Should you quit your job to start a business?

Should you quit your job to start a business?

Josh Hollander, President & CEO of Horton International North America recently met with David Bruno to talk about “Professional Pivots”. We’re delighted to share David’s article with you here.

You can also find the article and connect with David on LinkedIn.


Should you quit your job to start a business?


Summary: People in their 40s and 50s inside corporations have built up tremendous domain expertise and in combination with new technologies and business models they are well-positioned to still do some pretty incredible things. This article will help manage your Professional Pivot like a boss.

Was that it? Are you done? Made money for 25 years, managed some people, paying for kid’s tuitions, then golf? Booooooring.

I had a talk with Josh Hollander, President & CEO of Horton International North America, about how to leverage your domain expertise in a “Professional Pivot” and actually do more of what you love. Today’s article and linked podcast will show you how to start taking those first steps while not endangering your financial or family situation.

1. Becoming self-aware: You are stuck!

Many of us have found a sense of higher purpose over the years, becoming deep domain experts in our industry. Whether actuary, accountant, lawyer, program manager the trend is almost always the same: Boredom with the day-to-day routine doing what you were originally trained to do as a specialist – because you have come to understand the big picture and want to help accelerate your industry into the future.

There are are a huge number of subject matter experts, high achievers well-tuned to corporate success, who reach a certain level and then get stuck there for many years. This can even happen to a CEO/COO/CFO leading hundreds or even thousands of people. How do you start to make an impact in a different way? You can see the transformational change in your industry, and your organisation leveraging technology in new ways. Realize you are not alone. Most 40-50-somethings I’ve met who are still working in an office environment are bored out of their minds.

2. Identifying your higher purpose

Is the reason you get up and go to work still just making cash flows or has it shifted to something else, something bigger and more meaningful?

“If you believe you can add value there are opportunities to explore where your organization is making change and how you can contribute to that.” – JH

For example right now many companies are building up that new golden tower of “data science”. You can’t get out of any meeting without someone saying “Machine Learning” and AI. Now what do those data science guys know about “our” customers, our products, our industry??

Domain expertise of knowing insurance for can help the data scientists develop and tailor and add value. Even if you’re not a data scientist writing code the company needs people who can construct a business model and provide those other support functions that will bring innovation to life and new changes into an organization. Those new data science guys won’t win without YOU.

3. Creating new habits

Many folks these days seem to want to become influencers. Write a book. Mentor startups. Become an investor. But what did the few success stories actually do to get started? How did they break out of their organisations and create a wider platform for doing good?

Our advice is to start by seeking new internal and external interactional opportunities. You don’t have to seek a job change specifically. By external we mean go to local meetups, fintech, insuretech, incubators and accelerators, industry groups – attend and see what type of activities are taking place, do some mentoring for early-stage organisations. Internally, if you have a specific idea bubble that up to senior management, get involved with your innovation team, HR may also have resources available to help build your skills.

Many companies are trying to keep up with change by launching innovation challenges. You may also see senior management start hiring talent from the outside with different skill set, more technologically savvy. Organizations face competitive pressure from new areas, as digital winners like Amazon keep setting new bars for customer satisfaction.

4. Adding new stimuli, people and locations

Horton International actually moved its office into the startup ecosystem at Upward Hartford in order to be in the middle of the transformation and change process transforming Insuretech and advanced manufacturing in Connecticut. Josh uses the platform to get to know the Professional Pivoters and bring talent into new spaces like FinTech and Insuretech around the region including Hartford, New York and Boston.

The lesson from Josh is, if you work in a small-medium enterprise then consider shifting a part of your organization right into then middle of where you see the change happening. If you’re part of a large corporate, speak passionately and repeatedly to the executive team about landing that sponsorship to become a corporate partner to your local ecosystem coral heads, whether a startup incubator, accelerator or any hub where you see the change attracting new talents to work in “your” domain expertise.

5. Developing your Side Hustle

Learning takes place in new ways. If you are expanding your network and identifying resources that could be useful for the organization, that’s a positive overall. You could begin mentoring, attending external events, attending an online seminars – but you will have to start doing new things to re-boot your learning.

“Career development means Side Hustle. You can do things to show you have the enthusiasm and mindset to leverage your experience in new ways.” – JH

The highest chance is that developing the new habits described above will lead you to a new, better gig inside your existing organisation. It will also likely open doors to outside opportunities you never knew you had, which is useful for your self-confidence and market worth check inside your organisation.

6. Going rogue: The Wanna-be Entrepreneur

“Serial entrepreneur”. Ok get that off your CV right away unless you have the chops to prove it (eg. have personally been involved in multiple exits of businesses you helped build for tangible commercial value). There is sop much rhetoric used about being an entrepreneur that it’s mostly a turn-off and the professionals see through it quickly.

If that idea of yours is really so big and pervasive that you want to try to launch it – we recommend to start to build it outside your company in low-risk stealth modus using the amazing online resources available today. You can use Google Cloud, AWS, external design shops and marketeers to help launch your new thing. I highly recommend joining a local program to add structure and new perspectives, for example a MakerSpace, Incubator or Accelerator.

Don’t throw all your family silver into one idea when the reality is there will generally be unexpected bumps along the way. Start small, validate your hypotheses, be prepared to start and stop multiple times, and keep the resources in place to keep progressing along this journey for the long term.

“I wouldn’t quit your day job right away. Leverage the resources outside your office to build and test your idea.” – JH

Latest Post

Insights To Your Inbox

Sign Up to Receive the latest news and leadership insights.

Sign up to receive the latest news and leadership insights