Coming to startup land as a thirty-something mother of two has been a fun journey. After a 15-year corporate career, one successful lifestyle business established and my fair share of Big Life Challenges under my belt, this new gig was just gonna be more of the same right? Nothing it can throw at me can be that new/hard/challenging right? Right???

Here is what I’ve learnt about the unique and special challenges startup entrepreneurship poses in mid-life:

  1. It’s all consuming. Looking at our lifestyle business and looking at our startup the contrast is striking. I’m not saying lifestyle businesses are easy. But lifestyle to me means ‘here’s a business that we know works and we choose to keep it at a size that suits us’. In contrast startup to me means ‘what are we even building and how is it going to work and who’s writing the manual and bringing the biscuits?’ There is no limit to how much time you can spend thinking about these problems. My mind is in startup land 90% of my waking and 50% of my sleeping hours. Which when you have a raft of responsibilities to cover outside of ‘work’ can be challenging.
  2. It’s extreme. Emotionally, mentally and physically startup is an extreme experience. If I’m not feeling extremely ‘something’ in any given moment that’s a hint we’re not going fast enough. Out of your comfort zone is also the new normal. This trickles out into other spheres of your life — for example, I now go after more extreme experiences in exercise (took up spin), and in health (became a vegan and a minimalist). The amount of Sriracha I get through is ridiculous. This can’t be a coincidence. But now the things my kids throw at me, the previously extreme moments of the day to day, don’t feel extreme at all. #forthewin.
  3. Most people won’t understand. The number of people who have created something out of absolutely nothing is actually quite small. The world you’re in is alien to probably 99% of the people in your typical mid-life family social setting. Not many people live next door to Katrina Lake. And most people don’t see Mathilde Collin at school drop off. Most people will think you are utterly deluded and/or ask questions like ‘how’s business’ with absolutely no perception of the depths of complexities your brain tries to compute to answer that question. So you’ll smile and say ‘fine’. Every time. And feel a bit more like an outsider. Every time.

All this can at first make you feel like this isn’t for you, or your priorities are off, or your work-life balance is wrong, or that you’re totally alone. None of this is true, and here’s what you can do about it:

  1. Pick a problem you really, really care about solving. My passion for our cause is driven by the impact we’re having on people. I think about this every day and it makes me feel positive, motivated and fueled for the journey.
  2. Accept that your mind is going to want to be elsewhere, a lot. So concentrate on managing your attention, not your time — hours are no longer your relevant unit of operation. Work no longer sits in a time-based silo. Instead, mindfulness and concentrating on being present when you want to are new skills you need to develop. Being fully present with family for half the time suits me better than being half present for twice the time.
  3. Surround yourself with people who get it. This might be in person, like through meetups, master-mind groups, incubators or co-work spaces. Or remotely via podcasts. Listen at 1.5x speed or higher for max productivity (extreme experience seeking kicking in again). But whatever it is, find someone to say ‘me too!’ to. If you’re ever stuck tweet me and I’ll say ‘me too!’ back.
  4. Remember your middle-aged superpowers. According to the World Economic Forum, mid-life entrepreneurs are far more successful than younger ones –in terms of business survival rates, ongoing growth and exits. So back yourself; getting through all those uniquely mid-life challenges was worth it after all — you’ve got grit, you’ve got perspective and you’ve got a ludicrously high pain threshold. Use it well.


Lisa is co-founder and CEO at HellyHolly where they make Our Canary, a chat-first productivity tool that uses bots to help busy people stay organised, work together and get stuff done. Our Canary is developed through user-centred design, and turns your existing productivity tools into a proactive, personalised digital assistant. Lisa also advises in corporate venturing where she specialises in helping corporates identify, evaluate and develop digital product and service businesses.

Geraint Evans