Making the Leap

Starting a business after years in corporate – things I wish I’d known 20 years ago

Making the Leap: Starting a Business After Years in Corporate

This article is a summary of the things I wish I’d known 20 years ago when I left my corporate job and was starting a business. I hope you find these suggestions and encouragement helpful as you find your own footing and embrace the challenges of business ownership.

Key Lessons and Strategies

Transitioning from a successful corporate career to starting a business on your own is both exhilarating and daunting. It’s a move that demands courage, clarity, and a fresh perspective on how to leverage your experience. For those embarking on this journey, particularly after years in a prestigious firm, there are key lessons and strategies that can smooth the transition and set you up for success. Here’s a guide inspired by the advice I recently shared with a colleague about to make the move.

And, you might also want to consider whether you are an Inside Cat or an Outside Cat before you get too far along!

Making the Leap - 1 - use your credentials to open doors

1. Start Building Momentum Before You Leave

If you still have time before officially launching your business, use it wisely. Start cultivating relationships, scheduling meetings, and establishing your presence in your target industry. The relationships and opportunities you nurture now will serve as a launchpad once you’re on your own.

Proactive Steps

  • Attend industry conferences to position yourself as a thought leader.
  • Reach out to your network with a clear message about your new venture and its value.
  • Start building a pipeline of potential clients who see you as a trusted advisor before your corporate affiliation changes.
Making the Leap - 2 - Tie Everything Back to Client Pain Points

2. Tie Everything Back to Client Pain Points

Every new business must solve a problem. The success of your business depends on how well you link your offerings to the specific, tangible problems your target clients are actively seeking to solve. These concerns highlight universal pain points for business owners navigating uncertainty. Position your offerings as the solution to these pressing questions. I believe there is a correlation between the severity of the pain point you address and your likelihood of success.

Practical Application

The burning business questions your target clients are worrying about can also serve as the foundation of your marketing strategy. Make it clear how your services alleviate these anxieties and enable your clients to thrive in the face of disruption. For example, if you’re helping businesses integrate AI, emphasize how your solutions protect them from disruption or give them a competitive edge. Focus on outcomes, not just capabilities or how you would conduct the project.

Making the Leap - 3 - 80/20 Sales and Marketing

3. Focus on High-Probability Opportunities

It’s tempting to pursue every lead when you’re starting out, but not all prospects are created equal. Spending too much time chasing “maybe” clients can drain your resources and dilute your focus. I laugh when I look at the list of prospects I kept when we first started – with my experienced eyes I can now see that only a few were ever potential clients.

Key Insight

I am a big fan of the principles in 80/20 Sales and Marketing by Perry Marshall. This approach emphasizes identifying and prioritizing the small percentage of prospects most likely to convert, rather than spreading yourself too thin across less promising leads. By focusing on high-probability opportunities, you’ll conserve your energy for efforts with the highest ROI. The 80/20 rule applies to itself; the 20% of the 20% will produce outsized returns. Businesses have been built on just a few critical relationships and knowing how to identify and cultivate those is likely to be a big part of your success.

Making the Leap - 5 - Embrace the Power of Speaking Engagements​

4. Embrace the Power of Speaking Engagements

Nothing boosts credibility and visibility faster than being seen as an expert. Speaking at conferences or industry events puts you in front of potential clients and reinforces your authority.

Pro Tip

Leverage your current corporate role to secure these opportunities while your name is still tied to an established brand. Once you’ve made the leap, the relationships and recognition you’ve cultivated will help you stand out in a competitive market. Unfortunately, newly established businesses and their founders are not as sought-after for these speaking engagements so you will likely have a much harder time securing those in the first few years after you launch (unless you get enough speaking gigs to be sought after).

Final Thoughts: Confidence with a Plan

Starting a business after years in a corporate role is a bold move, but your corporate experience has equipped you with tools and insights to succeed. By focusing on clear client pain points, prioritizing high-conversion opportunities, and leveraging your existing credentials, you can create a business that thrives.

Remember: the transition is as much about mindset as strategy. Believe in the value you bring and be disciplined in how you spend your time and energy. Success will follow.

Are you embarking on a similar journey? Share your story or reach out with your questions—I’d love to hear from you.

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Rob Toomey

Presidente e cofundador da TypeCoach

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