable fashion [the industry her idea was based in] into Eventbrite. I went to every single event I could find.

Similarly, Gian Powers signed up for every opportunity within his existing company.

I hooked up with the intrapreneur network, entrepreneur network … and got involved with the startup scene at PWC. I went on the intranet and they offered loans to startups. Just shifting my day job to being more around that [what I was interested in as a would be entrepreneur].”

This touches on the fact that becoming a founder or starting an entrepreneurial career does involve a significant shift in lifestyle. The people you’ve collected over the previous period of your life may not be your most vocal supporters BUT you will always find new people that do champion your ideas. You just have to go out and create opportunities to meet them first.

Benjamin Depraz-Brenninkmeijer explained that.

“...you will always have people supporting you, if you challenge yourself, you will always have people who show up to help but not everybody and maybe not the people very close to you [now].”

Joly Fengyang Zou, who left her career as a marketing manager at Microsoft to found SoLocal, also found that she built a new support network after making her transition into entrepreneurship.

“I still have some close friends from my previous company job, but if I look around most of my closest friends are from after I quit my job, because of the similar mindset.”

Being a bit bullet proof. Knowing that you’ll change the minds of the doubters. Having faith that you’ll meet like minded people along the way.

If you’re not seeking the approval of your existing support network, are willing to hunt down ways to surround yourself with positivity, and want to attend every possible event on Eventbrite. Then this is another sign that you might have the mentality to make an outstanding entrepreneur.

TLDR: Whilst you might worry a few people along the way, you’re going to find people that support what you’re doing anyway. So as long as you’re not seeking the approval of your best friend, parents, or colleagues, then you’re going to do great.

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Really quickly, we think these are three valuable signs that you already have the mindset to make it as an entrepreneur. Being curious, taking risks, acting on instinct, and not looking for other people to give you a green light. These are some of the entrepreneurial skills that are often overlooked.

If you’re not there yet, that’s okay too.

People aren’t born entrepreneurs, so you can make plans, and map out smaller steps to build up to point where you can say yes to each of these signals.

As per the advice of the founders we interviewed.
Here are some things you can do today:

  1. See what opportunities are already available to you
  2. Start attending entrepreneurial events and meeting people
  3. Focus on a problem that needs solving not a specific product
  4. Start turning other people’s complaints into ideas and solutions

More than anything we hope this gets you one step closer to quitting your job to do something you’re really passionate about.

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