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Entrepreneurs: what advice would you give yourself 10 years ago?

We are generally very quick to give advice to others, but don’t always follow this advice ourselves. In a recent post, Brad Feld warned against the dangers of short-term entrepreneurial thinking and explained why he is looking forward to 2025. Fast Company shared 6 things you’re doing that you’ll seriously regret in 10 years. So what advice would you give your younger self if you could go 10 years back in time?

Personally, I would go tell myself: “It is great to have a sense of urgency to act, but the [Real Option] to wait a bit should also be considered… Strategically doing nothing about a situation for a little longer can change the situation, as new information transpire. (Oh, and the winning SA Lotto numbers for the R102-million jackpot on 2011–06–03 are: 6, 30, 31, 33, 36. Powerball 16)”.

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We recently had some South African entrepreneurial thought leaders on a unique #VentureTrain networking and brainstorming event between Johannesburg and Cape Town where we unpacked this issue in context. Most of the self-administered advice dealt with taking more calculated risks, setting higher goals, mastering your art, trusting your gut instinct and being productive while not being so hard on yourself… Here are some interesting takes:

“Don’t stick to someone else’s mould just to please people. Find out what your passions are quickly. Be curious. Unlearn the traditional. Taking a risk will only get harder every day you wait. You have more potential than even you realise. And time is going to fly, do it now and be productive every single day.” — Julia Woods: Entrepreneur & business building strategist.

“Calm down, don’t put so much pressure on yourself and everyone all the time. Keep believing that success will come from good work, creating value and seeing the best in the world.” — Glenn Gillis: Sea Monster Entertainment.

“Buy those Naspers shares, run more, part-time anything never works. Understand a person’s motivation rather than their stated intentions. The rules are made up.” — Brett Commaille: AngelHub Ventures. [Don’t beat yourself up Brett, you would have only made 19x your money on Naspers excluding dividends re-invested ;-)].

“Set higher goals, then take life less seriously!” — Ryan Stramrood: Extreme ice swimmer, motivational speaker and advertising sales entrepreneur.

“You don’t have to be perfect. Be brave, take risks. Others might not understand, you might not be popular for doing it, but trust your gut and do it anyway.” — Arlene Mulder: training world-class software engineers at WeThinkCode_ .

“Stop worrying so much about everything. You’re on the right track, just keep going.” — Aisha Pandor: Cleaning Services tech startup: SweepSouth.

“Use the information about your uniqueness & strengths to choose your lane, stick to it, refine it and be the master of your own lane.” — Neo Maruatona: Niche investment & advisory company: Maya Group. [This strategy seemed to work well for Caster Semenya at the Rio Olympics].

“Get out of your cocoon and build a network.” — Floris Buys: Telkom Digital.

“Most value is created at the beginning and sale of a business. We spend most of our time building a business, but far too little on those crucial stages. Take some time, in the beginning, to research and plan the business model, financials, risks, first 100 days, growth strategy, key people, governance and exit plan before you start (i.e. before the chaos erupts). Before the sale of your business, focus on working yourself out of the business and spend at least a year preparing for the exit (or if you are not able to, give/sell some equity to an angel or VC who is an expert at exits to prepare your business for the exit. They will pay for themselves many times over).” — Abraham van der Merwe: Investor and Entrepreneur; Frogfoot Networks.

“Follow your instincts [they are more accurate than you believe] and don’t be scared to fail.” — Westleigh Wilkinson: OPEN Collaborative City Workspace/ Workshop 17.

“Lightly document what you’re doing, as well as how and why you’re doing it. Not everything. Just the big things. Keep in touch with as many of the lovely and interesting people you meet in a way that means something to both of you.” — Andy Skinstad: FONK Mobile.

“Back yourself to succeed, don’t get too hung up on the 10-year plan but rather concentrate on doing what you do today to the best of your ability.” — Gavin Rush: R&D Manager at global life sciences company: Kapa Biosystems.

What advice would you give yourself 10 years ago? Or today to ensure you have no regrets in 2026?

This post originally appeared on Medium and has been republished with permission from the author.

Feature image: cornflakegirl_ via Flickr.

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