So You Sold Your Business—Now What?

For entrepreneurs, building out and scaling up an enterprise can be among life’s most fulfilling and rewarding experiences. At some point however the matter of exiting the business, whether through family succession or through an outright sale, will arise. While such an exit, particularly in the case of a sale, can be highly lucrative and open up a world of newfound freedom and opportunity, it may also present challenges around personal identity, direction, and financial continuity. This article explores these topics and highlights the very human and emotional aspects along with the financial considerations that this kind of transition may bring about.

The Emotional Impact of Selling a Business

Having spent years wrapped up in running and growing your business while facing and overcoming challenges, the sale of your business can bring about a feeling of internal culture shock, with many of these familiar tasks and objectives no longer on the docket, perhaps replaced with a newfound abundance of time which you must now decide how to spend. It is almost ironic that this freedom, both personally and financially, can feel paralyzing and confusing; however, these feelings can be allayed with some reflection and planning.

In the weeks leading up to the sale of the business, or perhaps following it, you may wish to set aside one day per week to experimenting with new hobbies, reconnecting with the past, or just reflecting on your personal goals outside of the business. This reflection can include the impact you would love to have on your community, family, or an important cause you care about. As much as the exit from business leadership can bring about questions around identity and purpose, with some reflection this transition can also set in motion the pursuit of non-entrepreneurial goals and uses of time that took a backseat years ago—ambitions that have patiently awaited their turn to take center stage while building and growing your enterprise was the all-encompassing priority.

The Financial Impact of Selling a Business

The sale of a business is often a very financially rewarding experience and creates the unique opportunity to diversify wealth in the pursuit of your goals. During the time that you were operating your business, you may have found that your wealth was very much concentrated within it, with the enterprise often forming the centerpiece of your personal balance sheet. Upon sale, you now have the ability to diversify as the proceeds are paid out to you and the value of the business becomes liquid.

Just as owning your business allowed you to generate cash flow while retaining your capital in the business itself, you may wish to explore investments that enable you to mimic this experience. For instance, investing in a diversified portfolio of dividend-paying stocks could provide a stream of continuous, independent cash flow while your original capital remains invested and participating in the growth of the market. In fact, you may have already enjoyed the tax benefits of dividend-based income as a business owner, so an approach such as this may be at least somewhat familiar as the underlying principle remains much the same—participating in the earnings of a business through its cash flow in a tax-preferential way while keeping your ownership stake intact. Taking a dividend-paying equity approach or planning out your “retirement” income stream will likely be a top priority.

In cases where the wealth resulting from the disposition of your business may exceed your own personal needs, you may want to explore the impact of each potential allocation of this surplus wealth. Going through a comprehensive financial planning process can help you ascertain what portion of your net worth is indeed superfluous to your present needs, so that planning its allocation can begin. Through some personal reflection on values, you may focus on philanthropy and impact investing, or perhaps on clearly defining a thoughtful legacy to set your children or other family members up for long-term success.

Quantifying the impact that you wish to have in each area of focus may take time and careful planning, perhaps in consultation with a few professional advisors should you require guidance, but the end result will very likely be fulfilling. The execution of the strategies you develop may very well provide the continuity of purpose that you would want for yourself through this important transition.


Bloom Investment Counsel, Inc. is a well-established Toronto-based independent, privately-owned boutique investment management firm providing customized, actively managed, Canadian and U.S. dividend-paying portfolios for wealthy individuals, family offices, foundations, corporations, institutions and trusts.

Founded in 1985, Bloom has experience in managing in excess of $2.5B in assets over the years. We believe that generating independent cash flow is central to the success of our clients’ portfolios because it provides capital for the present day, if needed, while continuing to preserve and build wealth for the future.

Follow Bloom Investment Counsel, Inc. on LinkedIn to stay up to date on our most recent articles.

This content is provided for general informational purposes only and does not constitute financial, investment, tax, legal or accounting advice nor does it constitute an offer or solicitation to buy or sell any securities referred to. Individual circumstances and current events are critical to sound investment planning; anyone wishing to act on this content should consult with his or her financial partner or advisor.

Leave a Reply

Your email address will not be published. Required fields are marked *


© 2022 Bloom Investment Counsel, Inc. All rights reserved. E & O E.

Powered by W3Schools